CyanoMetDB_ID,Name,Synonym,Synonyms,Compound_Class,Molecular_formula,Molecular_weight,Monoisotopic_mass,SMILES ,InChI,InChlKey,IUPAC_name,PubChem_CID,DTXSIDs,DOI_No1,Url_No1,"Reference_Text_No1 Title; Journal; Vol,; Issue; pages; year; type; DOI; author1; authors2; etc.",Genus,Species,Strain,Field sample,Notes
CyanoMetDB_1782,"[D‐Asp³,DMAdda5]MCLA",,,Microcystin,C44H63N7O12,882.01,881.4534708,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C44H63N7O12/c123(2)193342(59)5034(44(62)63)2236(53)4527(6)39(56)4731(161524(3)2025(4)35(52)2130131110121430)26(5)38(55)4832(43(60)61)171837(54)51(9)29(8)41(58)4628(7)40(57)4933/h1016,20,23,2528,3135,52H,8,1719,2122H2,17,9H3,(H,45,53)(H,46,58)(H,47,56)(H,48,55)(H,49,57)(H,50,59)(H,60,61)(H,62,63)/b1615+,2420+/t25,26,27,28+,31,32+,33,34+,35/m0/s1",YEECPBMSOJOCFKBSBXEUFZSAN,"(5R,8S,11R,15S,18S,19S,22R)18((1E,3E,5S,6S)6hydroxy3,5dimethyl7phenylhepta1,3dien1yl)8isobutyl1,5,15,19tetramethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",146684713,,10.1186/147121487183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/147121487183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/147121487183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Hapalosiphon,hibernicus,[Hapalosiphon hibernicus]BZ31,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1783,[D‐Asp³]MCVA,,,Microcystin,C44H63N7O12,882.01,881.4534708,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C44H63N7O12/c123(2)3742(58)4933(44(61)62)2235(52)4527(6)39(55)4731(171624(3)2025(4)34(6310)2130141211131530)26(5)38(54)4832(43(59)60)181936(53)51(9)29(8)41(57)4628(7)40(56)5037/h1117,20,23,2528,3134,37H,8,1819,2122H2,17,910H3,(H,45,52)(H,46,57)(H,47,55)(H,48,54)(H,49,58)(H,50,56)(H,59,60)(H,61,62)/b1716+,2420+/t25,26,27,28+,31,32+,33+,34,37/m0/s1",RBZCKDFHDZZPOQFTJZKGJUSAN,"(5R,8S,11R,15S,18S,19S,22R)8isopropyl18((1E,3E,5S,6S)6methoxy3,5dimethyl7phenylhepta1,3dien1yl)1,5,15,19tetramethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",146684714,,10.1186/147121487183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/147121487183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/147121487183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Hapalosiphon,hibernicus,[Hapalosiphon hibernicus]BZ31,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1784,MCVA,,,Microcystin,C45H65N7O12,896.04,895.4691208,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C45H65N7O12/c123(2)3643(59)5137(45(62)63)27(6)39(55)4628(7)40(56)4832(181724(3)2125(4)34(6411)2231151312141631)26(5)38(54)4933(44(60)61)192035(53)52(10)30(9)42(58)4729(8)41(57)5036/h1218,21,23,2529,3234,3637H,9,1920,22H2,18,1011H3,(H,46,55)(H,47,58)(H,48,56)(H,49,54)(H,50,57)(H,51,59)(H,60,61)(H,62,63)/b1817+,2421+/t25,26,27,28,29+,32,33+,34,36,37+/m0/s1",IFVHFRYOHFIXJAJDFQIOQSSAN,"(5R,8S,11R,12S,15S,18S,19S,22R)8isopropyl18((1E,3E,5S,6S)6methoxy3,5dimethyl7phenylhepta1,3dien1yl)1,5,12,15,19pentamethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",146684715,,10.1186/147121487183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/147121487183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/147121487183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Hapalosiphon,hibernicus,[Hapalosiphon hibernicus]BZ31,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1785,[DAsp3]MCLA,,,Microcystin,C45H65N7O12,896.04,895.4691208,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C45H65N7O12/c124(2)203443(59)5135(45(62)63)2337(53)4628(6)40(56)4832(171625(3)2126(4)36(6410)2231141211131531)27(5)39(55)4933(44(60)61)181938(54)52(9)30(8)42(58)4729(7)41(57)5034/h1117,21,24,2629,3236H,8,1820,2223H2,17,910H3,(H,46,53)(H,47,58)(H,48,56)(H,49,55)(H,50,57)(H,51,59)(H,60,61)(H,62,63)/b1716+,2521+/t26,27,28,29+,32,33+,34,35+,36/m0/s1",IEIRNZAKAQISQHKEGFNAPLSAN,"(5R,8S,11R,15S,18S,19S,22R)8isobutyl18((1E,3E,5S,6S)6methoxy3,5dimethyl7phenylhepta1,3dien1yl)1,5,15,19tetramethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",146683852,,10.1021/ac051556d,https://pubs.acs.org/doi/10.1021/ac051556d,"Identification of Microcystin Toxins from a Strain of Microcystis aeruginosa by Liquid Chromatography Introduction into a Hybrid Linear Ion TrapFourier Transform Ion Cyclotron Resonance Mass Spectrometer;Analytical Chemistry;78;2;;2006;journalArticle;10.1021/ac051556d;Diehnelt, Chris W.; Dugan, Nicholas R.; Peterman, Scott M.; Budde, William L.",Microcystis,aeruginosa,[Microcystis aeruginosa]B2666,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1786,[Dha7]MCLA,,,Microcystin,C45H65N7O12,896.04,895.4691208,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C45H65N7O12/c123(2)203443(59)5237(45(62)63)27(6)39(55)4729(8)41(57)4932(171624(3)2125(4)35(6410)2231141211131531)26(5)38(54)5033(44(60)61)181936(53)4628(7)40(56)4830(9)42(58)5134/h1117,21,23,2527,2930,3235,37H,7,1820,22H2,16,810H3,(H,46,53)(H,47,55)(H,48,56)(H,49,57)(H,50,54)(H,51,58)(H,52,59)(H,60,61)(H,62,63)/b1716+,2421+/t25,26,27,29,30+,32,33+,34,35,37+/m0/s1",RMWLEIURXQBESLOOMCYYCHSAN,"(5R,8S,11R,12S,15S,18S,19S,22R)18((1E,3E,5S,6S)7(cyclohexa2,4dien1yl)6methoxy3,5dimethylhepta1,3dien1yl)8isobutyl5,12,15,19tetramethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",146684716,,10.1186/147121487183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/147121487183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/147121487183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Hapalosiphon,hibernicus,[Hapalosiphon hibernicus]BZ31,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1787,[DMAdda5]MC‐LA,,,Microcystin,C45H65N7O12,896.04,895.4691208,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C45H65N7O12/c123(2)203443(60)5137(45(63)64)27(6)39(56)4628(7)40(57)4832(171624(3)2125(4)35(53)2231141211131531)26(5)38(55)4933(44(61)62)181936(54)52(10)30(9)42(59)4729(8)41(58)5034/h1117,21,23,2529,3235,37,53H,9,1820,22H2,18,10H3,(H,46,56)(H,47,59)(H,48,57)(H,49,55)(H,50,58)(H,51,60)(H,61,62)(H,63,64)/b1716+,2421+/t25,26,27,28,29+,32,33+,34,35,37+/m0/s1",SPMKPKQNTFKRRNNLLIVGSUSAN,"18((1E,3E)6hydroxy3,5dimethyl7phenylhepta1,3dien1yl)8isobutyl1,5,12,15,19pentamethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",155802328,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",n.a.,n.a.,n.a.,"field sample, Hartbeespoort Dam (25°44′05.34″S, 27°52′08.64″E), Pretoria, South Afrika","This compound was not linked to an identified cyanobacterial species in the cited study. Microcystis aeurginosa dominanted the cyanobacterial community under study. A combination of LCMS2 and thiolderivatisation were used for tentative identification in a Hartbeespoort Dam (South Africa) sample. MS2 available in article, though without putative annotation of the product ions."
CyanoMetDB_1788,[DMAdda5]MCLR,O‐demethyl‐MC‐LR,,Microcystin,C48H72N10O12,981.15,980.5331181,C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)O)/C,"InChI=1S/C48H72N10O12/c125(2)223645(66)5739(47(69)70)29(6)41(62)5434(1613215148(49)50)44(65)5333(181726(3)2327(4)37(59)2432141110121532)28(5)40(61)5535(46(67)68)192038(60)58(9)31(8)43(64)5230(7)42(63)5636/h1012,1415,1718,23,25,2730,3337,39,59H,8,13,16,1922,24H2,17,9H3,(H,52,64)(H,53,65)(H,54,62)(H,55,61)(H,56,63)(H,57,66)(H,67,68)(H,69,70)(H4,49,50,51)/b1817+,2623+/t27,28,29,30+,33,34,35+,36,37,39+/m0/s1",IYDKWWDUBYWQGFZVCLVCPPSAN,"(5R,8S,11R,12S,15S,18S,19S,22R)15(3((diaminomethylene)amino)propyl)18((1E,3E,5S,6S)6hydroxy3,5dimethyl7phenylhepta1,3dien1yl)8isobutyl1,5,12,19tetramethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",101641983,,10.1021/jo00029a016,https://pubs.acs.org/doi/abs/10.1021/jo00029a016,"Identification of 12 hepatotoxins from a Homer Lake bloom of the cyanobacteria Microcystis aeruginosa, Microcystis viridis, and Microcystis wesenbergii: nine new microcystins;The Journal of Organic Chemistry;57;3;;1992;journalArticle;10.1021/jo00029a016;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Stotts, Richard R.; Dahlem, Andrew M.; Beasley, Val R.; Carmichael, Wayne W.; Evans, William R.",Microcystis,aeruginosa,n.a.,,"Field samples collected from Homer Lake (Illinois) that consisted primarily of M. aeruginosa, plus smaller quantities of M. uiridis and M. wesenbergii."
CyanoMetDB_1789,[D‐Asp³]MC‐LV,,,Microcystin,C47H69N7O12,924.09,923.500421,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)C(C)C)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H69N7O12/c125(2)213544(60)5236(47(64)65)2438(55)5340(26(3)4)45(61)4933(181727(5)2228(6)37(6611)2332151312141632)29(7)41(57)5034(46(62)63)192039(56)54(10)31(9)43(59)4830(8)42(58)5135/h1218,22,2526,2830,3337,40H,9,1921,2324H2,18,1011H3,(H,48,59)(H,49,61)(H,50,57)(H,51,58)(H,52,60)(H,53,55)(H,62,63)(H,64,65)/b1817+,2722+/t28,29,30+,33,34+,35,36+,37,40/m0/s1",OFWRHWYXGMTEEECTLQKDTCSAN,"(5R,8S,11R,15S,18S,19S,22R)8isobutyl15isopropyl18((1E,3E,5S,6S)6methoxy3,5dimethyl7phenylhepta1,3dien1yl)1,5,19trimethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",146684717,,10.1186/147121487183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/147121487183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/147121487183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Hapalosiphon,hibernicus,[Hapalosiphon hibernicus]BZ31,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1790,MCLAba,"MCLAbu, MC‐LAib",,Microcystin,C47H69N7O12,924.09,923.500421,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H69N7O12/c1123344(60)5034(191826(4)2327(5)37(6611)2432161413151732)28(6)40(56)5135(46(62)63)202138(55)54(10)31(9)43(59)4830(8)42(58)5236(2225(2)3)45(61)5339(47(64)65)29(7)41(57)4933/h1319,23,25,2730,3337,39H,9,12,2022,24H2,18,1011H3,(H,48,59)(H,49,57)(H,50,60)(H,51,56)(H,52,58)(H,53,61)(H,62,63)(H,64,65)/b1918+,2623+/t27,28,29,30+,33,34,35+,36,37,39+/m0/s1",XPANWVSGPFXZCMGZGPOYOASAN,"(5R,8S,11R,12S,15S,18S,19S,22R)15ethyl8isobutyl18((1E,3E,5S,6S)6methoxy3,5dimethyl7phenylhepta1,3dien1yl)1,5,12,19tetramethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11,22dicarboxylic acid",146683898,,10.1046/j.14401835.1998.00119.x,https://onlinelibrary.wiley.com/doi/abs/10.1046/j.14401835.1998.00119.x,"Detection of microcystins from cyanobacterial water blooms in Thailand fresh water;Phycological Research;46;s2;;1998;journalArticle;10.1046/j.14401835.1998.00119.x;Mahakhant, Aparat; Sano, Tomoharu; Ratanachot, Pannarat; Tong‐a‐ram, Taksawan; Srivastava, Vishal C.; Watanabe, Makoto M.; Kaya, Kunimitsu",Microcystis,aeruginosa,n.a.,,Detected in bloom sample comprising 95% Microcystis aeruginosa (Thailand). Aba = 2aminobutyric acid (not Aib which is 2aminoISObutyric acid)
CyanoMetDB_1791,"[D‐Asp3,D‐MeOGlu6]MC‐LAba ","[DAsp3,DGlu(OMe)6]MCLabu, [D‐Asp3,D‐Glu(OMe)6]MC‐LAba ",,Microcystin,C47H69N7O12,924.09,923.500421,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)OC)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H69N7O12/c1123344(60)5034(191827(4)2328(5)38(6510)2432161413151732)29(6)41(57)5135(47(64)6611)202140(56)54(9)31(8)43(59)4830(7)42(58)5236(2226(2)3)45(61)5337(46(62)63)2539(55)4933/h1319,23,26,2830,3338H,8,12,2022,2425H2,17,911H3,(H,48,59)(H,49,55)(H,50,60)(H,51,57)(H,52,58)(H,53,61)(H,62,63)/b1918+,2723+/t28,29,30+,33,34,35+,36,37+,38/m0/s1",MBMJHNCKPVQQHCDLKNYIFCSAN,"(5R,8S,11R,15S,18S,19S,22R)15ethyl8isobutyl18((1E,3E,5S,6S)6methoxy3,5dimethyl7phenylhepta1,3dien1yl)22(methoxycarbonyl)1,5,19trimethyl2methylene3,6,9,13,16,20,25heptaoxo1,4,7,10,14,17,21heptaazacyclopentacosane11carboxylic acid",146683863,,10.1016/j.envpol.2010.06.018,https://linkinghub.elsevier.com/retrieve/pii/S026974911000237X,"Identification of microcystins from three collection strains of Microcystis aeruginosa;Environmental Pollution;158;9;;2010;journalArticle;10.1016/j.envpol.2010.06.018;del Campo, Francisca F.; Ouahid, Youness",Microcystis,aeruginosa,[Microcystis aeruginosa]UTEX-2666,,Stereochemistry is inferred from other MCs.
CyanoMetDB_1792,"[D-Asp³,Dha7]MC‐YA",,,Microcystin,C47H61N7O13,932.03,931.4327353,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)C[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H61N7O13/c1-25(21-26(2)38(67-7)23-31-11-9-8-10-12-31)13-18-34-27(3)41(58)52-35(46(63)64)19-20-39(56)48-28(4)42(59)50-30(6)44(61)53-36(22-32-14-16-33(55)17-15-32)45(62)54-37(47(65)66)24-40(57)49-29(5)43(60)51-34/h8-18,21,26-27,29-30,34-38,55H,4,19-20,22-24H2,1-3,5-7H3,(H,48,56)(H,49,57)(H,50,59)(H,51,60)(H,52,58)(H,53,61)(H,54,62)(H,63,64)(H,65,66)/b18-13+,25-21+/t26-,27-,29-,30+,34-,35+,36-,37+,38-/m0/s1",MGAZKNAKSAZXDT-QKQRECLSSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-8-(4-hydroxybenzyl)-5,15,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683860,,10.1016/j.jbbm.2005.12.002,https://linkinghub.elsevier.com/retrieve/pii/S0165022X05001739,"Determination of microcystins in environmental samples using capillary electrophoresis;Journal of Biochemical and Biophysical Methods;66;43891;;2006;journalArticle;10.1016/j.jbbm.2005.12.002;Vasas, Gábor; Szydlowska, Dorota; Gáspár, Attila; Welker, Martin; Trojanowicz, Marek; Borbély, George",Microcystis,aeruginosa,[Microcystis aeruginosa]BGSD 243,,Also detected in water samples collected from lake Hármashegy (Hungary). Annotation is putative with stereochemistry of structure presumed from other MC congeners.
CyanoMetDB_1793,[D-Asp3]MC-LL,,,Microcystin,C48H71N7O12,938.12,937.516071,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H71N7O12/c1-26(2)21-36-45(61)51-34(18-17-28(5)23-29(6)39(67-11)24-33-15-13-12-14-16-33)30(7)42(58)52-35(47(63)64)19-20-41(57)55(10)32(9)44(60)49-31(8)43(59)53-37(22-27(3)4)46(62)54-38(48(65)66)25-40(56)50-36/h12-18,23,26-27,29-31,34-39H,9,19-22,24-25H2,1-8,10-11H3,(H,49,60)(H,50,56)(H,51,61)(H,52,58)(H,53,59)(H,54,62)(H,63,64)(H,65,66)/b18-17+,28-23+/t29-,30-,31+,34-,35+,36-,37-,38+,39-/m0/s1",XJIZHUWILPFIOA-IHYVCQHASA-N,"(5R,8S,11R,15S,18S,19S,22R)-8,15-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683853,,10.1021/ac051556d,https://pubs.acs.org/doi/10.1021/ac051556d,"Identification of Microcystin Toxins from a Strain of Microcystis aeruginosa by Liquid Chromatography Introduction into a Hybrid Linear Ion Trap-Fourier Transform Ion Cyclotron Resonance Mass Spectrometer;Analytical Chemistry;78;2;;2006;journalArticle;10.1021/ac051556d;Diehnelt, Chris W.; Dugan, Nicholas R.; Peterman, Scott M.; Budde, William L.",Microcystis,aeruginosa,[Microcystis aeruginosa]B2666,,Stereochemistry assumed based on other MC congeners. MC-LL congener has previously been characterised by amino acid analysis.
CyanoMetDB_1794,[NMe-Ser7]MC-LR,[Mser7]MC-LR,,Microcystin,C49H76N10O13,1013.19,1012.559333,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC\N=C(/N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](CO)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)CC(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H76N10O13/c1-26(2)22-36-45(66)58-40(48(70)71)30(6)42(63)55-34(16-13-21-52-49(50)51)44(65)54-33(18-17-27(3)23-28(4)38(72-9)24-32-14-11-10-12-15-32)29(5)41(62)56-35(47(68)69)19-20-39(61)59(8)37(25-60)46(67)53-31(7)43(64)57-36/h10-12,14-15,17-18,23,26,28-31,33-38,40,60H,13,16,19-22,24-25H2,1-9H3,(H,53,67)(H,54,65)(H,55,63)(H,56,62)(H,57,64)(H,58,66)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,27-23+/t28-,29-,30-,31+,33-,34-,35+,36-,37-,38-,40+/m0/s1",OXWGDZCZZKVNKF-AEBVJMRDSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-((diaminomethylene)amino)propyl)-2-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",10418538,,10.1021/jo00029a016,https://pubs.acs.org/doi/abs/10.1021/jo00029a016,"Identification of 12 hepatotoxins from a Homer Lake bloom of the cyanobacteria Microcystis aeruginosa, Microcystis viridis, and Microcystis wesenbergii: nine new microcystins;The Journal of Organic Chemistry;57;3;;1992;journalArticle;10.1021/jo00029a016;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Stotts, Richard R.; Dahlem, Andrew M.; Beasley, Val R.; Carmichael, Wayne W.; Evans, William R.",n.a.,n.a.,n.a.,,Field samples from Homer Lake (Illinois) (M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii)
CyanoMetDB_1795,[seco‐4/5]MC‐LR,Acyclo‐LR: Adda‐D‐Glu(γ)‐Mdha‐D‐Ala‐L‐Leu‐D‐MeAsp(β)‐L‐Arg‐OH,,Microcystin,C49H76N10O13,1013.19,1012.559333,O=C(O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@@H](N)/C=C/C(/C)=C/[C@H](C)[C@@H](OC)Cc1ccccc1)C(=O)O)C(=O)O,"InChI=1S/C49H76N10O13/c1-26(2)23-37(45(65)58-40(48(70)71)30(6)42(62)55-35(46(66)67)17-14-22-53-49(51)52)57-43(63)31(7)54-44(64)32(8)59(9)39(60)21-20-36(47(68)69)56-41(61)29(5)34(50)19-18-27(3)24-28(4)38(72-10)25-33-15-12-11-13-16-33/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25,50H2,1-7,9-10H3,(H,54,64)(H,55,62)(H,56,61)(H,57,63)(H,58,65)(H,66,67)(H,68,69)(H,70,71)(H4,51,52,53)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",ROJYIJPCSICOBH-GWRQVWKTSA-N,"N2-((2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)-N5-(3-(((R)-1-(((S)-1-(((1R,2S)-1-carboxy-3-(((S)-1-carboxy-4-guanidinobutyl)amino)-2-methyl-3-oxopropyl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxopropan-2-yl)amino)-3-oxoprop-1-en-2-yl)-N5-methyl-D-glutamine",139585701,,10.1016/S0040-4039(00)61500-9,https://linkinghub.elsevier.com/retrieve/pii/S0040403900615009,"Isolation of linear peptides related to the hepatotoxins nodularin and microcystins;Tetrahedron Letters;34;49;;1993;journalArticle;10.1016/S0040-4039(00)61500-9;Choi, Byoung Wook; Namikoshi, Michio; Sun, Furong; Rinehart, Kenneth L.; Carmichael, Wayne W.; Kaup, Anne M.; Evans, William R.; Beasley, Val R.",Microcystis; Dolichospermum/Anabaena,[Microcystis]sp.; [Dolicospermum]sp.,[Dolichospermum flos-aquae]NIVA-CYA 656,,[Choi 1993; Namikoshi 1995] Detected in field samples from Homer Lake (Illinois) (M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii). [Miles 2013] Extracted from culture of Dolicospermum flos aquae NIVA-CYA 656.
CyanoMetDB_1796,MC-FA,,,Microcystin,C49H65N7O12,944.08,943.4691208,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H65N7O12/c1-27(24-28(2)39(68-9)26-35-18-14-11-15-19-35)20-21-36-29(3)42(58)53-37(48(64)65)22-23-40(57)56(8)33(7)46(62)51-32(6)45(61)54-38(25-34-16-12-10-13-17-34)47(63)55-41(49(66)67)30(4)43(59)50-31(5)44(60)52-36/h10-21,24,28-32,36-39,41H,7,22-23,25-26H2,1-6,8-9H3,(H,50,59)(H,51,62)(H,52,60)(H,53,58)(H,54,61)(H,55,63)(H,64,65)(H,66,67)/b21-20+,27-24+/t28-,29-,30-,31-,32+,36-,37+,38-,39-,41+/m0/s1",CQSVGARFVXWFCH-MGMRBZFQSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",139587197,,10.1016/j.phytol.2013.07.011,https://linkinghub.elsevier.com/retrieve/pii/S1874390013001328,"Isolation and structure determination of two new hydrophobic microcystins from Microcystis sp. (CAWBG11);Phytochemistry Letters;6;4;;2013;journalArticle;10.1016/j.phytol.2013.07.011;Puddick, Jonathan; Prinsep, Michèle R.; Wood, Susanna A.; Cary, S. Craig; Hamilton, David P.; Wilkins, Alistair L.",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Absolute stereochemistry defined via Marfey's amino acid analysis
CyanoMetDB_1797,[seco‐1/2]MC‐LR,L‐Leu‐D‐MeAsp(β)‐L‐Arg‐Adda‐D‐Glu(γ)‐Mdha‐D‐Ala‐OH ,,Microcystin,C49H76N10O13,1013.19,1012.559333,O=C(O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](N)CC(C)C)C(=O)O)/C=C/C(/C)=C/[C@H](C)[C@@H](OC)Cc1ccccc1)C(=O)O,"InChI=1S/C49H76N10O13/c1-26(2)23-34(50)44(64)58-40(48(70)71)30(6)42(62)56-36(17-14-22-53-49(51)52)45(65)55-35(19-18-27(3)24-28(4)38(72-10)25-33-15-12-11-13-16-33)29(5)41(61)57-37(47(68)69)20-21-39(60)59(9)32(8)43(63)54-31(7)46(66)67/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25,50H2,1-7,9-10H3,(H,54,63)(H,55,65)(H,56,62)(H,57,61)(H,58,64)(H,66,67)(H,68,69)(H,70,71)(H4,51,52,53)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36-,37+,38-,40+/m0/s1",IENVPMAERSWHAY-RNJNOEPSSA-N,"N2-((2S,3S,4E,6E,8S,9S)-3-((S)-2-((2S,3R)-3-((S)-2-amino-4-methylpentanamido)-3-carboxy-2-methylpropanamido)-5-guanidinopentanamido)-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)-N5-(3-(((R)-1-carboxyethyl)amino)-3-oxoprop-1-en-2-yl)-N5-methyl-D-glutamine",139583203,,10.1016/S0040-4039(00)61500-9,https://linkinghub.elsevier.com/retrieve/pii/S0040403900615009,"Isolation of linear peptides related to the hepatotoxins nodularin and microcystins;Tetrahedron Letters;34;49;;1993;journalArticle;10.1016/S0040-4039(00)61500-9;Choi, Byoung Wook; Namikoshi, Michio; Sun, Furong; Rinehart, Kenneth L.; Carmichael, Wayne W.; Kaup, Anne M.; Evans, William R.; Beasley, Val R.",Microcystis,sp.,n.a.,,Detected in field samples from Homer Lake (Illinois) (M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii)
CyanoMetDB_1798,MC-AR,,,Microcystin,C46H68N10O12,953.09,952.5018179,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C46H68N10O12/c1-24(22-25(2)35(68-9)23-31-14-11-10-12-15-31)17-18-32-26(3)38(58)54-34(44(64)65)19-20-36(57)56(8)30(7)42(62)51-28(5)40(60)50-29(6)41(61)55-37(45(66)67)27(4)39(59)53-33(43(63)52-32)16-13-21-49-46(47)48/h10-12,14-15,17-18,22,25-29,32-35,37H,7,13,16,19-21,23H2,1-6,8-9H3,(H,50,60)(H,51,62)(H,52,63)(H,53,59)(H,54,58)(H,55,61)(H,64,65)(H,66,67)(H4,47,48,49)/b18-17+,24-22+/t25-,26-,27-,28+,29-,32-,33-,34+,35-,37+/m0/s1",PIBNCDNEMSHYQS-QBBRADEDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,8,12,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101619975,,10.1021/jo00029a016,https://pubs.acs.org/doi/abs/10.1021/jo00029a016,"Identification of 12 hepatotoxins from a Homer Lake bloom of the cyanobacteria Microcystis aeruginosa, Microcystis viridis, and Microcystis wesenbergii: nine new microcystins;The Journal of Organic Chemistry;57;3;;1992;journalArticle;10.1021/jo00029a016;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Stotts, Richard R.; Dahlem, Andrew M.; Beasley, Val R.; Carmichael, Wayne W.; Evans, William R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria Microcystis aeruginosa (also contained Microcystis viridis and Microcystis wesenbergii),"Identified in field samples collected from Homer Lake (Illinois), consisted primarily of M. aeruginosa plus smaller quantities of M. uiridis and M. wesenbergii."
CyanoMetDB_1799,[D-Asp³]MC-RAba,[D-Asp³]MC-RAbu,,Microcystin,C46H68N10O12,953.09,952.5018179,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C46H68N10O12/c1-9-31-42(62)52-32(18-17-25(2)22-26(3)36(68-8)23-30-14-11-10-12-15-30)27(4)39(59)54-34(44(64)65)19-20-38(58)56(7)29(6)41(61)50-28(5)40(60)53-33(16-13-21-49-46(47)48)43(63)55-35(45(66)67)24-37(57)51-31/h10-12,14-15,17-18,22,26-28,31-36H,6,9,13,16,19-21,23-24H2,1-5,7-8H3,(H,50,61)(H,51,57)(H,52,62)(H,53,60)(H,54,59)(H,55,63)(H,64,65)(H,66,67)(H4,47,48,49)/b18-17+,25-22+/t26-,27-,28+,31-,32-,33-,34+,35+,36-/m0/s1",BIUWGLKOUISESS-LQCHMJEGSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-ethyl-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683815,,10.3390/md12115372,http://www.mdpi.com/1660-3397/12/11/5372,"High Levels of Structural Diversity Observed in Microcystins from Microcystis CAWBG11 and Characterization of Six New Microcystin Congeners;Marine Drugs;12;11;;2014;journalArticle;10.3390/md12115372;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Kaufononga, Sangata; Cary, Stephen; Hamilton, David",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1800,MC‐FR,,,Microcystin,C52H72N10O12,1029.19,1028.533118,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H72N10O12/c1-29(26-30(2)41(74-8)28-36-18-13-10-14-19-36)21-22-37-31(3)44(64)59-39(50(70)71)23-24-42(63)62(7)34(6)47(67)56-33(5)46(66)60-40(27-35-16-11-9-12-17-35)49(69)61-43(51(72)73)32(4)45(65)58-38(48(68)57-37)20-15-25-55-52(53)54/h9-14,16-19,21-22,26,30-33,37-41,43H,6,15,20,23-25,27-28H2,1-5,7-8H3,(H,56,67)(H,57,68)(H,58,65)(H,59,64)(H,60,66)(H,61,69)(H,70,71)(H,72,73)(H4,53,54,55)/b22-21+,29-26+/t30-,31-,32-,33+,37-,38-,39+,40-,41-,43+/m0/s1",NCIZAPYSXYPFOU-POWPIGGBSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101619974,,10.1016/S0021-9673(01)81837-9,https://linkinghub.elsevier.com/retrieve/pii/S0021967301818379,"Liquid chromatographic determination of the cyanoginosins, toxins produced by the cyanobacterium Microcystis aeruginosa;Journal of Chromatography A;408;;;1987;journalArticle;10.1016/S0021-9673(01)81837-9;Gathercole, P.S.; Thiel, P.G.",Microcystis,aeruginosa,[Microcystis aeruginosa]WR 70,,
CyanoMetDB_1801,MC-FAba,MC-FAbu ,,Microcystin,C50H67N7O12,958.11,957.4847709,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H67N7O12/c1-10-36-47(63)53-37(22-21-28(2)25-29(3)40(69-9)27-35-19-15-12-16-20-35)30(4)43(59)54-38(49(65)66)23-24-41(58)57(8)33(7)46(62)51-32(6)45(61)55-39(26-34-17-13-11-14-18-34)48(64)56-42(50(67)68)31(5)44(60)52-36/h11-22,25,29-32,36-40,42H,7,10,23-24,26-27H2,1-6,8-9H3,(H,51,62)(H,52,60)(H,53,63)(H,54,59)(H,55,61)(H,56,64)(H,65,66)(H,67,68)/b22-21+,28-25+/t29-,30-,31-,32+,36-,37-,38+,39-,40-,42+/m0/s1",ODVYEKWJJWPDCB-PMAKFENQSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-ethyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683816,,10.3390/md12115372,http://www.mdpi.com/1660-3397/12/11/5372,"High Levels of Structural Diversity Observed in Microcystins from Microcystis CAWBG11 and Characterization of Six New Microcystin Congeners;Marine Drugs;12;11;;2014;journalArticle;10.3390/md12115372;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Kaufononga, Sangata; Cary, Stephen; Hamilton, David",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1802,MC-RR,"Cyanoviridin-RR, Cyanogenosin-RR",,Microcystin,C49H75N13O12,1038.2,1037.565815,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C49H75N13O12/c1-26(24-27(2)37(74-8)25-32-14-10-9-11-15-32)18-19-33-28(3)40(64)60-36(46(70)71)20-21-38(63)62(7)31(6)43(67)56-30(5)42(66)59-35(17-13-23-55-49(52)53)45(69)61-39(47(72)73)29(4)41(65)58-34(44(68)57-33)16-12-22-54-48(50)51/h9-11,14-15,18-19,24,27-30,33-37,39H,6,12-13,16-17,20-23,25H2,1-5,7-8H3,(H,56,67)(H,57,68)(H,58,65)(H,59,66)(H,60,64)(H,61,69)(H,70,71)(H,72,73)(H4,50,51,54)(H4,52,53,55)/b19-18+,26-24+/t27-,28-,29-,30+,33-,34-,35-,36+,37-,39+/m0/s1",JIGDOBKZMULDHS-UUHBQKJESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6438357,,10.1016/S0040-4039(00)96600-0,https://linkinghub.elsevier.com/retrieve/pii/S0040403900966000,"Cyanoviridin RR, a toxin from the cyanobacterium (blue-green alga);Tetrahedron Letters;28;40;;1987;journalArticle;10.1016/S0040-4039(00)96600-0;Kusumi, Takenori; Ooi, Takashi; Watanabe, Makoto M.; Takahashi, Hiroshi; Kakisawa, Hiroshi",Microcystis,viridis,n.a.,,"Assessed using thiol derivatisation strategy. Detected in field samples collected from Homer Lake (Illinois), which consisted primarily of M. aeruginosa plus smaller quantities of M. viridis and M. wesenbergii."
CyanoMetDB_1803,[seco‐1/2]MC‐FR,L‐Phe‐D‐MeAsp(β)‐L‐Arg‐Adda‐D‐Glu(γ)‐Mdha‐D‐Ala‐OH,Microcystin RR,Microcystin,C52H74N10O13,1047.2,1046.543683,O=C(N(C)C(C(N[C@@H](C(O)=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N)CC2=CC=CC=C2)=O)=O)=O)=O,"InChI=1S/C52H74N10O13/c1-29(26-30(2)41(75-8)28-36-18-13-10-14-19-36)21-22-38(31(3)44(64)60-40(50(71)72)23-24-42(63)62(7)34(6)46(66)57-33(5)49(69)70)58-48(68)39(20-15-25-56-52(54)55)59-45(65)32(4)43(51(73)74)61-47(67)37(53)27-35-16-11-9-12-17-35/h9-14,16-19,21-22,26,30-33,37-41,43H,6,15,20,23-25,27-28,53H2,1-5,7-8H3,(H,57,66)(H,58,68)(H,59,65)(H,60,64)(H,61,67)(H,69,70)(H,71,72)(H,73,74)(H4,54,55,56)/b22-21+,29-26+/t30-,31-,32-,33+,37-,38-,39-,40+,41-,43+/m0/s1",NGLPKMLVTYMODN-UUUMXHOZSA-N,"N2-((2S,3S,4E,6E,8S,9S)-3-((S)-2-((2S,3R)-3-((S)-2-amino-3-phenylpropanamido)-3-carboxy-2-methylpropanamido)-5-guanidinopentanamido)-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)-N5-(3-(((R)-1-carboxyethyl)amino)-3-oxoprop-1-en-2-yl)-N5-methyl-D-glutamine",155802218,DTXSID40880085,10.1016/S0040-4039(00)61500-9,https://linkinghub.elsevier.com/retrieve/pii/S0040403900615009,"Isolation of linear peptides related to the hepatotoxins nodularin and microcystins;Tetrahedron Letters;34;49;;1993;journalArticle;10.1016/S0040-4039(00)61500-9;Choi, Byoung Wook; Namikoshi, Michio; Sun, Furong; Rinehart, Kenneth L.; Carmichael, Wayne W.; Kaup, Anne M.; Evans, William R.; Beasley, Val R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii,Compound 5 (Choi 1993) and 14 (Namikoshi 1995) in cited refs. Detected in field samples from Homer Lake (Illinois) (M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii)
CyanoMetDB_1804,[D-Asp³]MC-RA,,,Microcystin,C45H66N10O12,939.07,938.4861679,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C45H66N10O12/c1-24(21-25(2)35(67-8)22-30-13-10-9-11-14-30)16-17-31-26(3)38(58)53-33(43(63)64)18-19-37(57)55(7)29(6)41(61)50-28(5)40(60)52-32(15-12-20-48-45(46)47)42(62)54-34(44(65)66)23-36(56)49-27(4)39(59)51-31/h9-11,13-14,16-17,21,25-28,31-35H,6,12,15,18-20,22-23H2,1-5,7-8H3,(H,49,56)(H,50,61)(H,51,59)(H,52,60)(H,53,58)(H,54,62)(H,63,64)(H,65,66)(H4,46,47,48)/b17-16+,24-21+/t25-,26-,27-,28+,31-,32-,33+,34+,35-/m0/s1",FXSKUDKICQOZGL-JEPMYZTKSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,15,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684718,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Hapalosiphon; Microcystis,[Hapalosiphon]hibernicus; [Microcystis]sp.,[Hapalosiphon hibernicus]BZ-3-1;[Microcystis sp.]CAWBG11,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1805,MC‐AHar,,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O12/c1-25(23-26(2)36(69-9)24-32-15-11-10-12-16-32)18-19-33-27(3)39(59)55-35(45(65)66)20-21-37(58)57(8)31(7)43(63)52-29(5)41(61)51-30(6)42(62)56-38(46(67)68)28(4)40(60)54-34(44(64)53-33)17-13-14-22-50-47(48)49/h10-12,15-16,18-19,23,26-30,33-36,38H,7,13-14,17,20-22,24H2,1-6,8-9H3,(H,51,61)(H,52,63)(H,53,64)(H,54,60)(H,55,59)(H,56,62)(H,65,66)(H,67,68)(H4,48,49,50)/b19-18+,25-23+/t26-,27-,28-,29+,30-,33-,34-,35+,36-,38+/m0/s1",BMWJSAZEZUBFNG-HQXMUDDSSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(4-guanidinobutyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,8,12,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801660,,10.1016/j.hal.2008.08.014,https://linkinghub.elsevier.com/retrieve/pii/S1568988308001169,"Stability of toxigenic Microcystis blooms;Harmful Algae;8;3;;2009;journalArticle;10.1016/j.hal.2008.08.014;Prakash, Satya; Lawton, Linda A.; Edwards, Christine",n.a.,n.a.,n.a.,"field samples, cultures of cyanobacteria (Microcystis ?) from samples of five eutrophic ponds; Lakshmikund, Karmadeshwar, Adityanagar, Durgakund and Sankuldhara in Varanasi, Uttar Pradesh, India (25°20′N, 83°01′E) ","Tentative assignment in bloom samples collected from five eutrophic ponds (Lakshmikund, Karmadeshwar, Adityanagar, Durgakund and Sankuldhara in Varanasi, Uttar Pradesh - India). Stereochemistry inferred from other MC congeners."
CyanoMetDB_1806,"[D‐Asp³,DMAdda5]MC‐LR",,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C47H70N10O12/c1-25(2)21-35-44(65)56-36(46(68)69)24-38(59)52-33(15-12-20-50-47(48)49)43(64)53-32(17-16-26(3)22-27(4)37(58)23-31-13-10-9-11-14-31)28(5)40(61)54-34(45(66)67)18-19-39(60)57(8)30(7)42(63)51-29(6)41(62)55-35/h9-11,13-14,16-17,22,25,27-29,32-37,58H,7,12,15,18-21,23-24H2,1-6,8H3,(H,51,63)(H,52,59)(H,53,64)(H,54,61)(H,55,62)(H,56,65)(H,66,67)(H,68,69)(H4,48,49,50)/b17-16+,26-22+/t27-,28-,29+,32-,33-,34+,35-,36+,37-/m0/s1",FYRAXCGEXQMBHA-RHFXSWBISA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-isobutyl-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684737,,10.1094/MPMI-22-6-0695,http://apsjournals.apsnet.org/doi/10.1094/MPMI-22-6-0695,"Microcystin Production in the Tripartite Cyanolichen Peltigera leucophlebia;Molecular Plant-Microbe Interactions;22;6;;2009;journalArticle;10.1094/MPMI-22-6-0695;Kaasalainen, Ulla; Jokela, Jouni; Fewer, David P.; Sivonen, Kaarina; Rikkinen, Jouko",Nostoc,sp.,[Nostoc sp.]UK18,,Stereochemistry assumed based on other MC congeners. Also detected in Peltigera leucophlebia (lichen species)
CyanoMetDB_1807,"[Asp³,DMAdda5,Dhb7]MC‐LR",,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C47H70N10O12/c1-8-31-42(63)51-29(7)41(62)56-35(21-25(2)3)44(65)57-36(46(68)69)24-39(60)53-33(15-12-20-50-47(48)49)43(64)54-32(28(6)40(61)55-34(45(66)67)18-19-38(59)52-31)17-16-26(4)22-27(5)37(58)23-30-13-10-9-11-14-30/h8-11,13-14,16-17,22,25,27-29,32-37,58H,12,15,18-21,23-24H2,1-7H3,(H,51,63)(H,52,59)(H,53,60)(H,54,64)(H,55,61)(H,56,62)(H,57,65)(H,66,67)(H,68,69)(H4,48,49,50)/b17-16+,26-22+,31-8?/t27-,28-,29+,32-,33-,34+,35-,36+,37-/m0/s1",UYJLVJJFDLREAV-OHXBTAIVSA-N,"(E)-15-(3-((diaminomethylene)amino)propyl)-2-ethylidene-18-((1E,3E)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-isobutyl-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",,,10.1021/es305202p,https://pubs.acs.org/doi/10.1021/es305202p,"LC-MS Analysis with Thiol Derivatization to Differentiate [Dhb 7 ]- from [Mdha 7 ]-Microcystins: Analysis of Cyanobacterial Blooms, Planktothrix Cultures and European Crayfish from Lake Steinsfjorden, Norway;Environmental Science & Technology;47;9;;2013;journalArticle;10.1021/es305202p;Miles, Christopher O.; Sandvik, Morten; Haande, Sigrid; Nonga, Hezron; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample: Planktothrix cultures from Lake Steinsfjorden, Norway","Tentative annotation. Stereochemistry assumed based on other microcystin structures. Detected in a concentrated phytoplankton sample derived from a net sample (25 μm mesh) taken from L. Steinsfjorden, Norway - Planktothrix agardhii was reported as major species in epilimnion (0-7 m), but was only moderately abundant in the metalimnion (8-14 m)."
CyanoMetDB_1808,"[Gly1,D-Asp3,Dhb7]MC-LR",,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)CCCNC(=N)N)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O12/c1-8-31-42(62)51-25-40(60)54-35(21-26(2)3)44(64)57-36(46(67)68)24-39(59)53-33(15-12-20-50-47(48)49)43(63)55-32(29(6)41(61)56-34(45(65)66)18-19-38(58)52-31)17-16-27(4)22-28(5)37(69-7)23-30-13-10-9-11-14-30/h8-11,13-14,16-17,22,26,28-29,32-37H,12,15,18-21,23-25H2,1-7H3,(H,51,62)(H,52,58)(H,53,59)(H,54,60)(H,55,63)(H,56,61)(H,57,64)(H,65,66)(H,67,68)(H4,48,49,50)/b17-16+,27-22+,31-8?/t28-,29-,32-,33-,34+,35-,36+,37-/m0/s1",JWJFTKPARURZJD-GNURSVSOSA-N,"(8S,11R,15S,18S,19S,22R,Z)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-2-ethylidene-15-(3-guanidinopropyl)-8-isobutyl-19-methyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)",
CyanoMetDB_1809,[D-Asp3]MC-HarAba,[D-Asp3]MC-HarAbu,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)C[C@@H](NC(=O)[C@H](CCCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O12/c1-9-32-43(63)53-33(19-18-26(2)23-27(3)37(69-8)24-31-15-11-10-12-16-31)28(4)40(60)55-35(45(65)66)20-21-39(59)57(7)30(6)42(62)51-29(5)41(61)54-34(17-13-14-22-50-47(48)49)44(64)56-36(46(67)68)25-38(58)52-32/h10-12,15-16,18-19,23,27-29,32-37H,6,9,13-14,17,20-22,24-25H2,1-5,7-8H3,(H,51,62)(H,52,58)(H,53,63)(H,54,61)(H,55,60)(H,56,64)(H,65,66)(H,67,68)(H4,48,49,50)/b19-18+,26-23+/t27-,28-,29+,32-,33-,34-,35+,36+,37-/m0/s1",QGPGQAYAXHVIEF-VCTGLOHFSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-ethyl-8-(4-guanidinobutyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683861,,10.1016/j.envpol.2016.06.055,https://linkinghub.elsevier.com/retrieve/pii/S0269749116305437,"High diversity of microcystins in a Microcystis bloom from an Algerian lake;Environmental Pollution;216;;;2016;journalArticle;10.1016/j.envpol.2016.06.055;Bouhaddada, Ratiba; Nélieu, Sylvie; Nasri, Hichem; Delarue, Ghislaine; Bouaïcha, Noureddine",n.a.,n.a.,n.a.,"field sample Lake des Oiseaux (36°42′N 008°07′E), north-eastern Algeria","Position 7 moiety is assumed to be Mdha (MS-only analyses, hence unable to differentiate Mdha from Dhb). Bloom samples from Lake des Oiseaux located in north-eastern Algeria."
CyanoMetDB_1810,"[Gly1,D-Asp3]MC-LR",,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O12/c1-26(2)21-35-44(64)56-36(46(67)68)24-38(58)52-33(15-12-20-50-47(48)49)43(63)54-32(17-16-27(3)22-28(4)37(69-8)23-31-13-10-9-11-14-31)29(5)41(61)55-34(45(65)66)18-19-40(60)57(7)30(6)42(62)51-25-39(59)53-35/h9-11,13-14,16-17,22,26,28-29,32-37H,6,12,15,18-21,23-25H2,1-5,7-8H3,(H,51,62)(H,52,58)(H,53,59)(H,54,63)(H,55,61)(H,56,64)(H,65,66)(H,67,68)(H4,48,49,50)/b17-16+,27-22+/t28-,29-,32-,33-,34+,35-,36+,37-/m0/s1",UHGAEMBYJRDQQV-JQHMHAMLSA-N,"(8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683832,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",n.a.,n.a.,n.a.,"field samples, from various benthic mats",From Antarctica. Compound MC-1 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1811,[D-Asp³]MC-WA,,,Microcystin,C50H64N8O12,969.09,968.4643698,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)C[C@@H](NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H64N8O12/c1-27(22-28(2)41(70-8)23-33-14-10-9-11-15-33)18-19-36-29(3)44(61)55-38(49(66)67)20-21-43(60)58(7)32(6)47(64)53-31(5)46(63)56-39(24-34-26-51-37-17-13-12-16-35(34)37)48(65)57-40(50(68)69)25-42(59)52-30(4)45(62)54-36/h9-19,22,26,28-31,36,38-41,51H,6,20-21,23-25H2,1-5,7-8H3,(H,52,59)(H,53,64)(H,54,62)(H,55,61)(H,56,63)(H,57,65)(H,66,67)(H,68,69)/b19-18+,27-22+/t28-,29-,30-,31+,36-,38+,39-,40+,41-/m0/s1",YHSLBZZOBKSXCV-RQZXCYPXSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-(indolin-3-ylmethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,15,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683817,,10.3390/md12115372,http://www.mdpi.com/1660-3397/12/11/5372,"High Levels of Structural Diversity Observed in Microcystins from Microcystis CAWBG11 and Characterization of Six New Microcystin Congeners;Marine Drugs;12;11;;2014;journalArticle;10.3390/md12115372;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Kaufononga, Sangata; Cary, Stephen; Hamilton, David",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1812,[D-Asp3]MC-EE,,,Microcystin,C46H63N7O16,970.03,969.433129,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)O)NC(=O)C[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C46H63N7O16/c1-24(21-25(2)35(69-7)22-29-11-9-8-10-12-29)13-14-30-26(3)40(60)51-33(45(65)66)15-18-37(55)53(6)28(5)42(62)47-27(4)41(61)50-32(17-20-39(58)59)44(64)52-34(46(67)68)23-36(54)48-31(43(63)49-30)16-19-38(56)57/h8-14,21,25-27,30-35H,5,15-20,22-23H2,1-4,6-7H3,(H,47,62)(H,48,54)(H,49,63)(H,50,61)(H,51,60)(H,52,64)(H,56,57)(H,58,59)(H,65,66)(H,67,68)/b14-13+,24-21+/t25-,26-,27+,30-,31-,32-,33+,34+,35-/m0/s1",RRMMYXRMUVPVRF-NSKJAONYSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8,15-bis(2-carboxyethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683811,,10.3390/md17110643,https://www.mdpi.com/1660-3397/17/11/643,"Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling;Marine Drugs;17;11;;2019;journalArticle;10.3390/md17110643;Mallia, Vittoria; Uhlig, Silvio; Rafuse, Cheryl; Meija, Juris; Miles, Christopher O.",Planktothrix ,prolifica ,NIVA-CYA 544,,
CyanoMetDB_1813,"[D-Asp3,Dha7]MC-EE(OMe)",,,Microcystin,C46H63N7O16,970.03,969.4331293,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)OC)NC(=O)C[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C46H63N7O16/c1-24(21-25(2)35(68-6)22-29-11-9-8-10-12-29)13-14-30-26(3)40(59)52-33(45(64)65)15-18-36(54)47-27(4)41(60)48-28(5)42(61)51-32(16-19-38(56)57)44(63)53-34(46(66)67)23-37(55)49-31(43(62)50-30)17-20-39(58)69-7/h8-14,21,25-26,28,30-35H,4,15-20,22-23H2,1-3,5-7H3,(H,47,54)(H,48,60)(H,49,55)(H,50,62)(H,51,61)(H,52,59)(H,53,63)(H,56,57)(H,64,65)(H,66,67)/b14-13+,24-21+/t25-,26-,28+,30-,31-,32-,33+,34+,35-/m0/s1",CKZSVUYCUATPFE-ZEHFFRFMSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-(2-carboxyethyl)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-15-(3-methoxy-3-oxopropyl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683842,,10.1021/tx970120t,https://pubs.acs.org/doi/10.1021/tx970120t,"Seven New Microcystins Possessing Two Glutamic Acid Units Isolated from Anabaena sp. Strain 186;Chemical Research in Toxicology;11;2;;1998;journalArticle;10.1021/tx970120t;Namikoshi, Michio; Yuan, Moucun; Sivonen, Kaarina; Carmichael, Wayne W.; Rinehart, Kenneth L.; Rouhiainen, Leo; Sun, Furong; Brittain, Scott; Otsuki, Akira",Anabaena,n.a.,[Anabaena sp.]186,,Cited reference reports an insufficient amount was recovered to enable chirality assessment of amino acid moieties. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1814,MC-LM,,,Microcystin,C48H71N7O12S,970.18,969.4881417,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCSC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H71N7O12S/c1-26(2)23-37-46(62)54-40(48(65)66)30(6)42(58)51-35(21-22-68-11)45(61)50-34(18-17-27(3)24-28(4)38(67-10)25-33-15-13-12-14-16-33)29(5)41(57)52-36(47(63)64)19-20-39(56)55(9)32(8)44(60)49-31(7)43(59)53-37/h12-18,24,26,28-31,34-38,40H,8,19-23,25H2,1-7,9-11H3,(H,49,60)(H,50,61)(H,51,58)(H,52,57)(H,53,59)(H,54,62)(H,63,64)(H,65,66)/b18-17+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",KZWVAQXKWCQPOF-XREXUNHVSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-15-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684695,,10.1016/0041-0101(93)90338-J,https://linkinghub.elsevier.com/retrieve/pii/004101019390338J,"Identification and characterization of hydrophobic microcystins in Canadian freshwater cyanobacteria;Toxicon;31;12;;1993;journalArticle;10.1016/0041-0101(93)90338-J;Craig, Marcia; McCready, Tara L.; Luu, Hue A.; Smillie, Mark A.; Dubord, Pierre; Holmes, Charles F.B.",Microcystis,aeruginosa,n.a.,,"Putative annotation only. Structure determined using a combination of bio-assay guided LC fractionation and amino acid analysis. No complementary analytical techniques (e.g. MS/NMR) applied. Source: cyanobacteria (containing predominantly Microcystis aeruginosa) was collected from a bloom present on Little Beaver Lake (Alberta, Canada). "
CyanoMetDB_1815,MC-VF,,,Microcystin,C51H69N7O12,972.13,971.500421,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H69N7O12/c1-28(2)42-49(65)57-43(51(68)69)32(6)45(61)55-39(26-35-17-13-11-14-18-35)48(64)53-37(22-21-29(3)25-30(4)40(70-10)27-36-19-15-12-16-20-36)31(5)44(60)54-38(50(66)67)23-24-41(59)58(9)34(8)47(63)52-33(7)46(62)56-42/h11-22,25,28,30-33,37-40,42-43H,8,23-24,26-27H2,1-7,9-10H3,(H,52,63)(H,53,64)(H,54,60)(H,55,61)(H,56,62)(H,57,65)(H,66,67)(H,68,69)/b22-21+,29-25+/t30-,31-,32-,33+,37-,38+,39-,40-,42-,43+/m0/s1",PBXDBYLJLRGSMP-LKCZJABDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-benzyl-8-isopropyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684697,,10.1016/0021-9673(95)00438-S,https://linkinghub.elsevier.com/retrieve/pii/002196739500438S,"Mass spectral analyses of microcystins from toxic cyanobacteria using on-line chromatographic and electrophoretic separations;Journal of Chromatography A;712;1;;1995;journalArticle;10.1016/0021-9673(95)00438-S;Bateman, K.P; Thibault, P; Douglas, D.J; White, R.L",Microcystis,aeruginosa,[Microcystis aeruginosa]PCC7820,,Characterisation is based on MS/MS and therefore stereochemistries are assumed. 15N labeling used to support annotation of fragment ions.
CyanoMetDB_1816,MC-RAba,MC‐RAbu,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O12/c1-10-32-43(63)53-33(19-18-25(2)23-26(3)36(69-9)24-31-15-12-11-13-16-31)27(4)39(59)55-35(45(65)66)20-21-37(58)57(8)30(7)42(62)51-29(6)41(61)54-34(17-14-22-50-47(48)49)44(64)56-38(46(67)68)28(5)40(60)52-32/h11-13,15-16,18-19,23,26-29,32-36,38H,7,10,14,17,20-22,24H2,1-6,8-9H3,(H,51,62)(H,52,60)(H,53,63)(H,54,61)(H,55,59)(H,56,64)(H,65,66)(H,67,68)(H4,48,49,50)/b19-18+,25-23+/t26-,27-,28-,29+,32-,33-,34-,35+,36-,38+/m0/s1",WXXHHUKDBIZLGN-WGWRYDTPSA-N,"8-(3-((diaminomethylene)amino)propyl)-15-ethyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684761,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,sp.,n.a.,,
CyanoMetDB_1817,MC-YAba,MC‐YAbu,,Microcystin,C50H67N7O13,974.11,973.4796855,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H67N7O13/c1-10-36-47(64)53-37(21-16-27(2)24-28(3)40(70-9)26-33-14-12-11-13-15-33)29(4)43(60)54-38(49(66)67)22-23-41(59)57(8)32(7)46(63)51-31(6)45(62)55-39(25-34-17-19-35(58)20-18-34)48(65)56-42(50(68)69)30(5)44(61)52-36/h11-21,24,28-31,36-40,42,58H,7,10,22-23,25-26H2,1-6,8-9H3,(H,51,63)(H,52,61)(H,53,64)(H,54,60)(H,55,62)(H,56,65)(H,66,67)(H,68,69)/b21-16+,27-24+/t28-,29-,30-,31+,36-,37-,38+,39-,40-,42+/m0/s1",YKLLLBNAMZGEMS-BIOYDOLKSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-ethyl-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684754,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry assumed based on other MC congeners. Annotation based on MS analysis of native and thiol-derivatised compound using precursor ion scanning and data-dependent MS/MS approaches, plus similarity of structure to a 1D and 2D-NMR-analysed MC-RY compound."
CyanoMetDB_1818,"[D-Asp3,Dha7]MC‐LY",,,Microcystin,C50H67N7O13,974.11,973.4796855,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H67N7O13/c1-27(2)22-38-47(64)57-40(50(68)69)26-43(60)53-39(24-34-15-17-35(58)18-16-34)48(65)54-36(19-14-28(3)23-29(4)41(70-8)25-33-12-10-9-11-13-33)30(5)44(61)55-37(49(66)67)20-21-42(59)51-31(6)45(62)52-32(7)46(63)56-38/h9-19,23,27,29-30,32,36-41,58H,6,20-22,24-26H2,1-5,7-8H3,(H,51,59)(H,52,62)(H,53,60)(H,54,65)(H,55,61)(H,56,63)(H,57,64)(H,66,67)(H,68,69)/b19-14+,28-23+/t29-,30-,32+,36-,37+,38-,39-,40+,41-/m0/s1",XUJFVYZYMHMSRZ-CANMJJLKSA-N,"15-(4-hydroxybenzyl)-8-isobutyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802427,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,[Microcystis aeruginosa]CYA548,,Stereochemistry assumed based on other MC congeners (LC-MS/MS and HRMS analyses unable to confirm this)
CyanoMetDB_1819,"[Gly1,D-Asp3]MC-LHar",,,Microcystin,C48H72N10O12,981.15,980.5331178,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12/c1-27(2)22-36-45(65)57-37(47(68)69)25-39(59)53-34(16-12-13-21-51-48(49)50)44(64)55-33(18-17-28(3)23-29(4)38(70-8)24-32-14-10-9-11-15-32)30(5)42(62)56-35(46(66)67)19-20-41(61)58(7)31(6)43(63)52-26-40(60)54-36/h9-11,14-15,17-18,23,27,29-30,33-38H,6,12-13,16,19-22,24-26H2,1-5,7-8H3,(H,52,63)(H,53,59)(H,54,60)(H,55,64)(H,56,62)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,28-23+/t29-,30-,33-,34-,35+,36-,37+,38-/m0/s1",JSPVTQVNXUVMTI-GYSRTOPMSA-N,"(8S,11R,15S,18S,19S,22R)-15-(4-guanidinobutyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683833,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",n.a.,n.a.,n.a.,"field samples, from various benthic mats",From Antarctica. Compound MC-3 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1820,"[D-Asp3,(E)-Dhb7]MC-LR",,,Microcystin,C48H72N10O12,981.15,980.5331181,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C\C)/NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12/c1-9-32-43(63)52-30(7)42(62)57-36(22-26(2)3)45(65)58-37(47(68)69)25-40(60)54-34(16-13-21-51-48(49)50)44(64)55-33(29(6)41(61)56-35(46(66)67)19-20-39(59)53-32)18-17-27(4)23-28(5)38(70-8)24-31-14-11-10-12-15-31/h9-12,14-15,17-18,23,26,28-30,33-38H,13,16,19-22,24-25H2,1-8H3,(H,52,63)(H,53,59)(H,54,60)(H,55,64)(H,56,61)(H,57,62)(H,58,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,27-23+,32-9+/t28-,29-,30+,33-,34-,35+,36-,37+,38-/m0/s1",VDTOBYMILGRBLM-ZUCGMWCSSA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",21637043,,10.1016/S0040-4020(97)10291-5,https://linkinghub.elsevier.com/retrieve/pii/S0040402097102915,"Two new (E)-2-amino-2-butenoic acid (Dhb)-containing microcystins isolated from Oscillatoria agardhii;Tetrahedron;54;43924;;1998;journalArticle;10.1016/S0040-4020(97)10291-5;Sano, Tomoharu; Kaya, Kunimitsu",Oscillatoria/Planktothrix,agardhii,[Oscillatoria agardhii]CCAP 1459/14,,
CyanoMetDB_1821,[D‐Asp3]MC‐HilR,[D‐Asp3]MC‐HilR/HleR,,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](C[C@@H](C)CC)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O12/c1-10-27(2)24-37-46(66)58-38(48(69)70)26-40(60)54-35(17-14-22-52-49(50)51)45(65)55-34(19-18-28(3)23-29(4)39(71-9)25-33-15-12-11-13-16-33)30(5)42(62)56-36(47(67)68)20-21-41(61)59(8)32(7)44(64)53-31(6)43(63)57-37/h11-13,15-16,18-19,23,27,29-31,34-39H,7,10,14,17,20-22,24-26H2,1-6,8-9H3,(H,53,64)(H,54,60)(H,55,65)(H,56,62)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,28-23+/t27-,29-,30-,31+,34-,35-,36+,37-,38+,39-/m0/s1",XRRFSPPWGAFDRM-UONDCLTESA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684703,,10.1007/s00203-004-0711-3,http://link.springer.com/10.1007/s00203-004-0711-3,"Diversity of coexisting Planktothrix (Cyanobacteria) chemotypes deduced by mass spectral analysis of microystins and other oligopeptides;Archives of Microbiology;182;4;;2004;journalArticle;10.1007/s00203-004-0711-3;Welker, Martin; Christiansen, Guntram; von Döhren, Hans",Planktothrix; Dolichospermum/Anabaena,[Planktothrix]sp.; [Dolichospermum]sp.,[Planktothrix sp.]Max06;[Dolichospermum sp.]90,,"Of the two options, Hle or Hil, Hil is commonly observed in MCs. Stereochemistry assumed based on other MC congeners. "
CyanoMetDB_1822,MC‐HphR,,,Microcystin,C53H74N10O12,1043.21,1042.548768,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C53H74N10O12/c1-30(28-31(2)42(75-8)29-37-18-13-10-14-19-37)21-23-38-32(3)45(65)61-41(51(71)72)25-26-43(64)63(7)35(6)48(68)57-34(5)47(67)60-40(24-22-36-16-11-9-12-17-36)50(70)62-44(52(73)74)33(4)46(66)59-39(49(69)58-38)20-15-27-56-53(54)55/h9-14,16-19,21,23,28,31-34,38-42,44H,6,15,20,22,24-27,29H2,1-5,7-8H3,(H,57,68)(H,58,69)(H,59,66)(H,60,67)(H,61,65)(H,62,70)(H,71,72)(H,73,74)(H4,54,55,56)/b23-21+,30-28+/t31-,32-,33-,34+,38-,39-,40-,41+,42-,44+/m0/s1",JBHWKMHTUYRELH-CKWYSMNFSA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684779,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,MS2 available in the article
CyanoMetDB_1823,MC-LR,,,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",ZYZCGGRZINLQBL-GWRQVWKTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-isobutyl-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",445434,,10.1039/p19850002747,http://xlink.rsc.org/?DOI=p19850002747,"Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa;Journal of the Chemical Society, Perkin Transactions 1;;;;1985;journalArticle;10.1039/p19850002747;Botes, Dawie P.; Wessels, Philippus L.; Kruger, Hel�ne; Runnegar, Maria T. C.; Santikarn, Sitthivet; Smith, Richard J.; Barna, Jennifer C. J.; Williams, Dudley H.",Microcystis,aeruginosa,n.a.,,"Botes et al. originally reported the possible occurrence of MC-YA, but detection was based only on 1H NMR (insufficient quantities for FAB-MS). No molecular formula proposed."
CyanoMetDB_1824,"[D-Asp3,(Z)-Dhb7]MC-LR",,,Microcystin,C48H72N10O12,981.15,980.5331181,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12/c1-9-32-43(63)52-30(7)42(62)57-36(22-26(2)3)45(65)58-37(47(68)69)25-40(60)54-34(16-13-21-51-48(49)50)44(64)55-33(29(6)41(61)56-35(46(66)67)19-20-39(59)53-32)18-17-27(4)23-28(5)38(70-8)24-31-14-11-10-12-15-31/h9-12,14-15,17-18,23,26,28-30,33-38H,13,16,19-22,24-25H2,1-8H3,(H,52,63)(H,53,59)(H,54,60)(H,55,64)(H,56,61)(H,57,62)(H,58,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,27-23+,32-9-/t28-,29-,30+,33-,34-,35+,36-,37+,38-/m0/s1",VDTOBYMILGRBLM-LIEPGKHHSA-N,"(5R,8S,11R,15S,18S,19S,22R,Z)-2-ethylidene-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",21635774,,10.1021/np980047m,https://pubs.acs.org/doi/10.1021/np980047m,"Two ( Z )-Dehydrobutyrine-Containing Microcystins from a Hepatotoxic Bloom of Oscillatoria a gardhii from Soulseat Loch, Scotland;Journal of Natural Products;61;6;;1998;journalArticle;10.1021/np980047m;Sano, Tomoharu; Beattie, Kenneth A.; Codd, Geoffrey A.; Kaya, Kunimitsu",Oscillatoria/Planktothrix,agardhii,n.a.,,"Cyanobacterial cells were collected from an extensive shoreline scum at Soulseat Loch, southwest Scotland (O. agardhii)"
CyanoMetDB_1825,"[Gly1,D-Asp3,(E/Z)-Dhb7]MC-LHar",,,Microcystin,C48H72N10O12,981.15,980.5331181,O=C(NC(C(NCC1=O)=O)=CC)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C48H72N10O12/c1-8-32-43(63)52-26-41(61)55-36(22-27(2)3)45(65)58-37(47(68)69)25-40(60)54-34(16-12-13-21-51-48(49)50)44(64)56-33(30(6)42(62)57-35(46(66)67)19-20-39(59)53-32)18-17-28(4)23-29(5)38(70-7)24-31-14-10-9-11-15-31/h8-11,14-15,17-18,23,27,29-30,33-38H,12-13,16,19-22,24-26H2,1-7H3,(H,52,63)(H,53,59)(H,54,60)(H,55,61)(H,56,64)(H,57,62)(H,58,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,28-23+,32-8?/t29-,30-,33-,34-,35+,36-,37+,38-/m0/s1",HPNBXNCKNWSRPX-RYDRMDOGSA-N,"(8S,11R,15S,18S,19S,22R)-2-ethylidene-15-(4-guanidinobutyl)-3,6,9,13,16,20,25-heptahydroxy-8-isobutyl-18-((1E,3Z,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-19-methyl-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20,25-heptaene-11,22-dicarboxylic acid",155802093,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)",Stereochemistry partially defined by advanced Marfey amino acid analysis
CyanoMetDB_1826,MC‐RApa,,,Microcystin,C48H72N10O12,981.15,980.5331181,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)C(C)C)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12/c1-25(2)38-45(65)53-33(19-18-26(3)23-27(4)36(70-10)24-32-15-12-11-13-16-32)28(5)40(60)55-35(46(66)67)20-21-37(59)58(9)31(8)43(63)52-30(7)42(62)54-34(17-14-22-51-48(49)50)44(64)57-39(47(68)69)29(6)41(61)56-38/h11-13,15-16,18-19,23,25,27-30,33-36,38-39H,8,14,17,20-22,24H2,1-7,9-10H3,(H,52,63)(H,53,65)(H,54,62)(H,55,60)(H,56,61)(H,57,64)(H,66,67)(H,68,69)(H4,49,50,51)/b19-18+,26-23+/t27-,28-,29-,30+,33-,34-,35+,36-,38-,39+/m0/s1",JTVRQNBTJXUUHH-JKJOTVENSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(3-guanidinopropyl)-15-isopropyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684755,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry assumed based on other MC congeners. Building block 4 is given as aminopropionic acid, which is the core of the structure at this position. The full structure at position 4 is inferred to be valine. Annotation based on MS analysis of native and thiol-derivatised compound using precursor ion scanning and data-dependent MS/MS approaches, plus similarity of structure to a 1D and 2D-NMR-analysed MC-RY compound."
CyanoMetDB_1827,MC‐VR,,,Microcystin,C48H72N10O12,981.15,980.5331181,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12/c1-25(2)38-45(65)57-39(47(68)69)29(6)41(61)54-34(17-14-22-51-48(49)50)44(64)53-33(19-18-26(3)23-27(4)36(70-10)24-32-15-12-11-13-16-32)28(5)40(60)55-35(46(66)67)20-21-37(59)58(9)31(8)43(63)52-30(7)42(62)56-38/h11-13,15-16,18-19,23,25,27-30,33-36,38-39H,8,14,17,20-22,24H2,1-7,9-10H3,(H,52,63)(H,53,64)(H,54,61)(H,55,60)(H,56,62)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b19-18+,26-23+/t27-,28-,29-,30+,33-,34-,35+,36-,38-,39+/m0/s1",ZIPMGCZUAQPWCC-JKJOTVENSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isopropyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",15160482,,10.5697/oc.52-1.127,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Morphological, genetic, chemical and ecophysiological characterisation of two Microcystis aeruginosa isolates from the Vistula Lagoon, southern Baltic;OCEANOLOGIA;52;1;;2010;journalArticle;10.5697/oc.52-1.127;Mazur-Marzec, Hanna; Forycka, Karolina; Kobos, Justyna; Pliński, Marcin; Browarczyk-Matusiak, Grażyna",Microcystis,aeruginosa,[Microcystis aeruginosa]MK10.10,,"MS used for structural elucidation, therefore stereochemistry is assumed."
CyanoMetDB_1828,MC-WA,,,Microcystin,C51H66N8O12,983.12,982.4800199,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H66N8O12/c1-27(23-28(2)41(71-9)24-34-15-11-10-12-16-34)19-20-37-29(3)44(61)56-39(50(67)68)21-22-42(60)59(8)33(7)48(65)54-32(6)47(64)57-40(25-35-26-52-38-18-14-13-17-36(35)38)49(66)58-43(51(69)70)30(4)45(62)53-31(5)46(63)55-37/h10-20,23,26,28-32,37,39-41,43,52H,7,21-22,24-25H2,1-6,8-9H3,(H,53,62)(H,54,65)(H,55,63)(H,56,61)(H,57,64)(H,58,66)(H,67,68)(H,69,70)/b20-19+,27-23+/t28-,29-,30-,31-,32+,37-,39+,40-,41-,43+/m0/s1",JRDNHFSGYCALIM-JMEOANFWSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(indolin-3-ylmethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802136,,10.1016/j.phytol.2013.07.011,https://linkinghub.elsevier.com/retrieve/pii/S1874390013001328,"Isolation and structure determination of two new hydrophobic microcystins from Microcystis sp. (CAWBG11);Phytochemistry Letters;6;4;;2013;journalArticle;10.1016/j.phytol.2013.07.011;Puddick, Jonathan; Prinsep, Michèle R.; Wood, Susanna A.; Cary, S. Craig; Hamilton, David P.; Wilkins, Alistair L.",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Absolute stereochemistry defined via Marfey's amino acid analysis
CyanoMetDB_1829,MC-AW,,,Microcystin,C51H66N8O12,983.12,982.4800199,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H66N8O12/c1-27(23-28(2)41(71-9)24-34-15-11-10-12-16-34)19-20-37-29(3)44(61)56-39(50(67)68)21-22-42(60)59(8)33(7)48(65)54-31(5)46(63)53-32(6)47(64)58-43(51(69)70)30(4)45(62)57-40(49(66)55-37)25-35-26-52-38-18-14-13-17-36(35)38/h10-20,23,26,28-32,37,39-41,43,52H,7,21-22,24-25H2,1-6,8-9H3,(H,53,63)(H,54,65)(H,55,66)(H,56,61)(H,57,62)(H,58,64)(H,67,68)(H,69,70)/b20-19+,27-23+/t28-,29-,30-,31+,32-,37-,39+,40-,41-,43+/m0/s1",ZNVPSQNWXWZTCK-XFZLWYIWSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(indolin-3-ylmethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,8,12,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101052584,,N/A,https://www.frdc.com.au/Archived-Reports/FRDC%20Projects/Conference%20Abstracts.pdf,,n.a.,n.a.,n.a.,,Stereochemistry is presumed to be well-defined based on use of 2D-NMR for characterisation.
CyanoMetDB_1830,"[D-Ser1,D-Asp3,Dha7]MC‐LR",,,Microcystin,C47H70N10O13,983.12,982.5123826,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CO)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O13/c1-25(2)20-34-43(64)56-35(46(68)69)23-39(60)52-32(14-11-19-50-47(48)49)42(63)53-31(16-15-26(3)21-27(4)37(70-7)22-30-12-9-8-10-13-30)28(5)40(61)54-33(45(66)67)17-18-38(59)51-29(6)41(62)57-36(24-58)44(65)55-34/h8-10,12-13,15-16,21,25,27-28,31-37,58H,6,11,14,17-20,22-24H2,1-5,7H3,(H,51,59)(H,52,60)(H,53,63)(H,54,61)(H,55,65)(H,56,64)(H,57,62)(H,66,67)(H,68,69)(H4,48,49,50)/b16-15+,26-21+/t27-,28-,31-,32-,33+,34-,35+,36+,37-/m0/s1",PFBNCGWLTHYUQJ-VPQOBCRSSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-19-methyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684719,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Microcystis,viridis,[Microcystis viridis]NIES102,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1831,[Dha7]MC-EE(OMe),[Dha7]MC-EE(OMe),,Microcystin,C47H65N7O16,984.06,983.4487794,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H65N7O16/c1-24(22-25(2)35(69-7)23-30-12-10-9-11-13-30)14-15-31-26(3)40(59)53-34(46(65)66)16-19-36(55)48-28(5)42(61)49-29(6)43(62)52-32(17-20-37(56)57)45(64)54-39(47(67)68)27(4)41(60)51-33(44(63)50-31)18-21-38(58)70-8/h9-15,22,25-27,29,31-35,39H,5,16-21,23H2,1-4,6-8H3,(H,48,55)(H,49,61)(H,50,63)(H,51,60)(H,52,62)(H,53,59)(H,54,64)(H,56,57)(H,65,66)(H,67,68)/b15-14+,24-22+/t25-,26-,27-,29+,31-,32-,33-,34+,35-,39+/m0/s1",JOQXNOGRNWPZHJ-AFNORIDRSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(2-carboxyethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-methoxy-3-oxopropyl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683843,,10.1021/tx970120t,https://pubs.acs.org/doi/10.1021/tx970120t,"Seven New Microcystins Possessing Two Glutamic Acid Units Isolated from Anabaena sp. Strain 186;Chemical Research in Toxicology;11;2;;1998;journalArticle;10.1021/tx970120t;Namikoshi, Michio; Yuan, Moucun; Sivonen, Kaarina; Carmichael, Wayne W.; Rinehart, Kenneth L.; Rouhiainen, Leo; Sun, Furong; Brittain, Scott; Otsuki, Akira",Anabaena,n.a.,[Anabaena sp.]186,,Chirality thoroughly evaluated using Waters Pico-Tag / chiral GC amino acid analysis.
CyanoMetDB_1832,"[D-Asp3,Dha7]MC-E(OMe)E(OMe)",,,Microcystin,C47H65N7O16,984.06,983.4487794,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)OC)NC(=O)C[C@@H](NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H65N7O16/c1-25(22-26(2)36(68-6)23-30-12-10-9-11-13-30)14-15-31-27(3)41(59)53-34(46(64)65)16-19-37(55)48-28(4)42(60)49-29(5)43(61)52-33(18-21-40(58)70-8)45(63)54-35(47(66)67)24-38(56)50-32(44(62)51-31)17-20-39(57)69-7/h9-15,22,26-27,29,31-36H,4,16-21,23-24H2,1-3,5-8H3,(H,48,55)(H,49,60)(H,50,56)(H,51,62)(H,52,61)(H,53,59)(H,54,63)(H,64,65)(H,66,67)/b15-14+,25-22+/t26-,27-,29+,31-,32-,33-,34+,35+,36-/m0/s1",HWVHMIUFTWETCB-NPBCHJBDSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8,15-bis(3-methoxy-3-oxopropyl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683844,,10.1021/tx970120t,https://pubs.acs.org/doi/10.1021/tx970120t,"Seven New Microcystins Possessing Two Glutamic Acid Units Isolated from Anabaena sp. Strain 186;Chemical Research in Toxicology;11;2;;1998;journalArticle;10.1021/tx970120t;Namikoshi, Michio; Yuan, Moucun; Sivonen, Kaarina; Carmichael, Wayne W.; Rinehart, Kenneth L.; Rouhiainen, Leo; Sun, Furong; Brittain, Scott; Otsuki, Akira",Anabaena,n.a.,[Anabaena sp.]186,,Chirality thoroughly evaluated using Waters Pico-Tag / chiral GC amino acid analysis.
CyanoMetDB_1833,"[D-Asp3,Ser7]MC-LR",demethyl-[L-Ser7]MC-LR; demethyl-[Ser7]MC-LR,,Microcystin,C47H72N10O13,985.13,984.5280327,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)[C@H](CO)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H72N10O13/c1-25(2)20-34-43(64)57-35(46(68)69)23-39(60)52-32(14-11-19-50-47(48)49)42(63)54-31(16-15-26(3)21-27(4)37(70-7)22-30-12-9-8-10-13-30)28(5)40(61)55-33(45(66)67)17-18-38(59)53-36(24-58)44(65)51-29(6)41(62)56-34/h8-10,12-13,15-16,21,25,27-29,31-37,58H,11,14,17-20,22-24H2,1-7H3,(H,51,65)(H,52,60)(H,53,59)(H,54,63)(H,55,61)(H,56,62)(H,57,64)(H,66,67)(H,68,69)(H4,48,49,50)/b16-15+,26-21+/t27-,28-,29+,31-,32-,33+,34-,35+,36-,37-/m0/s1",YWSITNAXFNIQML-MJDATHQWSA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684720,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Anabaena,n.a.,[Anabaena sp.]66A,,Stereochemistry assumed based on other MC congeners. The exact location of the demethylation is assumed based on other MC congeners. Cited reference reports the compound without defining the possible location of demethylation.
CyanoMetDB_1834,"[D-Leu1,D-Asp3]MC-LR",,,Microcystin,C51H78N10O12,1023.22,1022.580068,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H78N10O12/c1-28(2)23-38-47(67)59-39(24-29(3)4)48(68)60-40(50(71)72)27-42(62)55-36(17-14-22-54-51(52)53)46(66)56-35(19-18-30(5)25-31(6)41(73-10)26-34-15-12-11-13-16-34)32(7)44(64)57-37(49(69)70)20-21-43(63)61(9)33(8)45(65)58-38/h11-13,15-16,18-19,25,28-29,31-32,35-41H,8,14,17,20-24,26-27H2,1-7,9-10H3,(H,55,62)(H,56,66)(H,57,64)(H,58,65)(H,59,67)(H,60,68)(H,69,70)(H,71,72)(H4,52,53,54)/b19-18+,30-25+/t31-,32-,35-,36-,37+,38+,39-,40+,41-/m0/s1",AVSMHCMQBTVLHC-IBQQIYNOSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683869,,10.1002/rcm.7098,http://doi.wiley.com/10.1002/rcm.7098,"Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - unambiguous assignment of product ions by tandem mass spectrometry: Discovery of microcystins by MS/MS;Rapid Communications in Mass Spectrometry;29;2;;2015;journalArticle;10.1002/rcm.7098;Qi, Yulin; Rosso, Lorena; Sedan, Daniela; Giannuzzi, Leda; Andrinolo, Dario; Volmer, Dietrich A.",n.a.,n.a.,n.a.,"field sample, isolated M. aeruginosa from drainage canal of a sewage treatment facility in Pila town (35°59’49’’S, 58°08’11’’W), Buenos Aires province , Argentina",Stereochemistry assumed based on other MC congeners (identification by MS only). Also detected in Peltigera degenii (lichen species)
CyanoMetDB_1835,MC-FL,MC-FL,,Microcystin,C52H71N7O12,986.16,985.516071,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H71N7O12/c1-29(2)25-40-49(65)54-38(22-21-30(3)26-31(4)42(71-10)28-37-19-15-12-16-20-37)32(5)45(61)55-39(51(67)68)23-24-43(60)59(9)35(8)48(64)53-34(7)47(63)57-41(27-36-17-13-11-14-18-36)50(66)58-44(52(69)70)33(6)46(62)56-40/h11-22,26,29,31-34,38-42,44H,8,23-25,27-28H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,61)(H,56,62)(H,57,63)(H,58,66)(H,67,68)(H,69,70)/b22-21+,30-26+/t31-,32-,33-,34+,38-,39+,40-,41-,42-,44+/m0/s1",JNMCFADRRBGAIM-QVWKUIOOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683818,,10.3390/md12115372,http://www.mdpi.com/1660-3397/12/11/5372,"High Levels of Structural Diversity Observed in Microcystins from Microcystis CAWBG11 and Characterization of Six New Microcystin Congeners;Marine Drugs;12;11;;2014;journalArticle;10.3390/md12115372;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Kaufononga, Sangata; Cary, Stephen; Hamilton, David",Microcystis ,sp.,[Microcystis sp.]CAWBG11,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1836,MC-KynA,MC‐KynA (oxidized W),,Microcystin,C50H66N8O13,987.1,986.4749345,Nc1ccccc1C(=O)C[C@@H]1NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@H](/C=CC(\C)=C\[C@H](C)[C@H](Cc2ccccc2)OC)NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC1=O)C(=O)O)C(=O)O,"InChI=1S/C50H66N8O13/c1-26(23-27(2)40(71-9)24-33-15-11-10-12-16-33)19-20-36-28(3)43(61)55-37(49(67)68)21-22-41(60)58(8)32(7)47(65)53-31(6)46(64)56-38(25-39(59)34-17-13-14-18-35(34)51)48(66)57-42(50(69)70)29(4)44(62)52-30(5)45(63)54-36/h10-20,23,27-31,36-38,40,42H,7,21-22,24-25,51H2,1-6,8-9H3,(H,52,62)(H,53,65)(H,54,63)(H,55,61)(H,56,64)(H,57,66)(H,67,68)(H,69,70)/b20-19+,26-23+/t27-,28-,29-,30-,31+,36-,37+,38-,40-,42+/m0/s1",QXEKHQIBOJQMSZ-VTPQHVAHSA-N,"8-(2-(2-aminophenyl)-2-oxoethyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis ,sp.,[Microcystis sp.]CAWBG11,,Stereochemistry assumed relative to MC-NfkA
CyanoMetDB_1837,[D-Asp3]MC-LY,,,Microcystin,C51H69N7O13,988.13,987.4953356,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H69N7O13/c1-28(2)23-39-48(65)57-41(51(69)70)27-43(60)53-40(25-35-16-18-36(59)19-17-35)49(66)54-37(20-15-29(3)24-30(4)42(71-9)26-34-13-11-10-12-14-34)31(5)45(62)55-38(50(67)68)21-22-44(61)58(8)33(7)47(64)52-32(6)46(63)56-39/h10-20,24,28,30-32,37-42,59H,7,21-23,25-27H2,1-6,8-9H3,(H,52,64)(H,53,60)(H,54,66)(H,55,62)(H,56,63)(H,57,65)(H,67,68)(H,69,70)/b20-15+,29-24+/t30-,31-,32+,37-,38+,39-,40-,41+,42-/m0/s1",HKCABZRGOQVKMF-XMKUQBJCSA-N,"15-(4-hydroxybenzyl)-8-isobutyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802089,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,sp.,[Microcystis sp.]CYA548,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1838,[NMe-Ser7]MC‐YR,[Ser(NMe)7]MC‐YR; [Mser7]MC-YR,,Microcystin,C52H74N10O14,1063.2,1062.538597,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H74N10O14/c1-28(24-29(2)41(76-7)26-33-12-9-8-10-13-33)15-20-36-30(3)44(66)59-38(50(72)73)21-22-42(65)62(6)40(27-63)49(71)56-32(5)46(68)60-39(25-34-16-18-35(64)19-17-34)48(70)61-43(51(74)75)31(4)45(67)58-37(47(69)57-36)14-11-23-55-52(53)54/h8-10,12-13,15-20,24,29-32,36-41,43,63-64H,11,14,21-23,25-27H2,1-7H3,(H,56,71)(H,57,69)(H,58,67)(H,59,66)(H,60,68)(H,61,70)(H,72,73)(H,74,75)(H4,53,54,55)/b20-15+,28-24+/t29-,30-,31-,32+,36-,37-,38+,39-,40-,41-,43+/m0/s1",VCGGYPLSRQMFSB-SNPRYZSRSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683855,,10.1016/j.watres.2010.02.018,https://linkinghub.elsevier.com/retrieve/pii/S0043135410001351,"Spatial isolation favours the divergence in microcystin net production by Microcystis in Ugandan freshwater lakes;Water Research;44;9;;2010;journalArticle;10.1016/j.watres.2010.02.018;Okello, William; Ostermaier, Veronika; Portmann, Cyril; Gademann, Karl; Kurmayer, Rainer",Microcystis,sp.,[Microcystis sp.]AB2011/53 (isolated from Hartbeespoort Dam),,Water samples from freshwater lakes in Uganda (MS2 available in the article) [Okello et al.]. MS2 data available in article.
CyanoMetDB_1839,"[Gly1,D-Asp³,ADMAdda5,Dhb7]MC‐LR",,,Microcystin,C48H70N10O13,995.13,994.5123826,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)CCCNC(=N)N,"InChI=1S/C48H70N10O13/c1-8-32-43(64)52-25-41(62)55-36(21-26(2)3)45(66)58-37(47(69)70)24-40(61)54-34(15-12-20-51-48(49)50)44(65)56-33(29(6)42(63)57-35(46(67)68)18-19-39(60)53-32)17-16-27(4)22-28(5)38(71-30(7)59)23-31-13-10-9-11-14-31/h8-11,13-14,16-17,22,26,28-29,33-38H,12,15,18-21,23-25H2,1-7H3,(H,52,64)(H,53,60)(H,54,61)(H,55,62)(H,56,65)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,49,50,51)/b17-16+,27-22+,32-8?/t28-,29-,33-,34-,35+,36-,37+,38-/m0/s1",KFIUIFFHYOQVQQ-FMOMRVHJSA-N,"(8S,11R,15S,18S,19S,22R,Z)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-2-ethylidene-15-(3-guanidinopropyl)-8-isobutyl-19-methyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)","Detected in two hydro-terrestrial cyanobacterial mat samples collected from Miers Valley in the McMurdo Dry Valleys, Antarctica. Stereochemistry defined by amino acid analysis. Undefined E/Z isomerism at Dhb."
CyanoMetDB_1840,"[D‐Asp³,ADMAdda5]MC‐VR",,,Microcystin,C48H70N10O13,995.13,994.5123826,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(C)C)C(=O)O,"InChI=1S/C48H70N10O13/c1-25(2)40-45(66)56-36(47(69)70)24-38(60)53-34(16-13-21-51-48(49)50)44(65)54-33(18-17-26(3)22-27(4)37(71-31(8)59)23-32-14-11-10-12-15-32)28(5)41(62)55-35(46(67)68)19-20-39(61)58(9)30(7)43(64)52-29(6)42(63)57-40/h10-12,14-15,17-18,22,25,27-29,33-37,40H,7,13,16,19-21,23-24H2,1-6,8-9H3,(H,52,64)(H,53,60)(H,54,65)(H,55,62)(H,56,66)(H,57,63)(H,67,68)(H,69,70)(H4,49,50,51)/b18-17+,26-22+/t27-,28-,29+,33-,34-,35+,36+,37-,40-/m0/s1",HISFNJANPCSYHI-VVVSBFLZSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-7-(cyclohexa-1,5-dien-1-yl)-3,5-dimethylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-isopropyl-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684721,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1841,"[D-Asp3,ADMAdda5,Dha7]MC-LR",,,Microcystin,C48H70N10O13,995.13,994.5123826,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C48H70N10O13/c1-25(2)21-36-45(66)58-37(47(69)70)24-40(61)54-34(15-12-20-51-48(49)50)44(65)55-33(17-16-26(3)22-27(4)38(71-31(8)59)23-32-13-10-9-11-14-32)28(5)41(62)56-35(46(67)68)18-19-39(60)52-29(6)42(63)53-30(7)43(64)57-36/h9-11,13-14,16-17,22,25,27-28,30,33-38H,6,12,15,18-21,23-24H2,1-5,7-8H3,(H,52,60)(H,53,63)(H,54,61)(H,55,65)(H,56,62)(H,57,64)(H,58,66)(H,67,68)(H,69,70)(H4,49,50,51)/b17-16+,26-22+/t27-,28-,30+,33-,34-,35+,36-,37+,38-/m0/s1",PEAMJSDEWPXKFC-ZXQKFZIYSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-isobutyl-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684722,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1842,"[Gly1,D-Asp3,ADMAdda5]MC-LR",,,Microcystin,C48H70N10O13,995.13,994.51238,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C48H70N10O13/c1-26(2)21-36-45(66)57-37(47(69)70)24-39(60)53-34(15-12-20-51-48(49)50)44(65)55-33(17-16-27(3)22-28(4)38(71-31(7)59)23-32-13-10-9-11-14-32)29(5)42(63)56-35(46(67)68)18-19-41(62)58(8)30(6)43(64)52-25-40(61)54-36/h9-11,13-14,16-17,22,26,28-29,33-38H,6,12,15,18-21,23-25H2,1-5,7-8H3,(H,52,64)(H,53,60)(H,54,61)(H,55,65)(H,56,63)(H,57,66)(H,67,68)(H,69,70)(H4,49,50,51)/b17-16+,27-22+/t28-,29-,33-,34-,35+,36-,37+,38-/m0/s1",BUNWICSOQSWSFW-HPRKGSLFSA-N,"(8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-isobutyl-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683834,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",n.a.,n.a.,n.a.,"field samples, from various benthic mats",From Antarctica. Compound MC-5 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1843,MC-YM(O),,,Microcystin,C51H69N7O14S,1036.2,1035.462321,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCS(C)=O)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H69N7O14S/c1-28(25-29(2)41(72-8)27-34-13-11-10-12-14-34)15-20-37-30(3)44(61)55-39(50(67)68)21-22-42(60)58(7)33(6)47(64)52-32(5)46(63)56-40(26-35-16-18-36(59)19-17-35)49(66)57-43(51(69)70)31(4)45(62)54-38(48(65)53-37)23-24-73(9)71/h10-20,25,29-32,37-41,43,59H,6,21-24,26-27H2,1-5,7-9H3,(H,52,64)(H,53,65)(H,54,62)(H,55,61)(H,56,63)(H,57,66)(H,67,68)(H,69,70)/b20-15+,28-25+/t29-,30-,31-,32+,37-,38-,39+,40-,41-,43+,73?/m0/s1",UIWFJMNTVWNHGQ-PWIVRUSVSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-15-(2-(methylsulfinyl)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684877,,10.1016/j.envpol.2010.06.018,https://linkinghub.elsevier.com/retrieve/pii/S026974911000237X,"Identification of microcystins from three collection strains of Microcystis aeruginosa;Environmental Pollution;158;9;;2010;journalArticle;10.1016/j.envpol.2010.06.018;del Campo, Francisca F.; Ouahid, Youness",Microcystis,aeruginosa,UTEX 2670,,Sterochemistry of all but the M(O) group was defined by Botes et al. 1985; [Elleman 1985] [Microcystis]aeruginosa; [Botes 1985] [Microcystis]aeruginosa; [del Campo 2010] [Microcystis]aeruginosa UTEX 2670
CyanoMetDB_1844,MC-YR ,,,Microcystin,C52H72N10O13,1045.19,1044.528033,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O13/c1-28(25-29(2)41(75-8)27-34-13-10-9-11-14-34)16-21-37-30(3)44(65)59-39(50(71)72)22-23-42(64)62(7)33(6)47(68)56-32(5)46(67)60-40(26-35-17-19-36(63)20-18-35)49(70)61-43(51(73)74)31(4)45(66)58-38(48(69)57-37)15-12-24-55-52(53)54/h9-11,13-14,16-21,25,29-32,37-41,43,63H,6,12,15,22-24,26-27H2,1-5,7-8H3,(H,56,68)(H,57,69)(H,58,66)(H,59,65)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-16+,28-25+/t29-,30-,31-,32+,37-,38-,39+,40-,41-,43+/m0/s1",OWHASZQTEFAUJC-GJRPNUFSSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6437088,,10.1039/p19850002747,http://xlink.rsc.org/?DOI=p19850002747,"Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa;Journal of the Chemical Society, Perkin Transactions 1;;;;1985;journalArticle;10.1039/p19850002747;Botes, Dawie P.; Wessels, Philippus L.; Kruger, Hel�ne; Runnegar, Maria T. C.; Santikarn, Sitthivet; Smith, Richard J.; Barna, Jennifer C. J.; Williams, Dudley H.",Microcystis,aeruginosa,n.a.,,"Partial data also in https://doi.org/10.1016/0041-0101(88)90163-8, full assignments in http://dx.doi.org/10.1016/j.toxicon.2013.03.016. Microcystis aeruginosa was isolated from toxic bloom in Witbank Dam in May 1976."
CyanoMetDB_1845,"[D-Asp3,ADMAdda5]MC-LHar",,Microcystin YR,Microcystin,C50H74N10O13,1023.18,1022.543683,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C50H74N10O13/c1-27(2)23-38-47(68)59-39(49(71)72)26-41(62)55-36(17-13-14-22-53-50(51)52)46(67)56-35(19-18-28(3)24-29(4)40(73-33(8)61)25-34-15-11-10-12-16-34)30(5)43(64)57-37(48(69)70)20-21-42(63)60(9)32(7)45(66)54-31(6)44(65)58-38/h10-12,15-16,18-19,24,27,29-31,35-40H,7,13-14,17,20-23,25-26H2,1-6,8-9H3,(H,54,66)(H,55,62)(H,56,67)(H,57,64)(H,58,65)(H,59,68)(H,69,70)(H,71,72)(H4,51,52,53)/b19-18+,28-24+/t29-,30-,31+,35-,36-,37+,38-,39+,40-/m0/s1",WJEBNDAWEAQNLR-KDMHZOGOSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-8-isobutyl-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6441259,DTXSID00880086,10.1128/AEM.56.9.2650-2657.1990,https://AEM.asm.org/content/56/9/2650,"Isolation and characterization of hepatotoxic microcystin homologs from the filamentous freshwater cyanobacterium Nostoc sp. strain 152.;Applied and Environmental Microbiology;56;9;;1990;journalArticle;10.1128/AEM.56.9.2650-2657.1990;Sivonen, K; Carmichael, W W; Namikoshi, M; Rinehart, K L; Dahlem, A M; Niemelä, S I",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry well defined through chiral amino acid analyses.
CyanoMetDB_1846,[Dha7]MC-HilR,,,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C[C@@H](C)CC)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O12/c1-10-26(2)24-37-46(66)59-40(48(69)70)30(6)42(62)56-35(17-14-22-52-49(50)51)45(65)55-34(19-18-27(3)23-28(4)38(71-9)25-33-15-12-11-13-16-33)29(5)41(61)57-36(47(67)68)20-21-39(60)53-31(7)43(63)54-32(8)44(64)58-37/h11-13,15-16,18-19,23,26,28-30,32,34-38,40H,7,10,14,17,20-22,24-25H2,1-6,8-9H3,(H,53,60)(H,54,63)(H,55,65)(H,56,62)(H,57,61)(H,58,64)(H,59,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-23+/t26-,28-,29-,30-,32+,34-,35-,36+,37-,38-,40+/m0/s1",SHJJNWJJWOOLFA-WKOHKIDGSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684734,,10.1007/s00216-008-2040-x,http://link.springer.com/10.1007/s00216-008-2040-x,"NIES certified reference material for microcystins, hepatotoxic cyclic peptide toxins from cyanobacterial blooms in eutrophic water bodies;Analytical and Bioanalytical Chemistry;391;6;;2008;journalArticle;10.1007/s00216-008-2040-x;Sano, Tomoharu; Takagi, Hiroo; Nishikawa, Masataka; Kaya, Kunimitsu",Microcystis,aeruginosa,[Microcystis aeruginosa]NIES CRM No. 26,,Comprehensive analysis applied for characterisation.
CyanoMetDB_1847,"[D‐Asp³,(E)-Dhb7]MC‐HilR",,,Microcystin,C49H74N10O12,995.17,994.5487682,O=C(N/C(C(N[C@@H](C1=O)C)=O)=C/C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)C[C@@H](C)CC)=O)=O)=O)=O,"InChI=1S/C49H74N10O12/c1-9-27(3)24-37-46(66)59-38(48(69)70)26-41(61)55-35(17-14-22-52-49(50)51)45(65)56-34(19-18-28(4)23-29(5)39(71-8)25-32-15-12-11-13-16-32)30(6)42(62)57-36(47(67)68)20-21-40(60)54-33(10-2)44(64)53-31(7)43(63)58-37/h10-13,15-16,18-19,23,27,29-31,34-39H,9,14,17,20-22,24-26H2,1-8H3,(H,53,64)(H,54,60)(H,55,61)(H,56,65)(H,57,62)(H,58,63)(H,59,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,28-23+,33-10+/t27-,29-,30-,31+,34-,35-,36+,37-,38+,39-/m0/s1",CJBURLKHSGYKKJ-LOEFFASASA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-8-((S)-2-methylbutyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",11193981,,10.1016/j.phytochem.2004.03.034,https://linkinghub.elsevier.com/retrieve/pii/S0031942204001918,"A Dhb-microcystin from the filamentous cyanobacterium Planktothrix rubescens;Phytochemistry;65;14;;2004;journalArticle;10.1016/j.phytochem.2004.03.034;Sano, Tomoharu; Takagi, Hiroo; Kaya, Kunimitsu",Oscillatoria/Planktothrix,rubescens,[Oscillatoria/Planktothrix rubescens]CCAP 1459/14,,
CyanoMetDB_1848,"[D-Asp3,D-MeO-Glu6]MC-LR","[D-Asp3,D-Glu(OMe)6]MC-LR",,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)OC)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O12/c1-27(2)23-37-46(66)58-38(47(67)68)26-40(60)54-35(17-14-22-52-49(50)51)45(65)55-34(19-18-28(3)24-29(4)39(70-9)25-33-15-12-11-13-16-33)30(5)42(62)56-36(48(69)71-10)20-21-41(61)59(8)32(7)44(64)53-31(6)43(63)57-37/h11-13,15-16,18-19,24,27,29-31,34-39H,7,14,17,20-23,25-26H2,1-6,8-10H3,(H,53,64)(H,54,60)(H,55,65)(H,56,62)(H,57,63)(H,58,66)(H,67,68)(H4,50,51,52)/b19-18+,28-24+/t29-,30-,31+,34-,35-,36+,37-,38+,39-/m0/s1",TWEYNHXDPXMESM-QYZWFTJFSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",101644064,,10.1016/0041-0101(92)90522-7,https://linkinghub.elsevier.com/retrieve/pii/0041010192905227,"Two methyl ester derivatives of microcystins, cyclic heptapeptide hepatotoxins, isolated from Anabaena flos-aquae strain CYA 83/1;Toxicon;30;11;;1992;journalArticle;10.1016/0041-0101(92)90522-7;Sivonen, Kaarina; Skulberg, Olav M.; Namikoshi, Michio; Evans, William R.; Carmichael, Wayne W.; Rinehart, Kenneth L.",Anabaena/Dolichospermum,flos aquae,CYA 83/1,,"Structure determined using a combination of FAB-MS(/MS), Waters Pico-tag amino acid analyser (amino acid chiral determination). No NMR applied. Note, dried biomass was extracted using methanol-containing solution - potential extraction artefact?"
CyanoMetDB_1849,"[D-Asp³,Dhb7]MC‐AhaR","[D-Asp³,Dhb7]MC‐AhaR or could be [D-Asp3,Dhb7]MC-HilR",,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCCC)NC(=O)[C@@H](C)NC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O12/c1-8-10-12-18-36-46(66)59-38(48(69)70)27-41(61)55-35(19-15-24-52-49(50)51)45(65)56-34(21-20-28(3)25-29(4)39(71-7)26-32-16-13-11-14-17-32)30(5)42(62)58-37(47(67)68)22-23-40(60)54-33(9-2)44(64)53-31(6)43(63)57-36/h9,11,13-14,16-17,20-21,25,29-31,34-39H,8,10,12,15,18-19,22-24,26-27H2,1-7H3,(H,53,64)(H,54,60)(H,55,61)(H,56,65)(H,57,63)(H,58,62)(H,59,66)(H,67,68)(H,69,70)(H4,50,51,52)/b21-20+,28-25+,33-9?/t29-,30-,31+,34-,35-,36-,37+,38+,39-/m0/s1",IHQWIGUDUPUIKA-JZRHOFFSSA-N,"(E)-15-(3-((diaminomethylene)amino)propyl)-2-ethylidene-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-8-pentyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",,,10.1021/es305202p,https://pubs.acs.org/doi/10.1021/es305202p,"LC-MS Analysis with Thiol Derivatization to Differentiate [Dhb 7 ]- from [Mdha 7 ]-Microcystins: Analysis of Cyanobacterial Blooms, Planktothrix Cultures and European Crayfish from Lake Steinsfjorden, Norway;Environmental Science & Technology;47;9;;2013;journalArticle;10.1021/es305202p;Miles, Christopher O.; Sandvik, Morten; Haande, Sigrid; Nonga, Hezron; Ballot, Andreas",n.a.,n.a.,n.a.,"field samples, Planktothrix cultures from Lake Steinsfjorden, Norway","Tentative annotation (could also be [D-Asp3, Dhb7]MC-HilR. Stereochemistry assumed based on other microcystin structures. Structural descriptors are for 2-aminoheptanoic acid moiety in position 2. Detected in a concentrated phytoplankton sample derived from a net sample (25 μm mesh) taken from L. Steinsfjorden, Norway - Planktothrix agardhii was reported as major species in epilimnion (0-7 m), but was only moderately abundant in the metalimnion (8-14 m)."
CyanoMetDB_1850,[DMAdda5]MC‐HilR,,,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C[C@@H](C)CC)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C49H74N10O12/c1-10-26(2)24-37-46(67)58-40(48(70)71)30(6)42(63)55-35(17-14-22-52-49(50)51)45(66)54-34(19-18-27(3)23-28(4)38(60)25-33-15-12-11-13-16-33)29(5)41(62)56-36(47(68)69)20-21-39(61)59(9)32(8)44(65)53-31(7)43(64)57-37/h11-13,15-16,18-19,23,26,28-31,34-38,40,60H,8,10,14,17,20-22,24-25H2,1-7,9H3,(H,53,65)(H,54,66)(H,55,63)(H,56,62)(H,57,64)(H,58,67)(H,68,69)(H,70,71)(H4,50,51,52)/b19-18+,27-23+/t26-,28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",HWPKSGNNNYHECD-LNFSOKIGSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684723,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]IO-102-I,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1851,[DMAdda5]MC‐LHar,,,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C49H74N10O12/c1-26(2)23-37-46(67)58-40(48(70)71)30(6)42(63)55-35(17-13-14-22-52-49(50)51)45(66)54-34(19-18-27(3)24-28(4)38(60)25-33-15-11-10-12-16-33)29(5)41(62)56-36(47(68)69)20-21-39(61)59(9)32(8)44(65)53-31(7)43(64)57-37/h10-12,15-16,18-19,24,26,28-31,34-38,40,60H,8,13-14,17,20-23,25H2,1-7,9H3,(H,53,65)(H,54,66)(H,55,63)(H,56,62)(H,57,64)(H,58,67)(H,68,69)(H,70,71)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",RZJXAEDFXOQJKZ-GWRQVWKTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(4-guanidinobutyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-isobutyl-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684724,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1852,MC‐RL,,,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O12/c1-26(2)23-37-46(66)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)55-35(17-14-22-52-49(50)51)45(65)58-40(48(69)70)30(6)42(62)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,66)(H,55,63)(H,56,61)(H,57,62)(H,58,65)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",JHVINXDONYNELG-GWRQVWKTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(3-guanidinopropyl)-15-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684756,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry assumed based on other MC congeners. Annotation based on MS analysis of native and thiol-derivatised compound using precursor ion scanning and data-dependent MS/MS approaches, plus similarity of structure to a 1D and 2D-NMR-analysed MC-RY compound."
CyanoMetDB_1853,[D-Asp3]MC-ER,,,Microcystin,C47H68N10O14,997.1,996.4916469,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H68N10O14/c1-25(22-26(2)36(71-7)23-30-12-9-8-10-13-30)15-16-31-27(3)40(62)55-34(45(67)68)17-19-38(59)57(6)29(5)42(64)51-28(4)41(63)54-33(18-20-39(60)61)44(66)56-35(46(69)70)24-37(58)52-32(43(65)53-31)14-11-21-50-47(48)49/h8-10,12-13,15-16,22,26-28,31-36H,5,11,14,17-21,23-24H2,1-4,6-7H3,(H,51,64)(H,52,58)(H,53,65)(H,54,63)(H,55,62)(H,56,66)(H,60,61)(H,67,68)(H,69,70)(H4,48,49,50)/b16-15+,25-22+/t26-,27-,28+,31-,32-,33-,34+,35+,36-/m0/s1",AHXOFCOHTAKFKX-KAXOOBBASA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-(2-carboxyethyl)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683812,,10.3390/md17110643,https://www.mdpi.com/1660-3397/17/11/643,"Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling;Marine Drugs;17;11;;2019;journalArticle;10.3390/md17110643;Mallia, Vittoria; Uhlig, Silvio; Rafuse, Cheryl; Meija, Juris; Miles, Christopher O.",Planktothrix ,prolifica ,NIVA-CYA 544,,
CyanoMetDB_1854,MC-WAba,MC-WAbu,,Microcystin,C52H68N8O12,997.14,996.4956699,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H68N8O12/c1-10-37-49(66)56-38(21-20-28(2)24-29(3)42(72-9)25-34-16-12-11-13-17-34)30(4)45(62)57-40(51(68)69)22-23-43(61)60(8)33(7)48(65)54-32(6)47(64)58-41(26-35-27-53-39-19-15-14-18-36(35)39)50(67)59-44(52(70)71)31(5)46(63)55-37/h11-21,24,27,29-32,37-38,40-42,44,53H,7,10,22-23,25-26H2,1-6,8-9H3,(H,54,65)(H,55,63)(H,56,66)(H,57,62)(H,58,64)(H,59,67)(H,68,69)(H,70,71)/b21-20+,28-24+/t29-,30-,31-,32+,37-,38-,40+,41-,42-,44+/m0/s1",NKNOACROYYAXRI-SWBRTAFISA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-ethyl-8-(indolin-3-ylmethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802225,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Determined by LC-MS/MS. Stereochemistry assumed based on related compound from same extract that was analysed by 1- and 2-D NMR spectroscopy. Detected as [M+Na]+ form.
CyanoMetDB_1855,[NMe-Ala7]MC-LR,[L-NMe-Ala7]MC-LR,,Microcystin,C49H76N10O12,997.19,996.5644182,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)CC(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H76N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-32,34-38,40H,14,17,20-23,25H2,1-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,32-,34-,35-,36+,37-,38-,40+/m0/s1",XVXFRYMCSIZPFI-CMNXQPOWSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-isobutyl-1,2,5,12,19-pentamethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802429,,10.1021/tx00032a003,https://pubs.acs.org/doi/abs/10.1021/tx00032a003,"Chemical characterization and toxicity of dihydro derivatives of nodularin and microcystin-LR, potent cyanobacterial cyclic peptide hepatotoxins;Chemical Research in Toxicology;6;2;;1993;journalArticle;10.1021/tx00032a003;Namikoshi, Michio; Choi, Byoung Wook; Sun, Furong; Rinehart, Kenneth L.; Evans, William R.; Carmichael, Wayne W.",Microcystis,aeruginosa,[Microcystis aeruginosa]PCC7820,,"semi-synthetically produced - the parent compound was isolated by solid-phase and liquid chromatography, before chemical modification."
CyanoMetDB_1856,[Dha7]MC-E(OMe)E(OMe),,,Microcystin,C48H67N7O16,998.08,997.4644294,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H67N7O16/c1-25(23-26(2)36(69-7)24-31-13-11-10-12-14-31)15-16-32-27(3)41(59)54-35(47(65)66)17-20-37(56)49-29(5)43(61)50-30(6)44(62)53-34(19-22-39(58)71-9)46(64)55-40(48(67)68)28(4)42(60)52-33(45(63)51-32)18-21-38(57)70-8/h10-16,23,26-28,30,32-36,40H,5,17-22,24H2,1-4,6-9H3,(H,49,56)(H,50,61)(H,51,63)(H,52,60)(H,53,62)(H,54,59)(H,55,64)(H,65,66)(H,67,68)/b16-15+,25-23+/t26-,27-,28-,30+,32-,33-,34-,35+,36-,40+/m0/s1",RODJROXYYNRFDY-GHJXESGZSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8,15-bis(3-methoxy-3-oxopropyl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683845,,10.1021/tx970120t,https://pubs.acs.org/doi/10.1021/tx970120t,"Seven New Microcystins Possessing Two Glutamic Acid Units Isolated from Anabaena sp. Strain 186;Chemical Research in Toxicology;11;2;;1998;journalArticle;10.1021/tx970120t;Namikoshi, Michio; Yuan, Moucun; Sivonen, Kaarina; Carmichael, Wayne W.; Rinehart, Kenneth L.; Rouhiainen, Leo; Sun, Furong; Brittain, Scott; Otsuki, Akira",Anabaena,n.a.,[Anabaena sp.]186,,Chirality thoroughly evaluated using Waters Pico-Tag / chiral GC amino acid analysis.
CyanoMetDB_1857,MC-OiaA,,,Microcystin,C51H66N8O13,999.12,998.4749345,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC2c3ccccc3NC2=O)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H66N8O13/c1-26(23-27(2)40(72-9)24-33-15-11-10-12-16-33)19-20-36-28(3)43(61)56-38(50(68)69)21-22-41(60)59(8)32(7)47(65)53-31(6)46(64)57-39(25-35-34-17-13-14-18-37(34)55-48(35)66)49(67)58-42(51(70)71)29(4)44(62)52-30(5)45(63)54-36/h10-20,23,27-31,35-36,38-40,42H,7,21-22,24-25H2,1-6,8-9H3,(H,52,62)(H,53,65)(H,54,63)(H,55,66)(H,56,61)(H,57,64)(H,58,67)(H,68,69)(H,70,71)/b20-19+,26-23+/t27-,28-,29-,30-,31+,35?,36-,38+,39-,40-,42+/m0/s1",HNAQQSWIMKHJPV-USSSJJRQSA-N,"18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-((2-oxoindolin-3-yl)methyl)-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683822,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Structure assigned through LC-MS/MS and HR-ESI-MS analyses. Stereochemistry assumed relative to MC-NfkA which was analysed by 1D and 2D-NMR techniques.
CyanoMetDB_1858,[D-Asp³]MC‐MR,,,Microcystin,C47H70N10O12S,999.18,998.4895387,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O12S/c1-26(23-27(2)37(69-7)24-31-13-10-9-11-14-31)16-17-32-28(3)40(60)55-35(45(65)66)18-19-39(59)57(6)30(5)42(62)51-29(4)41(61)54-34(20-22-70-8)44(64)56-36(46(67)68)25-38(58)52-33(43(63)53-32)15-12-21-50-47(48)49/h9-11,13-14,16-17,23,27-29,32-37H,5,12,15,18-22,24-25H2,1-4,6-8H3,(H,51,62)(H,52,58)(H,53,63)(H,54,61)(H,55,60)(H,56,64)(H,65,66)(H,67,68)(H4,48,49,50)/b17-16+,26-23+/t27-,28-,29+,32-,33-,34-,35+,36+,37-/m0/s1",SAOKRPLOVXDUIY-QTDAUVDESA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-8-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684780,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1859,[Ser7]MC-LR,[L-Ser7]MC-LR,,Microcystin,C48H74N10O13,999.16,998.5436828,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)[C@H](CO)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H74N10O13/c1-25(2)21-35-44(65)58-39(47(69)70)29(6)41(62)55-33(15-12-20-51-48(49)50)43(64)54-32(17-16-26(3)22-27(4)37(71-8)23-31-13-10-9-11-14-31)28(5)40(61)56-34(46(67)68)18-19-38(60)53-36(24-59)45(66)52-30(7)42(63)57-35/h9-11,13-14,16-17,22,25,27-30,32-37,39,59H,12,15,18-21,23-24H2,1-8H3,(H,52,66)(H,53,60)(H,54,64)(H,55,62)(H,56,61)(H,57,63)(H,58,65)(H,67,68)(H,69,70)(H4,49,50,51)/b17-16+,26-22+/t27-,28-,29-,30+,32-,33-,34+,35-,36-,37-,39+/m0/s1",PWCXBLSMFHTSOU-GUMWKJIBSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101642887,,10.1016/0041-0101(92)90521-6,https://linkinghub.elsevier.com/retrieve/pii/0041010192905216,"Two new l-serine variants of microcystins-LR and -RR from Anabaena sp. strains 202 A1 and 202 A2;Toxicon;30;11;;1992;journalArticle;10.1016/0041-0101(92)90521-6;Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Carmichael, Wayne W.; Sun, Furong; Rouhiainen, Leo; Luukkainen, Raija; Rinehart, Kenneth L.",Anabaena,n.a.,"[Anabaena sp.]202 A1, [Anabaena sp.]202 A2",,Stereochemistry defined through amino acid analysis
CyanoMetDB_1860,[seco‐4/5][D-Asp³]MC‐LR,,,Microcystin,C48H74N10O13,999.16,998.5436828,O=C(O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@@H](N)/C=C/C(/C)=C/[C@H](C)[C@@H](OC)Cc1ccccc1)C(=O)O)C(=O)O,"InChI=1S/C48H74N10O13/c1-26(2)22-36(44(64)57-37(47(69)70)25-39(59)54-34(45(65)66)16-13-21-52-48(50)51)56-42(62)30(6)53-43(63)31(7)58(8)40(60)20-19-35(46(67)68)55-41(61)29(5)33(49)18-17-27(3)23-28(4)38(71-9)24-32-14-11-10-12-15-32/h10-12,14-15,17-18,23,26,28-30,33-38H,7,13,16,19-22,24-25,49H2,1-6,8-9H3,(H,53,63)(H,54,59)(H,55,61)(H,56,62)(H,57,64)(H,65,66)(H,67,68)(H,69,70)(H4,50,51,52)/b18-17+,27-23+/t28-,29-,30+,33-,34-,35+,36-,37+,38-/m0/s1",LHOZHBTYSUFUSJ-MREVJOSWSA-N,"(29E,31E)-1,28-diamino-34-benzyl-1-imino-13-isobutyl-16,20,27,31,33-pentamethyl-19-methylene-8,12,15,18,21,26-hexaoxo-35-oxa-2,7,11,14,17,20,25-heptaazahexatriaconta-29,31-diene-6,10,24-tricarboxylic acid",146684781,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1861,[Dha7]MC-LR,,,Microcystin,C48H72N10O12,981.15,980.5331181,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC\N=C(/N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12/c1-25(2)22-36-45(65)58-39(47(68)69)29(6)41(61)55-34(16-13-21-51-48(49)50)44(64)54-33(18-17-26(3)23-27(4)37(70-9)24-32-14-11-10-12-15-32)28(5)40(60)56-35(46(66)67)19-20-38(59)52-30(7)42(62)53-31(8)43(63)57-36/h10-12,14-15,17-18,23,25,27-29,31,33-37,39H,7,13,16,19-22,24H2,1-6,8-9H3,(H,52,59)(H,53,62)(H,54,64)(H,55,61)(H,56,60)(H,57,63)(H,58,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,26-23+/t27-,28-,29-,31+,33-,34-,35+,36-,37-,39+/m0/s1",WLWITBHAANNFHV-NDUWXMRTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-((diaminomethylene)amino)propyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101642889,,10.1016/0041-0101(91)90022-J,https://linkinghub.elsevier.com/retrieve/pii/004101019190022J,"Isolation of two toxic heptapeptide microcystins from an axenic strain of Microcystis aeruginosa, K-139;Toxicon;29;43955;;1991;journalArticle;10.1016/0041-0101(91)90022-J;Harada, Ken-ichi; Ogawa, Kiyoshi; Matsuura, Kenji; Nagai, Hidetoshi; Murata, Hideaki; Suzuki, Makoto; Itezono, Yoshiko; Nakayama, Noboru; Shirai, Makoto; Nakano, Masayasu",Microcystis,aeruginosa,K-139,,"[Harada 1992]Microcystis strain isolated from field samples collected from Lake Kasumigaura, 24 Sept 1985. Stereochemistry assumed based on other MC congeners, though cited Harada 1992 reference indicates stereochemistry in structural representation. [Namikoshi 1992] Field sample isolated from Homer lake bloom (Illinois, summer, 1988) that comprised mainly Microcystis aeruginosa, as well as lower amounts of Microcystis viridis and Microcystis wesenbergii."
CyanoMetDB_1862,MC‐LHph,,,Microcystin,C53H73N7O12,1000.19,999.5317211,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCc2ccccc2)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C53H73N7O12/c1-30(2)27-42-51(67)59-45(53(70)71)34(6)47(63)56-40(24-22-37-17-13-11-14-18-37)50(66)55-39(23-21-31(3)28-32(4)43(72-10)29-38-19-15-12-16-20-38)33(5)46(62)57-41(52(68)69)25-26-44(61)60(9)36(8)49(65)54-35(7)48(64)58-42/h11-21,23,28,30,32-35,39-43,45H,8,22,24-27,29H2,1-7,9-10H3,(H,54,65)(H,55,66)(H,56,63)(H,57,62)(H,58,64)(H,59,67)(H,68,69)(H,70,71)/b23-21+,31-28+/t32-,33-,34-,35+,39-,40-,41+,42-,43-,45+/m0/s1",LVCIVARPKLCTRB-OVBXAQJQSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-15-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684762,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Phormidium,sp.,[Phormidium sp.]DVL1003c,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1863,MC‐KynAba,MC-KynAbu,,Microcystin,C51H68N8O13,1001.13,1000.490585,Nc1ccccc1C(=O)C[C@@H]1NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@H](/C=CC(\C)=C\[C@H](C)[C@H](Cc2ccccc2)OC)NC(=O)[C@H](CC)NC(=O)[C@@H](C)[C@@H](NC1=O)C(=O)O)C(=O)O,"InChI=1S/C51H68N8O13/c1-10-36-48(66)55-37(21-20-27(2)24-28(3)41(72-9)25-33-16-12-11-13-17-33)29(4)44(62)56-38(50(68)69)22-23-42(61)59(8)32(7)47(65)53-31(6)46(64)57-39(26-40(60)34-18-14-15-19-35(34)52)49(67)58-43(51(70)71)30(5)45(63)54-36/h11-21,24,28-31,36-39,41,43H,7,10,22-23,25-26,52H2,1-6,8-9H3,(H,53,65)(H,54,63)(H,55,66)(H,56,62)(H,57,64)(H,58,67)(H,68,69)(H,70,71)/b21-20+,27-24+/t28-,29-,30-,31+,36-,37-,38+,39-,41-,43+/m0/s1",RLKQRHBFVMIWTE-BWYSDFBGSA-N,"8-(2-(2-aminophenyl)-2-oxoethyl)-15-ethyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Structure assigned through LC-MS/MS and HR-ESI-MS analyses. Stereochemistry assumed relative to MC-NfkA which was analysed by 1D and 2D-NMR techniques.
CyanoMetDB_1864,"[D‐Asp3,Dha7]MC‐FR",,,Microcystin,C50H68N10O12,1001.13,1000.501818,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H68N10O12/c1-28(24-29(2)40(72-6)26-34-16-11-8-12-17-34)19-20-35-30(3)43(63)58-37(48(68)69)21-22-41(61)54-31(4)44(64)55-32(5)45(65)59-38(25-33-14-9-7-10-15-33)47(67)60-39(49(70)71)27-42(62)56-36(46(66)57-35)18-13-23-53-50(51)52/h7-12,14-17,19-20,24,29-30,32,35-40H,4,13,18,21-23,25-27H2,1-3,5-6H3,(H,54,61)(H,55,64)(H,56,62)(H,57,66)(H,58,63)(H,59,65)(H,60,67)(H,68,69)(H,70,71)(H4,51,52,53)/b20-19+,28-24+/t29-,30-,32+,35-,36-,37+,38-,39+,40-/m0/s1",NELUXDWVSZSXBG-MCVAKWTKSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-benzyl-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684725,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Anabaena,n.a.,[Anabaena sp.]66A,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1865,[L-Ser7]MC-EE(OMe),[Ser7]MC-EE(OMe),,Microcystin,C47H67N7O17,1002.07,1001.459344,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](C)NC(=O)[C@H](CO)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H67N7O17/c1-24(21-25(2)35(70-6)22-29-11-9-8-10-12-29)13-14-30-26(3)40(60)53-33(46(66)67)15-18-36(56)49-34(23-55)45(65)48-28(5)42(62)52-31(16-19-37(57)58)44(64)54-39(47(68)69)27(4)41(61)51-32(43(63)50-30)17-20-38(59)71-7/h8-14,21,25-28,30-35,39,55H,15-20,22-23H2,1-7H3,(H,48,65)(H,49,56)(H,50,63)(H,51,61)(H,52,62)(H,53,60)(H,54,64)(H,57,58)(H,66,67)(H,68,69)/b14-13+,24-21+/t25-,26-,27-,28+,30-,31-,32-,33+,34-,35-,39+/m0/s1",RCXSHZJBABBPCQ-XSTWSXKBSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-8-(2-carboxyethyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-methoxy-3-oxopropyl)-5,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683846,,10.1021/tx970120t,https://pubs.acs.org/doi/10.1021/tx970120t,"Seven New Microcystins Possessing Two Glutamic Acid Units Isolated from Anabaena sp. Strain 186;Chemical Research in Toxicology;11;2;;1998;journalArticle;10.1021/tx970120t;Namikoshi, Michio; Yuan, Moucun; Sivonen, Kaarina; Carmichael, Wayne W.; Rinehart, Kenneth L.; Rouhiainen, Leo; Sun, Furong; Brittain, Scott; Otsuki, Akira",Anabaena,n.a.,[Anabaena sp.]186,,Cited reference reports an insufficient amount was recovered to enable chirality assessment of amino acid moieties. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1866,"[D-Asp3,Ser7]MC-E(OMe)E(OMe)",,,Microcystin,C47H67N7O17,1002.07,1001.459344,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)OC)NC(=O)C[C@@H](NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)NC(=O)[C@H](CO)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H67N7O17/c1-25(21-26(2)36(69-5)22-29-11-9-8-10-12-29)13-14-30-27(3)41(60)53-33(46(65)66)15-18-37(56)50-35(24-55)45(64)48-28(4)42(61)52-32(17-20-40(59)71-7)44(63)54-34(47(67)68)23-38(57)49-31(43(62)51-30)16-19-39(58)70-6/h8-14,21,26-28,30-36,55H,15-20,22-24H2,1-7H3,(H,48,64)(H,49,57)(H,50,56)(H,51,62)(H,52,61)(H,53,60)(H,54,63)(H,65,66)(H,67,68)/b14-13+,25-21+/t26-,27-,28+,30-,31-,32-,33+,34+,35-,36-/m0/s1",ZPWBUZCVOZVOLS-FTHMBYDKSA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8,15-bis(3-methoxy-3-oxopropyl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683847,,10.1021/tx970120t,https://pubs.acs.org/doi/10.1021/tx970120t,"Seven New Microcystins Possessing Two Glutamic Acid Units Isolated from Anabaena sp. Strain 186;Chemical Research in Toxicology;11;2;;1998;journalArticle;10.1021/tx970120t;Namikoshi, Michio; Yuan, Moucun; Sivonen, Kaarina; Carmichael, Wayne W.; Rinehart, Kenneth L.; Rouhiainen, Leo; Sun, Furong; Brittain, Scott; Otsuki, Akira",Anabaena,n.a.,[Anabaena sp.]186,,"Chirality thoroughly evaluated using Waters Pico-Tag / chiral GC amino acid analysis. Compound #4 in ref. Chiral GC-MS and/or Waters Pico-Tag analyser used for amino acid analysis, therefore, assumedly amino acid L/D forms are correct. FAB-MS and ESI-MS, both with CID-based MS/MS. No NMR used for assignment of the glutamates. Assignment of E(OMe)E(OMe) was justified as: ""Since only the methyl ester among the above derivatives can give glutamic acid by the acid hydrolysis used for amino acid analysis, the two L-amino acid units were assigned as the methyl ester derivative of Glu""."
CyanoMetDB_1867,MC-(H4)YR,,,Microcystin,C52H76N10O13,1049.22,1048.559333,O=C(CC[C@@H](NC([C@H]([C@@H](NC([C@@H](NC([C@H]([C@@H](NC([C@H](C[C@]1(C=C[C@@H](CC1)O)[H])N2)=O)C(O)=O)C)=O)CCCNC(N)=N)=O)/C=C/C(C)=C/[C@@H]([C@H](CC3=CC=CC=C3)OC)C)C)=O)C(O)=O)N(C(C(N[C@H](C)C2=O)=O)=C)C,"InChI=1S/C52H76N10O13/c1-28(25-29(2)41(75-8)27-34-13-10-9-11-14-34)16-21-37-30(3)44(65)59-39(50(71)72)22-23-42(64)62(7)33(6)47(68)56-32(5)46(67)60-40(26-35-17-19-36(63)20-18-35)49(70)61-43(51(73)74)31(4)45(66)58-38(48(69)57-37)15-12-24-55-52(53)54/h9-11,13-14,16-17,19,21,25,29-32,35-41,43,63H,6,12,15,18,20,22-24,26-27H2,1-5,7-8H3,(H,56,68)(H,57,69)(H,58,66)(H,59,65)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-16+,28-25+/t29-,30-,31-,32+,35-,36-,37-,38-,39+,40-,41-,43+/m0/s1",PITACCAFEGTDMU-WPROKLQDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802265,,10.1021/jo00117a017,https://pubs.acs.org/doi/abs/10.1021/jo00117a017,"Seven More Microcystins from Homer Lake Cells: Application of the General Method for Structure Assignment of Peptides Containing .alpha.,.beta.-Dehydroamino Acid Unit(s);The Journal of Organic Chemistry;60;12;;1995;journalArticle;10.1021/jo00117a017;Namikoshi, Michio; Sun, Furong; Choi, Byoung Wook; Rinehart, Kenneth L.; Carmichael, Wayne W.; Evans, William R.; Beasley, Val R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria Microcystis aeruginosa,Detected in field samples from Homer Lake (Illinois) (M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii)
CyanoMetDB_1868,[D-Asp³]MC‐HilY,,,Microcystin,C52H71N7O13,1002.16,1001.510986,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC(C[C@H](C(O)=O)NC([C@@H](N1)C[C@@H](C)CC)=O)=O)=O)=O,"InChI=1S/C52H71N7O13/c1-10-29(2)25-40-49(66)58-42(52(70)71)28-44(61)54-41(26-36-17-19-37(60)20-18-36)50(67)55-38(21-16-30(3)24-31(4)43(72-9)27-35-14-12-11-13-15-35)32(5)46(63)56-39(51(68)69)22-23-45(62)59(8)34(7)48(65)53-33(6)47(64)57-40/h11-21,24,29,31-33,38-43,60H,7,10,22-23,25-28H2,1-6,8-9H3,(H,53,65)(H,54,61)(H,55,67)(H,56,63)(H,57,64)(H,58,66)(H,68,69)(H,70,71)/b21-16+,30-24+/t29-,31-,32-,33+,38-,39+,40-,41-,42+,43-/m0/s1",WLBVWRVOGXOSNA-SLNOSVEWSA-N,"15-(4-hydroxybenzyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-8-(2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802397,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,NIVA-CYA 548,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1869,MC‐YL,,,Microcystin,C52H71N7O13,1002.16,1001.510986,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H71N7O13/c1-28(2)24-40-49(66)54-38(21-16-29(3)25-30(4)42(72-10)27-35-14-12-11-13-15-35)31(5)45(62)55-39(51(68)69)22-23-43(61)59(9)34(8)48(65)53-33(7)47(64)57-41(26-36-17-19-37(60)20-18-36)50(67)58-44(52(70)71)32(6)46(63)56-40/h11-21,25,28,30-33,38-42,44,60H,8,22-24,26-27H2,1-7,9-10H3,(H,53,65)(H,54,66)(H,55,62)(H,56,63)(H,57,64)(H,58,67)(H,68,69)(H,70,71)/b21-16+,29-25+/t30-,31-,32-,33+,38-,39+,40-,41-,42-,44+/m0/s1",ULVKNPZLIDQRTH-WSTSHCHISA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(4-hydroxybenzyl)-15-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683865,,10.1016/j.envpol.2010.06.018,https://linkinghub.elsevier.com/retrieve/pii/S026974911000237X,"Identification of microcystins from three collection strains of Microcystis aeruginosa;Environmental Pollution;158;9;;2010;journalArticle;10.1016/j.envpol.2010.06.018;del Campo, Francisca F.; Ouahid, Youness",Microcystis,aeruginosa,[Microcystis aeruginosa]UTEX 2670,,Stereochemistry inferred based on other MC congeners.
CyanoMetDB_1870,"[D‐Asp³,Mser7]MC‐LY",,,Microcystin,C51H71N7O14,1006.15,1005.5059,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](CO)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)CC(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H71N7O14/c1-28(2)22-38-47(65)57-40(51(70)71)26-43(61)53-39(24-34-15-17-35(60)18-16-34)48(66)54-36(19-14-29(3)23-30(4)42(72-8)25-33-12-10-9-11-13-33)31(5)45(63)55-37(50(68)69)20-21-44(62)58(7)41(27-59)49(67)52-32(6)46(64)56-38/h9-19,23,28,30-32,36-42,59-60H,20-22,24-27H2,1-8H3,(H,52,67)(H,53,61)(H,54,66)(H,55,63)(H,56,64)(H,57,65)(H,68,69)(H,70,71)/b19-14+,29-23+/t30-,31-,32+,36-,37+,38-,39-,40+,41-,42-/m0/s1",CWFJBZPUEILZER-NYHXZKTISA-N,"2-hydroxy-15-(4-hydroxybenzyl)-8-isobutyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802022,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,NIVA-CYA 548,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1871,"[Gly1,D-Asp3,ADMAdda5]MC-LHar",,,Microcystin,C49H72N10O13,1009.16,1008.528032,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C49H72N10O13/c1-27(2)22-37-46(67)58-38(48(70)71)25-40(61)54-35(16-12-13-21-52-49(50)51)45(66)56-34(18-17-28(3)23-29(4)39(72-32(7)60)24-33-14-10-9-11-15-33)30(5)43(64)57-36(47(68)69)19-20-42(63)59(8)31(6)44(65)53-26-41(62)55-37/h9-11,14-15,17-18,23,27,29-30,34-39H,6,12-13,16,19-22,24-26H2,1-5,7-8H3,(H,53,65)(H,54,61)(H,55,62)(H,56,66)(H,57,64)(H,58,67)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,28-23+/t29-,30-,34-,35-,36+,37-,38+,39-/m0/s1",OGIULMWAEYWUMA-CFKDJMJKSA-N,"(8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-8-isobutyl-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683835,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",n.a.,n.a.,n.a.,"field samples, from various benthic mats",From Antarctica. Compound MC-7 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1872,[D-Asp3]MC-LF,,,Microcystin,C51H69N7O12,972.13,971.500421,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H69N7O12/c1-29(2)24-39-48(64)57-41(51(68)69)28-43(59)53-40(26-35-16-12-10-13-17-35)49(65)54-37(21-20-30(3)25-31(4)42(70-9)27-36-18-14-11-15-19-36)32(5)45(61)55-38(50(66)67)22-23-44(60)58(8)34(7)47(63)52-33(6)46(62)56-39/h10-21,25,29,31-33,37-42H,7,22-24,26-28H2,1-6,8-9H3,(H,52,63)(H,53,59)(H,54,65)(H,55,61)(H,56,62)(H,57,64)(H,66,67)(H,68,69)/b21-20+,30-25+/t31-,32-,33+,37-,38+,39-,40-,41+,42-/m0/s1",BWSABZLQEYMURK-BMUDUOPCSA-N,"15-benzyl-8-isobutyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801670,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,[Microcystis aeruginosa]PCC7820,,Stereochemistry assumed based on other MC congeners (LC-MS/MS and HRMS analyses unable to confirm this)
CyanoMetDB_1873,"[ADMAdda5,Dha7]MC‐LR",,,Microcystin,C49H72N10O13,1009.16,1008.528033,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C49H72N10O13/c1-25(2)22-37-46(67)59-40(48(70)71)29(6)42(63)56-35(16-13-21-52-49(50)51)45(66)55-34(18-17-26(3)23-27(4)38(72-32(9)60)24-33-14-11-10-12-15-33)28(5)41(62)57-36(47(68)69)19-20-39(61)53-30(7)43(64)54-31(8)44(65)58-37/h10-12,14-15,17-18,23,25,27-29,31,34-38,40H,7,13,16,19-22,24H2,1-6,8-9H3,(H,53,61)(H,54,64)(H,55,66)(H,56,63)(H,57,62)(H,58,65)(H,59,67)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,26-23+/t27-,28-,29-,31+,34-,35-,36+,37-,38-,40+/m0/s1",OXEWVIJLTMFSCK-RJPWZEGISA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-isobutyl-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684726,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1874,"[D‐Asp3,ADMAdda5,Dha7]MC‐HilR",,,Microcystin,C49H72N10O13,1009.16,1008.528033,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](C[C@@H](C)CC)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C49H72N10O13/c1-9-26(2)23-37-46(67)59-38(48(70)71)25-41(62)55-35(16-13-21-52-49(50)51)45(66)56-34(18-17-27(3)22-28(4)39(72-32(8)60)24-33-14-11-10-12-15-33)29(5)42(63)57-36(47(68)69)19-20-40(61)53-30(6)43(64)54-31(7)44(65)58-37/h10-12,14-15,17-18,22,26,28-29,31,34-39H,6,9,13,16,19-21,23-25H2,1-5,7-8H3,(H,53,61)(H,54,64)(H,55,62)(H,56,66)(H,57,63)(H,58,65)(H,59,67)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,27-22+/t26-,28-,29-,31+,34-,35-,36+,37-,38+,39-/m0/s1",DYVNDYGAKNUGLZ-PVSWEASFSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-5,19-dimethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684727,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1875,"[Gly1,D-Asp3,ADMAdda5,(E/Z)-Dhb7]MC-LHar",,,Microcystin,C49H72N10O13,1009.16,1008.528033,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)C(=CC)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)CCCCNC(=N)N,"InChI=1S/C49H72N10O13/c1-8-33-44(65)53-26-42(63)56-37(22-27(2)3)46(67)59-38(48(70)71)25-41(62)55-35(16-12-13-21-52-49(50)51)45(66)57-34(30(6)43(64)58-36(47(68)69)19-20-40(61)54-33)18-17-28(4)23-29(5)39(72-31(7)60)24-32-14-10-9-11-15-32/h8-11,14-15,17-18,23,27,29-30,34-39H,12-13,16,19-22,24-26H2,1-7H3,(H,53,65)(H,54,61)(H,55,62)(H,56,63)(H,57,66)(H,58,64)(H,59,67)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,28-23+,33-8?/t29-,30-,34-,35-,36+,37-,38+,39-/m0/s1",YDRTZHHACZYGHJ-RCJRYNDHSA-N,"(8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-2-ethylidene-15-(4-guanidinobutyl)-8-isobutyl-19-methyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802437,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)","Detected in two hydro-terrestrial cyanobacterial mat samples collected from Miers Valley in the McMurdo Dry Valleys, Antarctica. Stereochemistry partially defined by advanced Marfey amino acid analysis. Undefined E/Z isomerism at Dhb."
CyanoMetDB_1876,"[D-Asp3,ADMAdda5,(E/Z)-Dhb7]MC‐LR",,,Microcystin,C49H72N10O13,1009.16,1008.528033,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C49H72N10O13/c1-9-33-44(65)53-30(7)43(64)58-37(22-26(2)3)46(67)59-38(48(70)71)25-41(62)55-35(16-13-21-52-49(50)51)45(66)56-34(29(6)42(63)57-36(47(68)69)19-20-40(61)54-33)18-17-27(4)23-28(5)39(72-31(8)60)24-32-14-11-10-12-15-32/h9-12,14-15,17-18,23,26,28-30,34-39H,13,16,19-22,24-25H2,1-8H3,(H,53,65)(H,54,61)(H,55,62)(H,56,66)(H,57,63)(H,58,64)(H,59,67)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,27-23+,33-9?/t28-,29-,30+,34-,35-,36+,37-,38+,39-/m0/s1",LTHMLXBUIQLYAJ-HUBHJHLRSA-N,"(5R,8S,11R,15S,18S,19S,22R,Z)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-2-ethylidene-15-(3-guanidinopropyl)-8-isobutyl-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",139585968,,10.1016/S0031-9422(97)00769-3,https://linkinghub.elsevier.com/retrieve/pii/S0031942297007693,"Three dehydrobutyrine-containing microcystins from Nostoc;Phytochemistry;47;7;;1998;journalArticle;10.1016/S0031-9422(97)00769-3;Beattie, Kenneth A.; Kaya, Kunimitsu; Sano, Tomoharu; Codd, Geoffrey A.",Nostoc,sp.,[Nostoc sp.]DUN901,,"Chirality of Dhb undefined, but all other amino acid chiralities assigned by NMR and chiral GC-MS analyses."
CyanoMetDB_1877,[D-MeO-Glu6]MC-LR,[D-Glu(OMe)6]MC-LR,,Microcystin,C50H76N10O12,1009.2,1008.564418,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)OC)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H76N10O12/c1-27(2)24-38-47(67)59-41(48(68)69)31(6)43(63)56-36(18-15-23-53-50(51)52)46(66)55-35(20-19-28(3)25-29(4)39(71-10)26-34-16-13-12-14-17-34)30(5)42(62)57-37(49(70)72-11)21-22-40(61)60(9)33(8)45(65)54-32(7)44(64)58-38/h12-14,16-17,19-20,25,27,29-32,35-39,41H,8,15,18,21-24,26H2,1-7,9-11H3,(H,54,65)(H,55,66)(H,56,63)(H,57,62)(H,58,64)(H,59,67)(H,68,69)(H4,51,52,53)/b20-19+,28-25+/t29-,30-,31-,32+,35-,36-,37+,38-,39-,41+/m0/s1",PONFOSATPJORFV-AFQNMZSJSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",101643573,,10.1016/0041-0101(92)90522-7,https://linkinghub.elsevier.com/retrieve/pii/0041010192905227,"Two methyl ester derivatives of microcystins, cyclic heptapeptide hepatotoxins, isolated from Anabaena flos-aquae strain CYA 83/1;Toxicon;30;11;;1992;journalArticle;10.1016/0041-0101(92)90522-7;Sivonen, Kaarina; Skulberg, Olav M.; Namikoshi, Michio; Evans, William R.; Carmichael, Wayne W.; Rinehart, Kenneth L.",Anabaena/Dolichospermum,flos aquae,CYA 83/1,,"Structure determined using FAB-MS(/MS) and Waters Pico-Tag amino acid analyzer, without NMR determination."
CyanoMetDB_1878,[Mdhb7]MC-LR,,,Microcystin,C50H76N10O12,1009.2,1008.564418,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)C(=CC)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)CC(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H76N10O12/c1-11-38-47(67)54-32(8)44(64)58-37(24-27(2)3)46(66)59-41(49(70)71)31(7)43(63)56-35(18-15-23-53-50(51)52)45(65)55-34(30(6)42(62)57-36(48(68)69)21-22-40(61)60(38)9)20-19-28(4)25-29(5)39(72-10)26-33-16-13-12-14-17-33/h11-14,16-17,19-20,25,27,29-32,34-37,39,41H,15,18,21-24,26H2,1-10H3,(H,54,67)(H,55,65)(H,56,63)(H,57,62)(H,58,64)(H,59,66)(H,68,69)(H,70,71)(H4,51,52,53)/b20-19+,28-25+,38-11?/t29-,30-,31-,32+,34-,35-,36+,37-,39-,41+/m0/s1",ZKRLHZKOFKCNKD-BNILPYKLSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-ethylidene-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684878,,10.1128/AEM.56.9.2650-2657.1990,https://AEM.asm.org/content/56/9/2650,"Isolation and characterization of hepatotoxic microcystin homologs from the filamentous freshwater cyanobacterium Nostoc sp. strain 152.;Applied and Environmental Microbiology;56;9;;1990;journalArticle;10.1128/AEM.56.9.2650-2657.1990;Sivonen, K; Carmichael, W W; Namikoshi, M; Rinehart, K L; Dahlem, A M; Niemelä, S I",Nostoc,sp.,[Nostoc sp.]152,,"Stereochemistry defined through chiral amino acid analyses, except for Dhb moiety where E/Z was not specified in article. The presence of Mdhb, instead of the usual Mdha, is based on amino acid and MS analyses only (NMR yet to be acquired)."
CyanoMetDB_1879,MC-HilR,,,Microcystin,C50H76N10O12,1009.2,1008.564418,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C[C@@H](C)CC)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H76N10O12/c1-11-27(2)25-38-47(67)59-41(49(70)71)31(6)43(63)56-36(18-15-23-53-50(51)52)46(66)55-35(20-19-28(3)24-29(4)39(72-10)26-34-16-13-12-14-17-34)30(5)42(62)57-37(48(68)69)21-22-40(61)60(9)33(8)45(65)54-32(7)44(64)58-38/h12-14,16-17,19-20,24,27,29-32,35-39,41H,8,11,15,18,21-23,25-26H2,1-7,9-10H3,(H,54,65)(H,55,66)(H,56,63)(H,57,62)(H,58,64)(H,59,67)(H,68,69)(H,70,71)(H4,51,52,53)/b20-19+,28-24+/t27-,29-,30-,31-,32+,35-,36-,37+,38-,39-,41+/m0/s1",PJPFCNPJHGMQBK-GHDNJWGDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",10486193,,10.1021/jo00117a017,https://pubs.acs.org/doi/abs/10.1021/jo00117a017,"Seven More Microcystins from Homer Lake Cells: Application of the General Method for Structure Assignment of Peptides Containing .alpha.,.beta.-Dehydroamino Acid Unit(s);The Journal of Organic Chemistry;60;12;;1995;journalArticle;10.1021/jo00117a017;Namikoshi, Michio; Sun, Furong; Choi, Byoung Wook; Rinehart, Kenneth L.; Carmichael, Wayne W.; Evans, William R.; Beasley, Val R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii,Detected in field samples from Homer Lake (Illinois) (M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii)
CyanoMetDB_1880,MC-LHar,,Microcystin HilR,Microcystin,C50H76N10O12,1009.2,1008.564418,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H76N10O12/c1-27(2)24-38-47(67)59-41(49(70)71)31(6)43(63)56-36(18-14-15-23-53-50(51)52)46(66)55-35(20-19-28(3)25-29(4)39(72-10)26-34-16-12-11-13-17-34)30(5)42(62)57-37(48(68)69)21-22-40(61)60(9)33(8)45(65)54-32(7)44(64)58-38/h11-13,16-17,19-20,25,27,29-32,35-39,41H,8,14-15,18,21-24,26H2,1-7,9-10H3,(H,54,65)(H,55,66)(H,56,63)(H,57,62)(H,58,64)(H,59,67)(H,68,69)(H,70,71)(H4,51,52,53)/b20-19+,28-25+/t29-,30-,31-,32+,35-,36-,37+,38-,39-,41+/m0/s1",HMGQXYULLUEIPT-AFQNMZSJSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-8-isobutyl-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683854,DTXSID601016185,10.1016/S0041-0101(00)00105-7,https://linkinghub.elsevier.com/retrieve/pii/S0041010100001057,"Isolation and characterization of microcystins from a River Nile strain of Oscillatoria tenuis Agardh ex Gomont;Toxicon;38;12;;2000;journalArticle;10.1016/S0041-0101(00)00105-7;Brittain, S.; Mohamed, Z.A.; Wang, J.; Lehmann, V.K.B.; Carmichael, W.W.; Rinehart, K.L.",Oscillatoria,tenuis,[Oscillatoria tenuis]E6,,Extensively characterised by complementary techniques.
CyanoMetDB_1881,[Me-Ala1]MC‐LR ,"[Me-Leu2]MC‐LR, probably MC-HilR!",,Microcystin,C50H76N10O12,1009.2,1008.564418,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)C[C@H](CC)C)=O)=O)=O)=O,"InChI=1S/C50H76N10O12/c1-11-27(2)25-38-47(67)59-41(49(70)71)31(6)43(63)56-36(18-15-23-53-50(51)52)46(66)55-35(20-19-28(3)24-29(4)39(72-10)26-34-16-13-12-14-17-34)30(5)42(62)57-37(48(68)69)21-22-40(61)60(9)33(8)45(65)54-32(7)44(64)58-38/h12-14,16-17,19-20,24,27,29-32,35-39,41H,8,11,15,18,21-23,25-26H2,1-7,9-10H3,(H,54,65)(H,55,66)(H,56,63)(H,57,62)(H,58,64)(H,59,67)(H,68,69)(H,70,71)(H4,51,52,53)/b20-19+,28-24+/t27-,29-,30-,31-,32+,35-,36-,37+,38-,39-,41+/m0/s1",PJPFCNPJHGMQBK-GHDNJWGDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",10486193,,10.1038/ja.2006.95,http://www.nature.com/articles/ja200695,"Structural Characterization of Microcystins by LC/MS/MS under Ion Trap Conditions;The Journal of Antibiotics;59;11;;2006;journalArticle;10.1038/ja.2006.95;Mayumi, Tsuyoshi; Kato, Hajime; Imanishi, Susumu; Kawasaki, Yoshito; Hasegawa, Masateru; Harada, Ken-ichi",n.a.,n.a.,n.a.,"field sample, surface bloom collected from Lake Suwa, Japan","Cited article reports molecules as containing either methylated Ala (position 1) or methylate Leu (position 2) as the constituent amino acid. Structure is assumed based on other MC congeners and is given here as MC-HilR (on account of methylate alanine in position 1 not being widely reported in other articles).
MS2 data available in the article. "
CyanoMetDB_1882,"[D-Leu1,D-Asp³,DMAdda5]MC‐LR",,Microcystin HilR,Microcystin,C50H76N10O12,1009.2,1008.564418,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C50H76N10O12/c1-27(2)22-37-46(67)58-38(23-28(3)4)47(68)59-39(49(71)72)26-41(62)54-35(16-13-21-53-50(51)52)45(66)55-34(18-17-29(5)24-30(6)40(61)25-33-14-11-10-12-15-33)31(7)43(64)56-36(48(69)70)19-20-42(63)60(9)32(8)44(65)57-37/h10-12,14-15,17-18,24,27-28,30-31,34-40,61H,8,13,16,19-23,25-26H2,1-7,9H3,(H,54,62)(H,55,66)(H,56,64)(H,57,65)(H,58,67)(H,59,68)(H,69,70)(H,71,72)(H4,51,52,53)/b18-17+,29-24+/t30-,31-,34-,35-,36+,37+,38-,39+,40-/m0/s1",KIYYTZXXJAGYEI-AGNPPKSKSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,8-diisobutyl-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802159,DTXSID601016185,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,"Stereochemistry assumed based on other MC congeners. Compound is bioaccumulated in lichen. Detected in Peltigera degenii (lichen species). Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_1883,"[Gly1,D-Asp3]MC-RR",,,Microcystin,C47H71N13O12,1010.15,1009.53451,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H71N13O12/c1-26(22-27(2)36(72-6)23-30-12-8-7-9-13-30)16-17-31-28(3)40(64)58-34(44(68)69)18-19-39(63)60(5)29(4)41(65)54-25-38(62)56-33(15-11-21-53-47(50)51)43(67)59-35(45(70)71)24-37(61)55-32(42(66)57-31)14-10-20-52-46(48)49/h7-9,12-13,16-17,22,27-28,31-36H,4,10-11,14-15,18-21,23-25H2,1-3,5-6H3,(H,54,65)(H,55,61)(H,56,62)(H,57,66)(H,58,64)(H,59,67)(H,68,69)(H,70,71)(H4,48,49,52)(H4,50,51,53)/b17-16+,26-22+/t27-,28-,31-,32-,33-,34+,35+,36-/m0/s1",XZTWPWTUTORJDG-XDZREONBSA-N,"(8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683836,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",n.a.,n.a.,n.a.,"field samples, from various benthic mats",From Antarctica. Compound MC-2 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1884,"[D-Asp3,Dha7]MC-RR",,,Microcystin,C47H71N13O12,1010.15,1009.534515,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H71N13O12/c1-25(22-26(2)36(72-6)23-30-12-8-7-9-13-30)16-17-31-27(3)39(63)59-34(44(68)69)18-19-37(61)54-28(4)40(64)55-29(5)41(65)58-33(15-11-21-53-47(50)51)43(67)60-35(45(70)71)24-38(62)56-32(42(66)57-31)14-10-20-52-46(48)49/h7-9,12-13,16-17,22,26-27,29,31-36H,4,10-11,14-15,18-21,23-24H2,1-3,5-6H3,(H,54,61)(H,55,64)(H,56,62)(H,57,66)(H,58,65)(H,59,63)(H,60,67)(H,68,69)(H,70,71)(H4,48,49,52)(H4,50,51,53)/b17-16+,25-22+/t26-,27-,29+,31-,32-,33-,34+,35+,36-/m0/s1",UWKDRDKCWDBPNK-WXJJDZFKSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6449930,,10.1073/pnas.86.3.770,http://www.pnas.org/cgi/doi/10.1073/pnas.86.3.770,"Structural characterization of toxic cyclic peptides from blue-green algae by tandem mass spectrometry.;Proceedings of the National Academy of Sciences;86;3;;1989;journalArticle;10.1073/pnas.86.3.770;Krishnamurthy, T.; Szafraniec, L.; Hunt, D. F.; Shabanowitz, J.; Yates, J. R.; Hauer, C. R.; Carmichael, W. W.; Skulberg, O.; Codd, G. A.; Missler, S.",Microcystis,aeruginosa,n.a.,,"Stereochemistry based on chemical derivatisation of amino acids hydrolysed from parent compound. Reported in M. aeruginosa strain isolated from Akersvatn, Norway, August 1984."
CyanoMetDB_1885,"[D-Asp³,DMAdda5]MC‐RR",,,Microcystin,C47H71N13O12,1010.15,1009.534515,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C47H71N13O12/c1-25(22-26(2)36(61)23-30-12-8-7-9-13-30)16-17-31-27(3)39(64)58-34(44(69)70)18-19-38(63)60(6)29(5)41(66)54-28(4)40(65)57-33(15-11-21-53-47(50)51)43(68)59-35(45(71)72)24-37(62)55-32(42(67)56-31)14-10-20-52-46(48)49/h7-9,12-13,16-17,22,26-28,31-36,61H,5,10-11,14-15,18-21,23-24H2,1-4,6H3,(H,54,66)(H,55,62)(H,56,67)(H,57,65)(H,58,64)(H,59,68)(H,69,70)(H,71,72)(H4,48,49,52)(H4,50,51,53)/b17-16+,25-22+/t26-,27-,28+,31-,32-,33-,34+,35+,36-/m0/s1",SZNUVOZIIWMKCN-KSLDGVDMSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684701,,10.1128/Jb.185.2.564-572.2003,http://jb.asm.org/cgi/doi/10.1128/JB.185.2.564-572.2003,"Microcystin Biosynthesis in Planktothrix: Genes, Evolution, and Manipulation;Journal of Bacteriology;185;2;;2003;journalArticle;10.1128/JB.185.2.564-572.2003;Christiansen, G.; Fastner, J.; Erhard, M.; Borner, T.; Dittmann, E.",Oscillatoria/Planktothrix,agardhii,[Oscillatoria/Planktothrix]CYA126/8,,Stereochemistry assumed based on other MC congeners. Location of demethylation on Adda moiety is assumed to be at the methoxy group - cited reference reported DMAdda but does not present the raw data.
CyanoMetDB_1886,"[Gly1,D-Asp3,Dhb7]MC-RR",,,Microcystin,C47H71N13O12,1010.15,1009.534515,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)C(=CC)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)CCCNC(=N)N)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H71N13O12/c1-6-30-41(65)54-25-39(63)57-33(15-11-21-53-47(50)51)43(67)60-35(45(70)71)24-38(62)56-32(14-10-20-52-46(48)49)42(66)58-31(28(4)40(64)59-34(44(68)69)18-19-37(61)55-30)17-16-26(2)22-27(3)36(72-5)23-29-12-8-7-9-13-29/h6-9,12-13,16-17,22,27-28,31-36H,10-11,14-15,18-21,23-25H2,1-5H3,(H,54,65)(H,55,61)(H,56,62)(H,57,63)(H,58,66)(H,59,64)(H,60,67)(H,68,69)(H,70,71)(H4,48,49,52)(H4,50,51,53)/b17-16+,26-22+,30-6?/t27-,28-,31-,32-,33-,34+,35+,36-/m0/s1",KRUAITXTWMLKOY-AGFRCYLPSA-N,"(8S,11R,15S,18S,19S,22R)-2-ethylidene-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-19-methyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683803,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)","Detected in two hydro-terrestrial cyanobacterial mat samples collected from Miers Valley in the McMurdo Dry Valleys, Antarctica. Stereochemistry partially defined by advanced Marfey amino acid analysis. Undefined E/Z isomerism at Dhb."
CyanoMetDB_1887,MC-ER,,,Microcystin,C48H70N10O14,1011.13,1010.507297,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC(O)=O)=O)=O)=O)=O,"InChI=1S/C48H70N10O14/c1-25(23-26(2)36(72-8)24-31-13-10-9-11-14-31)16-17-32-27(3)40(62)56-35(46(68)69)18-20-37(59)58(7)30(6)43(65)52-29(5)42(64)55-34(19-21-38(60)61)45(67)57-39(47(70)71)28(4)41(63)54-33(44(66)53-32)15-12-22-51-48(49)50/h9-11,13-14,16-17,23,26-29,32-36,39H,6,12,15,18-22,24H2,1-5,7-8H3,(H,52,65)(H,53,66)(H,54,63)(H,55,64)(H,56,62)(H,57,67)(H,60,61)(H,68,69)(H,70,71)(H4,49,50,51)/b17-16+,25-23+/t26-,27-,28-,29+,32-,33-,34-,35+,36-,39+/m0/s1",ONKWEJXQUSPSTI-CGABAVKJSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(2-carboxyethyl)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684955,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,"AB2017/14, AB2017/15",,
CyanoMetDB_1888,[D-Asp3]MC-LW,,,Microcystin,C53H70N8O12,1011.17,1010.51132,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C53H70N8O12/c1-29(2)23-41-50(67)60-43(53(71)72)27-45(62)56-42(26-36-28-54-39-18-14-13-17-37(36)39)51(68)57-38(20-19-30(3)24-31(4)44(73-9)25-35-15-11-10-12-16-35)32(5)47(64)58-40(52(69)70)21-22-46(63)61(8)34(7)49(66)55-33(6)48(65)59-41/h10-20,24,28-29,31-33,38,40-44,54H,7,21-23,25-27H2,1-6,8-9H3,(H,55,66)(H,56,62)(H,57,68)(H,58,64)(H,59,65)(H,60,67)(H,69,70)(H,71,72)/b20-19+,30-24+/t31-,32-,33+,38-,40+,41-,42-,43+,44-/m0/s1",KEUIEPSPMZCRNU-MGDFNBQSSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(indolin-3-ylmethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802154,,10.1021/es991294v,https://pubs.acs.org/doi/10.1021/es991294v,"Hepatotoxin Production Kinetics of the Cyanobacterium Microcystis aeruginosa PCC 7820, as Determined by HPLC−Mass Spectrometry and Protein Phosphatase Bioassay;Environmental Science & Technology;34;16;;2000;journalArticle;10.1021/es991294v;Robillot, Cédric; Vinh, JoËlle; Puiseux-Dao, Simone; Hennion, Marie-Claire",Microcystis,aeruginosa,[Microcystis aeruginosa]PCC7820,,Stereochemistry assumed based on other MC congeners (no amino acid chirality checks or 2D-NMR performed).
CyanoMetDB_1889,"[D-Asp3,(E)-Dhb7]MC-LW","[D-Asp3,(E)-Dhb7]MC-LW",,Microcystin,C53H70N8O12,1011.17,1010.51132,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C\C)/NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C53H70N8O12/c1-9-37-49(66)55-33(7)48(65)60-41(23-29(2)3)50(67)61-43(53(71)72)27-46(63)57-42(26-35-28-54-39-18-14-13-17-36(35)39)51(68)58-38(32(6)47(64)59-40(52(69)70)21-22-45(62)56-37)20-19-30(4)24-31(5)44(73-8)25-34-15-11-10-12-16-34/h9-20,24,28-29,31-33,38,40-44,54H,21-23,25-27H2,1-8H3,(H,55,66)(H,56,62)(H,57,63)(H,58,68)(H,59,64)(H,60,65)(H,61,67)(H,69,70)(H,71,72)/b20-19+,30-24+,37-9+/t31-,32-,33+,38-,40+,41-,42-,43+,44-/m0/s1",MPMAWWUGDHJXMB-GJVNGLMXSA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-15-(indolin-3-ylmethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684777,,10.1007/s13659-013-0001-3,http://link.springer.com/10.1007/s13659-013-0001-3,"Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80;Natural Products and Bioprospecting;4;1;;2014;journalArticle;10.1007/s13659-013-0001-3;Niedermeyer, Timo H. J.; Schmieder, Peter; Kurmayer, Rainer",Oscillatoria/Planktothrix,rubescens,80,,"Stereochemistry assumed based on relative MC congeners, synthesised by the same synthetase enzyme."
CyanoMetDB_1890,[epoxyAdda5]MC-LR,,,Microcystin,C49H74N10O13,1011.17,1010.543682,O=C(O)[C@@H]1NC(=O)[C@@H](C)[C@H](/C=C/C2(C)OC2[C@H](C)[C@@H](OC)Cc2ccccc2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC1)C(=O)O,"InChI=1S/C49H74N10O13/c1-25(2)23-35-45(66)58-38(47(69)70)28(5)41(62)55-33(17-14-22-52-48(50)51)44(65)54-32(20-21-49(8)39(72-49)27(4)36(71-10)24-31-15-12-11-13-16-31)26(3)40(61)56-34(46(67)68)18-19-37(60)59(9)30(7)43(64)53-29(6)42(63)57-35/h11-13,15-16,20-21,25-29,32-36,38-39H,7,14,17-19,22-24H2,1-6,8-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b21-20+/t26-,27+,28-,29+,32-,33-,34+,35-,36-,38+,39?,49?/m0/s1",ULEIGMUDFOUZQL-MGVLZLMXSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((E)-2-(3-((2R,3S)-3-methoxy-4-phenylbutan-2-yl)-2-methyloxiran-2-yl)vinyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683856,,10.1016/j.toxicon.2019.06.006,https://linkinghub.elsevier.com/retrieve/pii/S0041010119301795,"Comprehensive multi-technique approach reveals the high diversity of microcystins in field collections and an associated isolate of Microcystis aeruginosa from a Turkish lake;Toxicon;167;;;2019;journalArticle;10.1016/j.toxicon.2019.06.006;Yilmaz, Mete; Foss, Amanda J.; Miles, Christopher O.; Özen, Mihriban; Demir, Nilsun; Balcı, Muharrem; Beach, Daniel G.",n.a.,n.a.,n.a.,"field samples, Lake Uluabat, Turkey","Detected in complex lake extract comprising multiple species, with Dolichospermum spiroides, Planktothrix isothrix and Microcystis aeruginosa dominating (in order of estimated biovolumes). Putative annotation - structure currently based only on LC-HRMS and the compounds derivatization with two molecules of mercaptoethanol (at Mdha and the epoxide). Hence, InChI and SMILES are for an epoxy group at an arbitrarily chosen double bond in the Adda group."
CyanoMetDB_1891,MC‐OiaAba,"MC‐OiaAbu (oxidised W), MC-oxindolylalanine-aminobutanoic acid",,Microcystin,C52H68N8O13,1013.14,1012.490585,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC2c3ccccc3NC2=O)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H68N8O13/c1-10-36-49(67)55-37(21-20-27(2)24-28(3)41(73-9)25-33-16-12-11-13-17-33)29(4)44(62)57-39(51(69)70)22-23-42(61)60(8)32(7)47(65)53-31(6)46(64)58-40(26-35-34-18-14-15-19-38(34)56-48(35)66)50(68)59-43(52(71)72)30(5)45(63)54-36/h11-21,24,28-31,35-37,39-41,43H,7,10,22-23,25-26H2,1-6,8-9H3,(H,53,65)(H,54,63)(H,55,67)(H,56,66)(H,57,62)(H,58,64)(H,59,68)(H,69,70)(H,71,72)/b21-20+,27-24+/t28-,29-,30-,31+,35?,36-,37-,39+,40-,41-,43+/m0/s1",RMLFSXGWVPECCA-NNOGGRAWSA-N,"15-ethyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-((2-oxoindolin-3-yl)methyl)-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683824,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Structure is putative and based on LC-MS/MS (unit res.) and HR-ESI-MS analysis. Stereochemistry assumed relative to MC-NfkA
CyanoMetDB_1892,MC-MR,,,Microcystin,C48H72N10O12S,1013.21,1012.505189,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12S/c1-26(24-27(2)37(70-8)25-32-14-11-10-12-15-32)17-18-33-28(3)40(60)56-36(46(66)67)19-20-38(59)58(7)31(6)43(63)52-30(5)42(62)55-35(21-23-71-9)45(65)57-39(47(68)69)29(4)41(61)54-34(44(64)53-33)16-13-22-51-48(49)50/h10-12,14-15,17-18,24,27-30,33-37,39H,6,13,16,19-23,25H2,1-5,7-9H3,(H,52,63)(H,53,64)(H,54,61)(H,55,62)(H,56,60)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,26-24+/t27-,28-,29-,30+,33-,34-,35-,36+,37-,39+/m0/s1",IZYCTPOMKJTWJD-MCUDKQGFSA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-8-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684782,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,"Thiol derivatization of Mdha, S-oxidation to MC-M(O)R"
CyanoMetDB_1893,"[D-Asp3,Mser7]MC‐LR","[D-Asp3, L-NMe-Ser7]MC‐LR",,Microcystin,C48H74N10O13,999.16,998.5436828,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](CO)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)CC(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H74N10O13/c1-26(2)21-35-44(65)57-36(47(69)70)24-39(60)53-33(15-12-20-51-48(49)50)43(64)54-32(17-16-27(3)22-28(4)38(71-8)23-31-13-10-9-11-14-31)29(5)41(62)55-34(46(67)68)18-19-40(61)58(7)37(25-59)45(66)52-30(6)42(63)56-35/h9-11,13-14,16-17,22,26,28-30,32-38,59H,12,15,18-21,23-25H2,1-8H3,(H,52,66)(H,53,60)(H,54,64)(H,55,62)(H,56,63)(H,57,65)(H,67,68)(H,69,70)(H4,49,50,51)/b17-16+,27-22+/t28-,29-,30+,32-,33-,34+,35-,36+,37-,38-/m0/s1",HBXZQNYNISTYMB-PRSKPVKISA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684704,,10.1007/s00203-004-0711-3,http://link.springer.com/10.1007/s00203-004-0711-3,"Diversity of coexisting Planktothrix (Cyanobacteria) chemotypes deduced by mass spectral analysis of microystins and other oligopeptides;Archives of Microbiology;182;4;;2004;journalArticle;10.1007/s00203-004-0711-3;Welker, Martin; Christiansen, Guntram; von Döhren, Hans",Planktothrix; Dolichospermum/Anabaena,[Planktothrix]sp.; [Dolicospermum]sp.,[Planktothrix sp.]Max06;[Dolicospermum sp.]NIVA-CYA 656,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1894,MC-LA,,,Microcystin,C46H67N7O12,910.06,909.4847709,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C46H67N7O12/c1-24(2)21-35-44(60)52-38(46(63)64)28(6)40(56)47-29(7)41(57)49-33(18-17-25(3)22-26(4)36(65-11)23-32-15-13-12-14-16-32)27(5)39(55)50-34(45(61)62)19-20-37(54)53(10)31(9)43(59)48-30(8)42(58)51-35/h12-18,22,24,26-30,33-36,38H,9,19-21,23H2,1-8,10-11H3,(H,47,56)(H,48,59)(H,49,57)(H,50,55)(H,51,58)(H,52,60)(H,61,62)(H,63,64)/b18-17+,25-22+/t26-,27-,28-,29-,30+,33-,34+,35-,36-,38+/m0/s1",DIAQQISRBBDJIM-DRSCAGMXSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6437382,,10.1039/p19840002311,http://xlink.rsc.org/?DOI=p19840002311,"The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aeruginosa;Journal of the Chemical Society, Perkin Transactions 1;;;;1984;journalArticle;10.1039/p19840002311;Botes, Dawie P.; Tuinman, Albert A.; Wessels, Philippus L.; Viljoen, Cornelis C.; Kruger, Hel�ne; Williams, Dudley H.; Santikarn, Sitthivet; Smith, Richard J.; Hammond, Stephen J.",Microcystis,aeruginosa,B2666,,Stereochemistry determined using amino acid and indicative chemical analyses; [Botes 1984] Microcystis aeruginosa B2666
CyanoMetDB_1895,[D-Asp3]MC-RY,,,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C51H70N10O13/c1-28(24-29(2)41(74-7)26-33-12-9-8-10-13-33)15-20-36-30(3)44(65)59-38(49(70)71)21-22-43(64)61(6)32(5)46(67)55-31(4)45(66)58-37(14-11-23-54-51(52)53)47(68)60-40(50(72)73)27-42(63)56-39(48(69)57-36)25-34-16-18-35(62)19-17-34/h8-10,12-13,15-20,24,29-31,36-41,62H,5,11,14,21-23,25-27H2,1-4,6-7H3,(H,55,67)(H,56,63)(H,57,69)(H,58,66)(H,59,65)(H,60,68)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,28-24+/t29-,30-,31+,36-,37-,38+,39-,40+,41-/m0/s1",AKRUYPJUAZTDLQ-XAIZWMDNSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-(3-guanidinopropyl)-15-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801630,,10.1002/tox.20522,http://doi.wiley.com/10.1002/tox.20522,"Occurrence of microcystin-producing cyanobacteria in Ugandan freshwater habitats;Environmental Toxicology;25;4;;2009;journalArticle;10.1002/tox.20522;Okello, William; Portmann, Cyril; Erhard, Marcel; Gademann, Karl; Kurmayer, Rainer",Microcystis,aeruginosa,NIVA-CYA 548,,"Okello 2009 identified in Ugandan freshwater sample comprising M. aeruginosa. Primarily identified by LC-MS/MS and HRMS, but related MC-RY has been characterised in detail by 2D-NMR (Miles 2012) - enhanced confidence in [D-Asp3]MC-RY structure; [Okello 2009] [Microcystis]aeruginosa; [Miles 2012] [Microcystis]aeruginosa NIVA-CYA 548"
CyanoMetDB_1896,MC-NfkA,MC‐NfkA (oxidised W),,Microcystin,C51H66N8O14,1015.11,1014.469849,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](C)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C(C=CC=C3)=C3NC=O)=O)=O)=O)=O)=O,"InChI=1S/C51H66N8O14/c1-27(23-28(2)41(73-9)24-34-15-11-10-12-16-34)19-20-36-29(3)44(63)56-38(50(69)70)21-22-42(62)59(8)33(7)48(67)54-32(6)47(66)57-39(25-40(61)35-17-13-14-18-37(35)52-26-60)49(68)58-43(51(71)72)30(4)45(64)53-31(5)46(65)55-36/h10-20,23,26,28-32,36,38-39,41,43H,7,21-22,24-25H2,1-6,8-9H3,(H,52,60)(H,53,64)(H,54,67)(H,55,65)(H,56,63)(H,57,66)(H,58,68)(H,69,70)(H,71,72)/b20-19+,27-23+/t28-,29-,30-,31-,32+,36-,38+,39-,41-,43+/m0/s1",PLRHHYYFAQRVST-DJNDZUCYSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-3,6,9,13,16,20-hexahydroxy-8-(2-(2-((hydroxymethylene)amino)phenyl)-2-oxoethyl)-18-((1E,3Z,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid",155802270,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,,"Structure confirmed by, 1- and 2D-NMR, in addition to LC-MS/MS and HR-ESI-MS analyses."
CyanoMetDB_1897,[D-Asp³]MC‐M(O)R,[Asp3]MC‐M(O)R (oxidation artefact),,Microcystin,C47H70N10O13S,1015.18,1014.484453,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCS(C)=O)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O13S/c1-26(23-27(2)37(70-7)24-31-13-10-9-11-14-31)16-17-32-28(3)40(60)55-35(45(65)66)18-19-39(59)57(6)30(5)42(62)51-29(4)41(61)54-34(20-22-71(8)69)44(64)56-36(46(67)68)25-38(58)52-33(43(63)53-32)15-12-21-50-47(48)49/h9-11,13-14,16-17,23,27-29,32-37H,5,12,15,18-22,24-25H2,1-4,6-8H3,(H,51,62)(H,52,58)(H,53,63)(H,54,61)(H,55,60)(H,56,64)(H,65,66)(H,67,68)(H4,48,49,50)/b17-16+,26-23+/t27-,28-,29+,32-,33-,34-,35+,36+,37-,71?/m0/s1",OJRPYWXWCYXSKY-YJSIYZBQSA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-8-(2-(methylsulfinyl)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684783,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,Stereochemistry assumed based on other MC congeners. Stereochemistry at sulfoxide is recemic and therefore presented as a mixture of diastereoisomers. Thiol derivatization of Mdha & S-oxidation also used.
CyanoMetDB_1898,[D-Asp3]MC-FR,,,Microcystin,C51H70N10O12,1015.16,1014.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H70N10O12/c1-29(25-30(2)41(73-7)27-35-17-12-9-13-18-35)20-21-36-31(3)44(64)58-38(49(69)70)22-23-43(63)61(6)33(5)46(66)55-32(4)45(65)59-39(26-34-15-10-8-11-16-34)48(68)60-40(50(71)72)28-42(62)56-37(47(67)57-36)19-14-24-54-51(52)53/h8-13,15-18,20-21,25,30-32,36-41H,5,14,19,22-24,26-28H2,1-4,6-7H3,(H,55,66)(H,56,62)(H,57,67)(H,58,64)(H,59,65)(H,60,68)(H,69,70)(H,71,72)(H4,52,53,54)/b21-20+,29-25+/t30-,31-,32+,36-,37-,38+,39-,40+,41-/m0/s1",SLBUJXKVOVJXQZ-KUOJBGIXSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-benzyl-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802326,,N/A,https://ejournal.sinica.edu.tw/bbas/content/2000/3/bot13-04-info.html,,Microcystis,aeruginosa,[Microcystis aeruginosa]M.TN-2,,Stereochemistry defined through chiral amino acid analysis.
CyanoMetDB_1899,[Dha7]MC-FR,,,Microcystin,C51H70N10O12,1015.16,1014.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H70N10O12/c1-28(25-29(2)40(73-7)27-35-17-12-9-13-18-35)20-21-36-30(3)43(63)59-38(49(69)70)22-23-41(62)55-32(5)45(65)56-33(6)46(66)60-39(26-34-15-10-8-11-16-34)48(68)61-42(50(71)72)31(4)44(64)58-37(47(67)57-36)19-14-24-54-51(52)53/h8-13,15-18,20-21,25,29-31,33,36-40,42H,5,14,19,22-24,26-27H2,1-4,6-7H3,(H,55,62)(H,56,65)(H,57,67)(H,58,64)(H,59,63)(H,60,66)(H,61,68)(H,69,70)(H,71,72)(H4,52,53,54)/b21-20+,28-25+/t29-,30-,31-,33+,36-,37-,38+,39-,40-,42+/m0/s1",CKQUGBQJZGUNMT-PLADHRKZSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101659871,,10.1016/0041-0101(94)90030-2,https://linkinghub.elsevier.com/retrieve/pii/0041010194900302,"Isolation and identification of 12 microcystins from four strains and two bloom samples of Microcystis spp.: structure of a new hepatotoxin;Toxicon;32;1;;1994;journalArticle;10.1016/0041-0101(94)90030-2;Luukkainen, Raija; Namikoshi, Michio; Sivonen, Kaarina; Rinehart, Kenneth L.; Niemelä, Seppo I.",Microcystis,aeruginosa,[Microcystis aeruginosa]98,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1900,"[D‐Asp3,Dha7]MC‐HphR",,,Microcystin,C51H70N10O12,1015.16,1014.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H70N10O12/c1-29(26-30(2)41(73-6)27-35-16-11-8-12-17-35)19-21-36-31(3)44(64)60-39(49(69)70)23-24-42(62)55-32(4)45(65)56-33(5)46(66)59-38(22-20-34-14-9-7-10-15-34)48(68)61-40(50(71)72)28-43(63)57-37(47(67)58-36)18-13-25-54-51(52)53/h7-12,14-17,19,21,26,30-31,33,36-41H,4,13,18,20,22-25,27-28H2,1-3,5-6H3,(H,55,62)(H,56,65)(H,57,63)(H,58,67)(H,59,66)(H,60,64)(H,61,68)(H,69,70)(H,71,72)(H4,52,53,54)/b21-19+,29-26+/t30-,31-,33+,36-,37-,38-,39+,40+,41-/m0/s1",OAEKMBBQVHZUFO-YGMMJAELSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684728,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Anabaena,n.a.,[Anabaena sp.]66A,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1901,[DMAdda5]MC‐FR,,,Microcystin,C51H70N10O12,1015.16,1014.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C51H70N10O12/c1-28(25-29(2)40(62)27-35-17-12-9-13-18-35)20-21-36-30(3)43(64)58-38(49(70)71)22-23-41(63)61(7)33(6)46(67)55-32(5)45(66)59-39(26-34-15-10-8-11-16-34)48(69)60-42(50(72)73)31(4)44(65)57-37(47(68)56-36)19-14-24-54-51(52)53/h8-13,15-18,20-21,25,29-32,36-40,42,62H,6,14,19,22-24,26-27H2,1-5,7H3,(H,55,67)(H,56,68)(H,57,65)(H,58,64)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b21-20+,28-25+/t29-,30-,31-,32+,36-,37-,38+,39-,40-,42+/m0/s1",QOQCTPNZCVODIX-DXENUKDNSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684738,,10.1094/MPMI-22-6-0695,http://apsjournals.apsnet.org/doi/10.1094/MPMI-22-6-0695,"Microcystin Production in the Tripartite Cyanolichen Peltigera leucophlebia;Molecular Plant-Microbe Interactions;22;6;;2009;journalArticle;10.1094/MPMI-22-6-0695;Kaasalainen, Ulla; Jokela, Jouni; Fewer, David P.; Sivonen, Kaarina; Rikkinen, Jouko",Nostoc,sp.,[Nostoc sp.]UK18,,Stereochemistry inferred based on other MC congeners.
CyanoMetDB_1902,[D-Asp³]MC‐RF,,,Microcystin,C51H70N10O12,1015.16,1014.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H70N10O12/c1-29(25-30(2)41(73-7)27-35-17-12-9-13-18-35)20-21-36-31(3)44(64)59-38(49(69)70)22-23-43(63)61(6)33(5)46(66)55-32(4)45(65)58-37(19-14-24-54-51(52)53)47(67)60-40(50(71)72)28-42(62)56-39(48(68)57-36)26-34-15-10-8-11-16-34/h8-13,15-18,20-21,25,30-32,36-41H,5,14,19,22-24,26-28H2,1-4,6-7H3,(H,55,66)(H,56,62)(H,57,68)(H,58,65)(H,59,64)(H,60,67)(H,69,70)(H,71,72)(H4,52,53,54)/b21-20+,29-25+/t30-,31-,32+,36-,37-,38+,39-,40+,41-/m0/s1",JVGZZTIFWWWSIC-KUOJBGIXSA-N,"15-benzyl-8-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802143,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,[Microcystis aeruginosa]CYA548,,Stereochemistry assumed based on other MC congeners. Thiol derivatization of Mdha
CyanoMetDB_1903,[L-Ser7]MC-E(OMe)E(OMe),,,Microcystin,C48H69N7O17,1016.1,1015.474994,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](C)NC(=O)[C@H](CO)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H69N7O17/c1-25(22-26(2)36(70-6)23-30-12-10-9-11-13-30)14-15-31-27(3)41(60)54-34(47(66)67)16-19-37(57)50-35(24-56)46(65)49-29(5)43(62)53-33(18-21-39(59)72-8)45(64)55-40(48(68)69)28(4)42(61)52-32(44(63)51-31)17-20-38(58)71-7/h9-15,22,26-29,31-36,40,56H,16-21,23-24H2,1-8H3,(H,49,65)(H,50,57)(H,51,63)(H,52,61)(H,53,62)(H,54,60)(H,55,64)(H,66,67)(H,68,69)/b15-14+,25-22+/t26-,27-,28-,29+,31-,32-,33-,34+,35-,36-,40+/m0/s1",AMOBUNZQEUJLCJ-WBINVAHYSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8,15-bis(3-methoxy-3-oxopropyl)-5,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683848,,10.1021/tx970120t,https://pubs.acs.org/doi/10.1021/tx970120t,"Seven New Microcystins Possessing Two Glutamic Acid Units Isolated from Anabaena sp. Strain 186;Chemical Research in Toxicology;11;2;;1998;journalArticle;10.1021/tx970120t;Namikoshi, Michio; Yuan, Moucun; Sivonen, Kaarina; Carmichael, Wayne W.; Rinehart, Kenneth L.; Rouhiainen, Leo; Sun, Furong; Brittain, Scott; Otsuki, Akira",Anabaena,n.a.,[Anabaena sp.]186,,"Chirality thoroughly evaluated using Waters Pico-Tag / chiral GC amino acid analysis. Compound #3 in ref. Chiral GC-MS and/or Waters Pico-Tag analyser used for amino acid analysis, therefore, assume amino acid L/D forms are correct. FAB-MS and ESI-MS, both with CID-based MS/MS. No NMR used for assignment of the glutamates. Assignment of E(OMe)E(OMe) was justified as: ""Since only the methyl ester among the above derivatives can give glutamic acid by the acid hydrolysis used for amino acid analysis, the two L-amino acid units were assigned as the methyl ester derivative of Glu""."
CyanoMetDB_1904,MC‐LHty,,,Microcystin,C53H73N7O13,1016.19,1015.526636,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCc2ccc(O)cc2)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C53H73N7O13/c1-29(2)26-42-51(68)59-45(53(71)72)33(6)47(64)56-40(23-19-36-17-20-38(61)21-18-36)50(67)55-39(22-16-30(3)27-31(4)43(73-10)28-37-14-12-11-13-15-37)32(5)46(63)57-41(52(69)70)24-25-44(62)60(9)35(8)49(66)54-34(7)48(65)58-42/h11-18,20-22,27,29,31-34,39-43,45,61H,8,19,23-26,28H2,1-7,9-10H3,(H,54,66)(H,55,67)(H,56,64)(H,57,63)(H,58,65)(H,59,68)(H,69,70)(H,71,72)/b22-16+,30-27+/t31-,32-,33-,34+,39-,40-,41+,42-,43-,45+/m0/s1",DBXKFHRYAHVEAX-NCUDYEQPSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(4-hydroxyphenethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684774,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Phormidium,sp.,[Phormidium sp.]DVL1003c,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1905,"[D-Asp³,Dha7]MC‐RY",,,Microcystin,C50H68N10O13,1017.13,1016.496733,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H68N10O13/c1-27(23-28(2)40(73-6)25-32-11-8-7-9-12-32)14-19-35-29(3)43(64)59-37(48(69)70)20-21-41(62)54-30(4)44(65)55-31(5)45(66)58-36(13-10-22-53-50(51)52)46(67)60-39(49(71)72)26-42(63)56-38(47(68)57-35)24-33-15-17-34(61)18-16-33/h7-9,11-12,14-19,23,28-29,31,35-40,61H,4,10,13,20-22,24-26H2,1-3,5-6H3,(H,54,62)(H,55,65)(H,56,63)(H,57,68)(H,58,66)(H,59,64)(H,60,67)(H,69,70)(H,71,72)(H4,51,52,53)/b19-14+,27-23+/t28-,29-,31+,35-,36-,37+,38-,39+,40-/m0/s1",IHHURHYXJGJEHX-FAJQDCQVSA-N,"8-(3-((diaminomethylene)amino)propyl)-15-(4-hydroxybenzyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802107,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,[Microcystis aeruginosa]CYA548,,"Stereochemistry assumed based on other MC congeners (LC-MS/MS and HRMS analyses unable to confirm this). MC-RY was extensively analysed by 1D and 2D-NMR, hence higher confidence in assigned stereochemistry of this compound. Thiol derivatization of Dha"
CyanoMetDB_1906,"[Asp³,DMAdda5]MC‐RY",,,Microcystin,C50H68N10O13,1017.13,1016.496733,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C50H68N10O13/c1-27(23-28(2)40(62)25-32-11-8-7-9-12-32)14-19-35-29(3)43(65)58-37(48(70)71)20-21-42(64)60(6)31(5)45(67)54-30(4)44(66)57-36(13-10-22-53-50(51)52)46(68)59-39(49(72)73)26-41(63)55-38(47(69)56-35)24-33-15-17-34(61)18-16-33/h7-9,11-12,14-19,23,28-30,35-40,61-62H,5,10,13,20-22,24-26H2,1-4,6H3,(H,54,67)(H,55,63)(H,56,69)(H,57,66)(H,58,65)(H,59,68)(H,70,71)(H,72,73)(H4,51,52,53)/b19-14+,27-23+/t28-,29-,30+,35-,36-,37+,38-,39+,40-/m0/s1",ZNQSNIUNDKWLHS-XEHWMUBVSA-N,"8-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-hydroxybenzyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684751,,10.1021/es305202p,https://pubs.acs.org/doi/10.1021/es305202p,"LC-MS Analysis with Thiol Derivatization to Differentiate [Dhb 7 ]- from [Mdha 7 ]-Microcystins: Analysis of Cyanobacterial Blooms, Planktothrix Cultures and European Crayfish from Lake Steinsfjorden, Norway;Environmental Science & Technology;47;9;;2013;journalArticle;10.1021/es305202p;Miles, Christopher O.; Sandvik, Morten; Haande, Sigrid; Nonga, Hezron; Ballot, Andreas",n.a.,n.a.,n.a.,"field samples, Planktothrix cultures from Lake Steinsfjorden, Norway","Tentative annotation. Stereochemistry assumed based on other microcystin structures. Detected in laboratory culture of Planktothrix agardhii-CYA56/3, -CYA137 and -CYA532. Thiol derivatization"
CyanoMetDB_1907,MC-LL,,,Microcystin,C49H73N7O12,952.14,951.5317211,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H73N7O12/c1-26(2)22-37-46(62)51-35(19-18-28(5)24-29(6)39(68-12)25-34-16-14-13-15-17-34)30(7)42(58)52-36(48(64)65)20-21-40(57)56(11)33(10)45(61)50-32(9)44(60)54-38(23-27(3)4)47(63)55-41(49(66)67)31(8)43(59)53-37/h13-19,24,26-27,29-32,35-39,41H,10,20-23,25H2,1-9,11-12H3,(H,50,61)(H,51,62)(H,52,58)(H,53,59)(H,54,60)(H,55,63)(H,64,65)(H,66,67)/b19-18+,28-24+/t29-,30-,31-,32+,35-,36+,37-,38-,39-,41+/m0/s1",GLDUYXHQWLQPRR-JKUQGWAOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",102580315,,10.1016/0041-0101(93)90338-J,https://linkinghub.elsevier.com/retrieve/pii/004101019390338J,"Identification and characterization of hydrophobic microcystins in Canadian freshwater cyanobacteria;Toxicon;31;12;;1993;journalArticle;10.1016/0041-0101(93)90338-J;Craig, Marcia; McCready, Tara L.; Luu, Hue A.; Smillie, Mark A.; Dubord, Pierre; Holmes, Charles F.B.",n.a.,aeruginosa,[Diehnelt 2006] [Microcystis sp.]CAWBG11,field sample [Craig 1993] containing Microcystis; [Diehnelt 2006]Microcystis,"[Craig et al. 1993] Compound detected in bloom sample (Microcystis aeruginosa). Other cited studies added further certainty to annotation. No stereochemical analyses reported, to date; [Craig 1993] field sample sample - Microcystis; [Diehnelt 2006] [Microcystis sp.]CAWBG11"
CyanoMetDB_1908,MC-LF,,,Microcystin,C52H71N7O12,986.16,985.516071,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H71N7O12/c1-29(2)25-40-50(66)58-44(52(69)70)33(6)46(62)56-41(27-36-17-13-11-14-18-36)49(65)54-38(22-21-30(3)26-31(4)42(71-10)28-37-19-15-12-16-20-37)32(5)45(61)55-39(51(67)68)23-24-43(60)59(9)35(8)48(64)53-34(7)47(63)57-40/h11-22,26,29,31-34,38-42,44H,8,23-25,27-28H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,61)(H,56,62)(H,57,63)(H,58,66)(H,67,68)(H,69,70)/b22-21+,30-26+/t31-,32-,33-,34+,38-,39+,40-,41-,42-,44+/m0/s1",FEVBMCJUKWWWBT-QVWKUIOOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-benzyl-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",16760563,,10.1007/BF02181936,http://link.springer.com/10.1007/BF02181936,"First report of microcystins from a Brazilian isolate of the cyanobacteriumMicrocystis aeruginosa;Journal of Applied Phycology;6;3;;1994;journalArticle;10.1007/BF02181936;Azevedo, Sandra M. F. O.; Evans, William R.; Carmichael, Wayne W.; Namikoshi, Michio",Microcystis,aeruginosa,[Microcystis aeruginosa]NPJB-1,,"Total synthesis achieved, hence high confidence in stereochemical information."
CyanoMetDB_1909,[ADMAdda5]MC‐LR,,Microcystin LF,Microcystin,C50H74N10O13,1023.18,1022.543683,C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC(=O)C)/C,"InChI=1S/C50H74N10O13/c1-26(2)23-38-47(68)59-41(49(71)72)30(6)43(64)56-36(17-14-22-53-50(51)52)46(67)55-35(19-18-27(3)24-28(4)39(73-33(9)61)25-34-15-12-11-13-16-34)29(5)42(63)57-37(48(69)70)20-21-40(62)60(10)32(8)45(66)54-31(7)44(65)58-38/h11-13,15-16,18-19,24,26,28-31,35-39,41H,8,14,17,20-23,25H2,1-7,9-10H3,(H,54,66)(H,55,67)(H,56,64)(H,57,63)(H,58,65)(H,59,68)(H,69,70)(H,71,72)(H4,51,52,53)/b19-18+,27-24+/t28-,29-,30-,31+,35-,36-,37+,38-,39-,41+/m0/s1",DDMJZWZMKZNCTP-RASTYGMGSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-((diaminomethylene)amino)propyl)-8-isobutyl-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",14752800,DTXSID00891475,10.1021/jo00312a019,https://pubs.acs.org/doi/abs/10.1021/jo00312a019,"Structures of three new cyclic heptapeptide hepatotoxins produced by the cyanobacterium (blue-green alga) Nostoc sp. strain 152;The Journal of Organic Chemistry;55;25;;1990;journalArticle;10.1021/jo00312a019;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Sivonen, Kaarina; Carmichael, Wayne W.",Nostoc,n.a.,152; IO-102-I,,
CyanoMetDB_1910,MC-YA,,,Microcystin,C49H65N7O13,960.08,959.4640355,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H65N7O13/c1-26(23-27(2)39(69-9)25-33-13-11-10-12-14-33)15-20-36-28(3)42(59)53-37(48(65)66)21-22-40(58)56(8)32(7)46(63)51-31(6)45(62)54-38(24-34-16-18-35(57)19-17-34)47(64)55-41(49(67)68)29(4)43(60)50-30(5)44(61)52-36/h10-20,23,27-31,36-39,41,57H,7,21-22,24-25H2,1-6,8-9H3,(H,50,60)(H,51,63)(H,52,61)(H,53,59)(H,54,62)(H,55,64)(H,65,66)(H,67,68)/b20-15+,26-23+/t27-,28-,29-,30-,31+,36-,37+,38-,39-,41+/m0/s1",JODAXCVFVMHOSN-LZUXOUIYSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101619977,,10.1039/p19850002747,http://xlink.rsc.org/?DOI=p19850002747,"Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa;Journal of the Chemical Society, Perkin Transactions 1;;;;1985;journalArticle;10.1039/p19850002747;Botes, Dawie P.; Wessels, Philippus L.; Kruger, Hel�ne; Runnegar, Maria T. C.; Santikarn, Sitthivet; Smith, Richard J.; Barna, Jennifer C. J.; Williams, Dudley H.",Microcystis,aeruginosa,[Microcystis aeruginosa]UTEX 2670,,"Botes et al. originally reported the possible occurrence of MC-YA, but detection was based only on 1H NMR (insufficient quantities for FAB-MS). No molecular formula proposed.
Paper by Miles used a combination of product and precursor ion scans (the latter focussing on 135 m/z Adda fragment) of both the underivatised and the thiol-derivatised MCs, in combination with HRMS and characterisation of a related MC, to provide the putative annotation of MC-YA.
There is no definite 1D and 2D-NMR analysis of MC-YA reported in the literature so far. "
CyanoMetDB_1911,"[D-Leu1,Dha7]MC-LR",,,Microcystin,C51H78N10O12,1023.22,1022.580068,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H78N10O12/c1-27(2)23-38-47(67)60-39(24-28(3)4)48(68)61-42(50(71)72)32(8)44(64)57-36(17-14-22-54-51(52)53)46(66)56-35(19-18-29(5)25-30(6)40(73-10)26-34-15-12-11-13-16-34)31(7)43(63)58-37(49(69)70)20-21-41(62)55-33(9)45(65)59-38/h11-13,15-16,18-19,25,27-28,30-32,35-40,42H,9,14,17,20-24,26H2,1-8,10H3,(H,55,62)(H,56,66)(H,57,64)(H,58,63)(H,59,65)(H,60,67)(H,61,68)(H,69,70)(H,71,72)(H4,52,53,54)/b19-18+,29-25+/t30-,31-,32-,35-,36-,37+,38+,39-,40-,42+/m0/s1",KOIJCFISWXUGAO-NEFNCPLOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-12,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684763,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Nostoc; Microcystis,[Nostoc]sp.; [Microcystis]aeruginosa,[Nostoc sp.]UK8911A;[Microcystis aeruginosa]NPLJ-4,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1912,[D-Val1]MC‐LR,,,Microcystin,C51H78N10O12,1023.22,1022.580068,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(C)C)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H78N10O12/c1-27(2)24-38-47(67)60-42(50(71)72)32(8)44(64)56-36(18-15-23-54-51(52)53)46(66)55-35(20-19-29(5)25-30(6)39(73-11)26-34-16-13-12-14-17-34)31(7)43(63)57-37(49(69)70)21-22-40(62)61(10)33(9)45(65)59-41(28(3)4)48(68)58-38/h12-14,16-17,19-20,25,27-28,30-32,35-39,41-42H,9,15,18,21-24,26H2,1-8,10-11H3,(H,55,66)(H,56,64)(H,57,63)(H,58,68)(H,59,65)(H,60,67)(H,69,70)(H,71,72)(H4,52,53,54)/b20-19+,29-25+/t30-,31-,32-,35-,36-,37+,38-,39-,41+,42+/m0/s1",QEBMEJHOLOTQNA-ZTAMYMMKSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-5-isopropyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684764,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Microcystis,aeruginosa,[Microcystis aeruginosa]NPLJ-4,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1913,"[D-Leu1,DMAdda5]MC-LR",,,Microcystin,C51H78N10O12,1023.22,1022.5801,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C51H78N10O12/c1-27(2)23-38-47(68)59-39(24-28(3)4)48(69)60-42(50(72)73)32(8)44(65)56-36(17-14-22-54-51(52)53)46(67)55-35(19-18-29(5)25-30(6)40(62)26-34-15-12-11-13-16-34)31(7)43(64)57-37(49(70)71)20-21-41(63)61(10)33(9)45(66)58-38/h11-13,15-16,18-19,25,27-28,30-32,35-40,42,62H,9,14,17,20-24,26H2,1-8,10H3,(H,55,67)(H,56,65)(H,57,64)(H,58,66)(H,59,68)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b19-18+,29-25+/t30-,31-,32-,35-,36-,37+,38+,39-,40-,42+/m0/s1",ZHYBUNDBGXRGAL-NEFNCPLOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,8-diisobutyl-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802449,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Identified by LC-MS/MS but closely related [D-Leu1]MC-LR analysed, in depth, by 1D and 2D-NMR spectroscopy. Thiol derivatization H2O2 oxidation also used."
CyanoMetDB_1914,"[D-Leu1,dmAdda5]MC-LR (isomer 1)","[D-Leu1,(8-desmethyl)Adda5]MC-LR is depicted",,Microcystin,C51H78N10O12,1023.22,1022.5801,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/C[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C51H78N10O12/c1-28(2)25-39-47(67)59-40(26-29(3)4)48(68)60-42(50(71)72)32(7)44(64)56-37(17-14-24-54-51(52)53)46(66)55-36(21-19-30(5)18-20-35(73-10)27-34-15-12-11-13-16-34)31(6)43(63)57-38(49(69)70)22-23-41(62)61(9)33(8)45(65)58-39/h11-13,15-16,18-19,21,28-29,31-32,35-40,42H,8,14,17,20,22-27H2,1-7,9-10H3,(H,55,66)(H,56,64)(H,57,63)(H,58,65)(H,59,67)(H,60,68)(H,69,70)(H,71,72)(H4,52,53,54)/b21-19+,30-18+/t31-,32-,35+,36-,37-,38+,39+,40-,42+/m0/s1",SCAWNGGFANAHEA-YFVOVKPZSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((R,1E,3E)-6-methoxy-3-methyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802322,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ",Desmethylation site on ADDA not fully elucidated but distinct from O-demethylation and isomer 2 - assigned as (8-desmethyl)Adda. Desmethyl somewhere between C-2 and C-8 based on MS/MS. Thiol derivatization and H2O2 used.
CyanoMetDB_1915,"[D-Leu1,dmAdda5]MC-LR (isomer 2)","[D-Leu1,(6-desmethyl)Adda5]MC-LR is depicted",,Microcystin,C51H78N10O12,1023.22,1022.5801,CC(C)C[C@H]1NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@H](\C=C\C=C\[C@H](C)[C@H](Cc2ccccc2)OC)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC1=O)C(=O)O)C(=O)O,"InChI=1S/C51H78N10O12/c1-28(2)25-38-47(67)59-39(26-29(3)4)48(68)60-42(50(71)72)32(7)44(64)56-36(21-16-24-54-51(52)53)46(66)55-35(20-15-14-17-30(5)40(73-10)27-34-18-12-11-13-19-34)31(6)43(63)57-37(49(69)70)22-23-41(62)61(9)33(8)45(65)58-38/h11-15,17-20,28-32,35-40,42H,8,16,21-27H2,1-7,9-10H3,(H,55,66)(H,56,64)(H,57,63)(H,58,65)(H,59,67)(H,60,68)(H,69,70)(H,71,72)(H4,52,53,54)/b17-14+,20-15+/t30-,31-,32-,35-,36-,37+,38+,39-,40-,42+/m0/s1",ZUIGOPVLTVMXIU-UIZUBYECSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-5-methyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802460,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ",Desmethylation site on ADDA not fully elucidated but distinct from O-demethylation and isomer 1 - assigned as (6-desmethyl)Adda. Desmethyl somewhere between C-2 and C-8 based on MS/MS
CyanoMetDB_1916,MC-LY,,,Microcystin,C52H71N7O13,1002.16,1001.510986,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H71N7O13/c1-28(2)24-40-50(67)58-44(52(70)71)32(6)46(63)56-41(26-36-17-19-37(60)20-18-36)49(66)54-38(21-16-29(3)25-30(4)42(72-10)27-35-14-12-11-13-15-35)31(5)45(62)55-39(51(68)69)22-23-43(61)59(9)34(8)48(65)53-33(7)47(64)57-40/h11-21,25,28,30-33,38-42,44,60H,8,22-24,26-27H2,1-7,9-10H3,(H,53,65)(H,54,66)(H,55,62)(H,56,63)(H,57,64)(H,58,67)(H,68,69)(H,70,71)/b21-16+,29-25+/t30-,31-,32-,33+,38-,39+,40-,41-,42-,44+/m0/s1",SIGQAYSWORHPPH-WSTSHCHISA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(4-hydroxybenzyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",71312414,,10.1016/0041-0101(89)90051-2,https://linkinghub.elsevier.com/retrieve/pii/0041010189900512,,Microcystis,aeruginosa,[Microcystis aeruginosa]UAM-1303,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1917,MC-YM,,Microcystin LY,Microcystin,C51H69N7O13S,1020.2,1019.467406,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCSC)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H69N7O13S/c1-28(25-29(2)41(71-8)27-34-13-11-10-12-14-34)15-20-37-30(3)44(61)55-39(50(67)68)21-22-42(60)58(7)33(6)47(64)52-32(5)46(63)56-40(26-35-16-18-36(59)19-17-35)49(66)57-43(51(69)70)31(4)45(62)54-38(23-24-72-9)48(65)53-37/h10-20,25,29-32,37-41,43,59H,6,21-24,26-27H2,1-5,7-9H3,(H,52,64)(H,53,65)(H,54,62)(H,55,61)(H,56,63)(H,57,66)(H,67,68)(H,69,70)/b20-15+,28-25+/t29-,30-,31-,32+,37-,38-,39+,40-,41-,43+/m0/s1",CZNWJIGJNMVYOS-PQCSFXGESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-15-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683864,DTXSID60891476,10.1039/p19850002747,http://xlink.rsc.org/?DOI=p19850002747,"Structural studies on cyanoginosins-LR, -YR, -YA, and -YM, peptide toxins from Microcystis aeruginosa;Journal of the Chemical Society, Perkin Transactions 1;;;;1985;journalArticle;10.1039/p19850002747;Botes, Dawie P.; Wessels, Philippus L.; Kruger, Hel�ne; Runnegar, Maria T. C.; Santikarn, Sitthivet; Smith, Richard J.; Barna, Jennifer C. J.; Williams, Dudley H.",Microcystis,aeruginosa,[Microcystis aeruginosa]UTEX 2670,,Sterochemistry defined by Botes et al. 1985.
CyanoMetDB_1918,[Dha7]MC-RR,,,Microcystin,C48H73N13O12,1024.17,1023.550165,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H73N13O12/c1-25(23-26(2)36(73-7)24-31-13-9-8-10-14-31)17-18-32-27(3)39(63)60-35(45(69)70)19-20-37(62)55-29(5)41(65)56-30(6)42(66)59-34(16-12-22-54-48(51)52)44(68)61-38(46(71)72)28(4)40(64)58-33(43(67)57-32)15-11-21-53-47(49)50/h8-10,13-14,17-18,23,26-28,30,32-36,38H,5,11-12,15-16,19-22,24H2,1-4,6-7H3,(H,55,62)(H,56,65)(H,57,67)(H,58,64)(H,59,66)(H,60,63)(H,61,68)(H,69,70)(H,71,72)(H4,49,50,53)(H4,51,52,54)/b18-17+,25-23+/t26-,27-,28-,30+,32-,33-,34-,35+,36-,38+/m0/s1",ANEDRERLGQEWQI-UAWDZTONSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6441234,,10.1016/0041-0101(92)90054-9,https://linkinghub.elsevier.com/retrieve/pii/0041010192900549,"Structure determination and toxicity of a new microcystin from Microcystis aeruginosa strain 205;Toxicon;30;9;;1992;journalArticle;10.1016/0041-0101(92)90054-9;Kiviranta, Jari; Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Carmichael, Wayne W.; Rinehart, Kenneth L.",Microcystis,aeruginosa,[Microcystis aeruginosa]205,,Stereochemistry defined through chiral amino acid analysis.
CyanoMetDB_1919,"[Gly1,D-Asp³,Dhb7]MC‐Rhar",,,Microcystin,C48H73N13O12,1024.17,1023.550165,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)C(=CC)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)CCCCNC(=N)N)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H73N13O12/c1-6-31-42(66)55-26-40(64)58-34(16-12-22-54-48(51)52)44(68)61-36(46(71)72)25-39(63)57-33(15-10-11-21-53-47(49)50)43(67)59-32(29(4)41(65)60-35(45(69)70)19-20-38(62)56-31)18-17-27(2)23-28(3)37(73-5)24-30-13-8-7-9-14-30/h6-9,13-14,17-18,23,28-29,32-37H,10-12,15-16,19-22,24-26H2,1-5H3,(H,55,66)(H,56,62)(H,57,63)(H,58,64)(H,59,67)(H,60,65)(H,61,68)(H,69,70)(H,71,72)(H4,49,50,53)(H4,51,52,54)/b18-17+,27-23+,31-6?/t28-,29-,32-,33-,34-,35+,36+,37-/m0/s1",XXDSTGLUHVLWDL-QXXCSYONSA-N,"(8S,11R,15S,18S,19S,22R)-2-ethylidene-15-(4-guanidinobutyl)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-19-methyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683804,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)",Stereochemistry partially defined by advanced Marfey amino acid analysis. Undefined E/Z isomerism at Dhb.
CyanoMetDB_1920,"[Gly1,D-Asp3]MC-RHar",,,Microcystin,C48H73N13O12,1024.17,1023.5502,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H73N13O12/c1-27(23-28(2)37(73-6)24-31-13-8-7-9-14-31)17-18-32-29(3)41(65)59-35(45(69)70)19-20-40(64)61(5)30(4)42(66)55-26-39(63)57-34(16-12-22-54-48(51)52)44(68)60-36(46(71)72)25-38(62)56-33(43(67)58-32)15-10-11-21-53-47(49)50/h7-9,13-14,17-18,23,28-29,32-37H,4,10-12,15-16,19-22,24-26H2,1-3,5-6H3,(H,55,66)(H,56,62)(H,57,63)(H,58,67)(H,59,65)(H,60,68)(H,69,70)(H,71,72)(H4,49,50,53)(H4,51,52,54)/b18-17+,27-23+/t28-,29-,32-,33-,34-,35+,36+,37-/m0/s1",OFONZIYCWCBBSK-QTEMMPDJSA-N,"(8S,11R,15S,18S,19S,22R)-15-(4-guanidinobutyl)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683837,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",n.a.,n.a.,n.a.,"field samples, from various benthic mats",From Antarctica. Compound MC-4 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1921,[DMAdda5]MC-RR,,,Microcystin,C48H73N13O12,1024.17,1023.5502,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@@H](O)Cc1ccccc1,"InChI=1S/C48H73N13O12/c1-25(23-26(2)36(62)24-31-13-9-8-10-14-31)17-18-32-27(3)39(64)59-35(45(70)71)19-20-37(63)61(7)30(6)42(67)55-29(5)41(66)58-34(16-12-22-54-48(51)52)44(69)60-38(46(72)73)28(4)40(65)57-33(43(68)56-32)15-11-21-53-47(49)50/h8-10,13-14,17-18,23,26-29,32-36,38,62H,6,11-12,15-16,19-22,24H2,1-5,7H3,(H,55,67)(H,56,68)(H,57,65)(H,58,66)(H,59,64)(H,60,69)(H,70,71)(H,72,73)(H4,49,50,53)(H4,51,52,54)/b18-17+,25-23+/t26-,27-,28-,29+,32-,33-,34-,35+,36-,38+/m0/s1",QNXSMJGNFUUQFQ-BLNINCLDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683857,,10.1016/j.toxicon.2019.06.006,https://linkinghub.elsevier.com/retrieve/pii/S0041010119301795,"Comprehensive multi-technique approach reveals the high diversity of microcystins in field collections and an associated isolate of Microcystis aeruginosa from a Turkish lake;Toxicon;167;;;2019;journalArticle;10.1016/j.toxicon.2019.06.006;Yilmaz, Mete; Foss, Amanda J.; Miles, Christopher O.; Özen, Mihriban; Demir, Nilsun; Balcı, Muharrem; Beach, Daniel G.",n.a.,n.a.,n.a.,"field sample, field collections and an associated isolate of Microcystis aeruginosa from Lake Uluabat, Turkey",Thiol derivatization and S-oxidation
CyanoMetDB_1922,MC-LW,,,Microcystin,C54H72N8O12,1025.2,1024.52697,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C54H72N8O12/c1-29(2)24-42-52(69)61-46(54(72)73)33(6)48(65)59-43(27-37-28-55-40-19-15-14-18-38(37)40)51(68)57-39(21-20-30(3)25-31(4)44(74-10)26-36-16-12-11-13-17-36)32(5)47(64)58-41(53(70)71)22-23-45(63)62(9)35(8)50(67)56-34(7)49(66)60-42/h11-21,25,28-29,31-34,39,41-44,46,55H,8,22-24,26-27H2,1-7,9-10H3,(H,56,67)(H,57,68)(H,58,64)(H,59,65)(H,60,66)(H,61,69)(H,70,71)(H,72,73)/b21-20+,30-25+/t31-,32-,33-,34+,39-,41+,42-,43-,44-,46+/m0/s1",CJIASZBWXIFQMU-LNXRSHCCSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(indolin-3-ylmethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",16760564,,10.1016/0021-9673(95)00438-S,https://linkinghub.elsevier.com/retrieve/pii/002196739500438S,"Mass spectral analyses of microcystins from toxic cyanobacteria using on-line chromatographic and electrophoretic separations;Journal of Chromatography A;712;1;;1995;journalArticle;10.1016/0021-9673(95)00438-S;Bateman, K.P; Thibault, P; Douglas, D.J; White, R.L",Microcystis,aeruginosa,[Microcystis aeruginosa]PCC7820,,Characterisation is based on MS/MS and therefore stereochemistries are assumed. 15N labeling used to support annotation of fragment ions.
CyanoMetDB_1923,MC-WL,,Microcystin LW,Microcystin,C54H72N8O12,1025.2,1024.52697,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2c[NH]c3ccccc32)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C54H72N8O12/c1-29(2)24-42-51(68)57-39(21-20-30(3)25-31(4)44(74-10)26-36-16-12-11-13-17-36)32(5)47(64)58-41(53(70)71)22-23-45(63)62(9)35(8)50(67)56-34(7)49(66)60-43(27-37-28-55-40-19-15-14-18-38(37)40)52(69)61-46(54(72)73)33(6)48(65)59-42/h11-21,25,28-29,31-34,39,41-44,46,55H,8,22-24,26-27H2,1-7,9-10H3,(H,56,67)(H,57,68)(H,58,64)(H,59,65)(H,60,66)(H,61,69)(H,70,71)(H,72,73)/b21-20+,30-25+/t31-,32-,33-,34+,39-,41+,42-,43-,44-,46+/m0/s1",STMJLSNDMMJCDL-LNXRSHCCSA-N,"8-((1H-indol-3-yl)methyl)-15-isobutyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802332,DTXSID70891285,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,,Structure defined using LC-MS/MS (unit res.) and HR-ESI-MS analysis. Stereochemistry assumed based on other MC congeners. Thiol derivatization used.
CyanoMetDB_1924,[D-Asp3]MC-RCit,,,Microcystin,C48H72N12O13,1025.16,1024.5342,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(N)=O)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N12O13/c1-26(23-27(2)37(73-7)24-31-13-9-8-10-14-31)17-18-32-28(3)40(63)58-35(45(68)69)19-20-39(62)60(6)30(5)42(65)54-29(4)41(64)57-34(16-11-21-52-47(49)50)44(67)59-36(46(70)71)25-38(61)55-33(43(66)56-32)15-12-22-53-48(51)72/h8-10,13-14,17-18,23,27-29,32-37H,5,11-12,15-16,19-22,24-25H2,1-4,6-7H3,(H,54,65)(H,55,61)(H,56,66)(H,57,64)(H,58,63)(H,59,67)(H,68,69)(H,70,71)(H4,49,50,52)(H3,51,53,72)/b18-17+,26-23+/t27-,28-,29+,32-,33-,34-,35+,36+,37-/m0/s1",MWOUSUQNUHRYLP-LTPNNWFFSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-15-(3-ureidopropyl)-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683813,,10.3390/md17110643,https://www.mdpi.com/1660-3397/17/11/643,"Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling;Marine Drugs;17;11;;2019;journalArticle;10.3390/md17110643;Mallia, Vittoria; Uhlig, Silvio; Rafuse, Cheryl; Meija, Juris; Miles, Christopher O.",Planktothrix ,prolifica ,NIVA-CYA 544,,"Thiol derivatization, 15N-labelling, S-oxidation, LC-HRMS/MS"
CyanoMetDB_1925,"[D-Asp3,ADMAdda5,Thr7]MC-LR",,,Microcystin,C49H74N10O14,1027.17,1026.538597,O=C(CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC1=CC=CC=C1)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N2)CC(C)C)=O)=O)=O)=O)N[C@@H](C(O)C)C(N[C@@H](C2=O)C)=O,"InChI=1S/C49H74N10O14/c1-25(2)21-36-45(67)58-37(48(71)72)24-40(63)54-34(15-12-20-52-49(50)51)44(66)55-33(17-16-26(3)22-27(4)38(73-31(8)61)23-32-13-10-9-11-14-32)28(5)42(64)56-35(47(69)70)18-19-39(62)59-41(30(7)60)46(68)53-29(6)43(65)57-36/h9-11,13-14,16-17,22,25,27-30,33-38,41,60H,12,15,18-21,23-24H2,1-8H3,(H,53,68)(H,54,63)(H,55,66)(H,56,64)(H,57,65)(H,58,67)(H,59,62)(H,69,70)(H,71,72)(H4,50,51,52)/b17-16+,26-22+/t27-,28-,29+,30?,33-,34-,35+,36-,37+,38-,41-/m0/s1",QJNPZTRQEFLDPL-KDMVTSMASA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-2-(1-hydroxyethyl)-8-isobutyl-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802284,,10.3390/toxins10040147,http://www.mdpi.com/2072-6651/10/4/147,"Toxic Cyanobacteria in Svalbard: Chemical Diversity of Microcystins Detected Using a Liquid Chromatography Mass Spectrometry Precursor Ion Screening Method;Toxins;10;4;;2018;journalArticle;10.3390/toxins10040147;Kleinteich, Julia; Puddick, Jonathan; Wood, Susanna; Hildebrand, Falk; Laughinghouse IV, H.; Pearce, David; Dietrich, Daniel; Wilmotte, Annick",n.a.,n.a.,n.a.,"field sample, archipelago in the North Atlantic Ocean at 77°50′ N and 19°50′ Ein the vicinity of Longyearbyen, Björndalen and Colesbukta",Thiol derivatisation used to support identification. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1926,[seco-1/2]MC-HilR,H‐(L‐Hil)‐(MeAsp)‐(L‐Arg)‐(Adda)‐(D‐Glu)‐(Mdha)‐(D‐Ala)‐OH,,Microcystin,C50H78N10O13,1027.21,1026.574983,O=C(O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](N)C[C@@H](C)CC)C(=O)O)/C=C/C(/C)=C/[C@H](C)[C@@H](OC)Cc1ccccc1)C(=O)O,"InChI=1S/C50H78N10O13/c1-11-27(2)25-35(51)45(65)59-41(49(71)72)31(6)43(63)57-37(18-15-23-54-50(52)53)46(66)56-36(20-19-28(3)24-29(4)39(73-10)26-34-16-13-12-14-17-34)30(5)42(62)58-38(48(69)70)21-22-40(61)60(9)33(8)44(64)55-32(7)47(67)68/h12-14,16-17,19-20,24,27,29-32,35-39,41H,8,11,15,18,21-23,25-26,51H2,1-7,9-10H3,(H,55,64)(H,56,66)(H,57,63)(H,58,62)(H,59,65)(H,67,68)(H,69,70)(H,71,72)(H4,52,53,54)/b20-19+,28-24+/t27-,29-,30-,31-,32+,35-,36-,37-,38+,39-,41+/m0/s1",TWKTYHOANJLEMM-RZMACXILSA-N,"N2-((2S,3S,4E,6E,8S,9S)-3-((S)-2-((2S,3R)-3-((2S,4S)-2-amino-4-methylhexanamido)-3-carboxy-2-methylpropanamido)-5-guanidinopentanamido)-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)-N5-(3-(((R)-1-carboxyethyl)amino)-3-oxoprop-1-en-2-yl)-N5-methyl-D-glutamine",155802340,,10.1021/jo00117a017,https://pubs.acs.org/doi/abs/10.1021/jo00117a017,"Seven More Microcystins from Homer Lake Cells: Application of the General Method for Structure Assignment of Peptides Containing .alpha.,.beta.-Dehydroamino Acid Unit(s);The Journal of Organic Chemistry;60;12;;1995;journalArticle;10.1021/jo00117a017;Namikoshi, Michio; Sun, Furong; Choi, Byoung Wook; Rinehart, Kenneth L.; Carmichael, Wayne W.; Evans, William R.; Beasley, Val R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria M. aeruginosa dominant plus smaller quantities of M. viridis and M. wesenbergii,Chemical degradation product of MC-HilR.
CyanoMetDB_1927,"[D-Asp3,Ser7]MC-RR",,,Microcystin,C47H73N13O13,1028.16,1027.5451,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)[C@H](CO)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H73N13O13/c1-25(21-26(2)36(73-5)22-29-11-7-6-8-12-29)15-16-30-27(3)39(64)59-33(44(69)70)17-18-37(62)56-35(24-61)43(68)54-28(4)40(65)58-32(14-10-20-53-47(50)51)42(67)60-34(45(71)72)23-38(63)55-31(41(66)57-30)13-9-19-52-46(48)49/h6-8,11-12,15-16,21,26-28,30-36,61H,9-10,13-14,17-20,22-24H2,1-5H3,(H,54,68)(H,55,63)(H,56,62)(H,57,66)(H,58,65)(H,59,64)(H,60,67)(H,69,70)(H,71,72)(H4,48,49,52)(H4,50,51,53)/b16-15+,25-21+/t26-,27-,28+,30-,31-,32-,33+,34+,35-,36-/m0/s1",WSHYAOXMZXNUAQ-MPCPOGOHSA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802402,,10.3390/toxins10040147,http://www.mdpi.com/2072-6651/10/4/147,"Toxic Cyanobacteria in Svalbard: Chemical Diversity of Microcystins Detected Using a Liquid Chromatography Mass Spectrometry Precursor Ion Screening Method;Toxins;10;4;;2018;journalArticle;10.3390/toxins10040147;Kleinteich, Julia; Puddick, Jonathan; Wood, Susanna; Hildebrand, Falk; Laughinghouse IV, H.; Pearce, David; Dietrich, Daniel; Wilmotte, Annick",n.a.,n.a.,n.a.,"field sample, archipelago in the North Atlantic Ocean at 77°50′ N and 19°50′ Ein the vicinity of Longyearbyen, Björndalen and Colesbukta",InChI and SMILES codes assume L-serine in position 7 of structure. Thiol derivatization used.
CyanoMetDB_1928,MC-NfkAba,MC‐NfkAbu (oxidised W),,Microcystin,C52H68N8O14,1029.14,1028.485499,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C(C=CC=C3)=C3NC=O)=O)=O)=O)=O)=O,"InChI=1S/C52H68N8O14/c1-10-36-49(68)56-37(21-20-28(2)24-29(3)42(74-9)25-34-16-12-11-13-17-34)30(4)45(64)57-39(51(70)71)22-23-43(63)60(8)33(7)48(67)54-32(6)47(66)58-40(26-41(62)35-18-14-15-19-38(35)53-27-61)50(69)59-44(52(72)73)31(5)46(65)55-36/h11-21,24,27,29-32,36-37,39-40,42,44H,7,10,22-23,25-26H2,1-6,8-9H3,(H,53,61)(H,54,67)(H,55,65)(H,56,68)(H,57,64)(H,58,66)(H,59,69)(H,70,71)(H,72,73)/b21-20+,28-24+/t29-,30-,31-,32+,36-,37-,39+,40-,42-,44+/m0/s1",USXZNWBTSVNVRL-NHEVINJRSA-N,"15-ethyl-8-(2-(2-formamidophenyl)-2-oxoethyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683826,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,n.a.,CAWBG11,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1929,MC-M(O)R,MC‐M(O)R,,Microcystin,C48H72N10O13S,1029.21,1028.500103,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCS(C)=O)=O)=O)=O)=O,"InChI=1S/C48H72N10O13S/c1-26(24-27(2)37(71-8)25-32-14-11-10-12-15-32)17-18-33-28(3)40(60)56-36(46(66)67)19-20-38(59)58(7)31(6)43(63)52-30(5)42(62)55-35(21-23-72(9)70)45(65)57-39(47(68)69)29(4)41(61)54-34(44(64)53-33)16-13-22-51-48(49)50/h10-12,14-15,17-18,24,27-30,33-37,39H,6,13,16,19-23,25H2,1-5,7-9H3,(H,52,63)(H,53,64)(H,54,61)(H,55,62)(H,56,60)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,26-24+/t27-,28-,29-,30+,33-,34-,35-,36+,37-,39+,72?/m0/s1",RUYWGLHBHWTKHT-SSYCBDRMSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-8-(2-(methylsulfinyl)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101619978,,10.1021/jo00029a016,https://pubs.acs.org/doi/abs/10.1021/jo00029a016,"Identification of 12 hepatotoxins from a Homer Lake bloom of the cyanobacteria Microcystis aeruginosa, Microcystis viridis, and Microcystis wesenbergii: nine new microcystins;The Journal of Organic Chemistry;57;3;;1992;journalArticle;10.1021/jo00029a016;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Stotts, Richard R.; Dahlem, Andrew M.; Beasley, Val R.; Carmichael, Wayne W.; Evans, William R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria Microcystis aeruginosa (also contained Microcystis viridis and Microcystis wesenbergii),likely oxidation artifact (Methionine oxidation)
CyanoMetDB_1930,"[D-Asp3,(E)-Dhb7]MC-HphR",Cyanoviridin-RR,,Microcystin,C52H72N10O12,1029.19,1028.533118,O=C(N/C(C(N[C@@H](C1=O)C)=O)=C/C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O12/c1-7-36-47(67)56-33(5)46(66)60-39(23-21-34-15-10-8-11-16-34)49(69)62-41(51(72)73)29-44(64)58-38(19-14-26-55-52(53)54)48(68)59-37(32(4)45(65)61-40(50(70)71)24-25-43(63)57-36)22-20-30(2)27-31(3)42(74-6)28-35-17-12-9-13-18-35/h7-13,15-18,20,22,27,31-33,37-42H,14,19,21,23-26,28-29H2,1-6H3,(H,56,67)(H,57,63)(H,58,64)(H,59,68)(H,60,66)(H,61,65)(H,62,69)(H,70,71)(H,72,73)(H4,53,54,55)/b22-20+,30-27+,36-7+/t31-,32-,33+,37-,38-,39-,40+,41+,42-/m0/s1",BQQVLFQTGZVVKM-ANYUHGQASA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801662,,N/A,http://dl.uncw.edu/Etd/2011-2/r1/isaacsj/justinisaacs.pdf,,Oscillatoria/Planktothrix,rubescens,UTCC507,,
CyanoMetDB_1931,[D-Asp3]MC‐HphR,,,Microcystin,C52H72N10O12,1029.19,1028.533118,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H72N10O12/c1-30(27-31(2)42(74-7)28-36-17-12-9-13-18-36)20-22-37-32(3)45(65)60-40(50(70)71)24-25-44(64)62(6)34(5)47(67)56-33(4)46(66)59-39(23-21-35-15-10-8-11-16-35)49(69)61-41(51(72)73)29-43(63)57-38(48(68)58-37)19-14-26-55-52(53)54/h8-13,15-18,20,22,27,31-33,37-42H,5,14,19,21,23-26,28-29H2,1-4,6-7H3,(H,56,67)(H,57,63)(H,58,68)(H,59,66)(H,60,65)(H,61,69)(H,70,71)(H,72,73)(H4,53,54,55)/b22-20+,30-27+/t31-,32-,33+,37-,38-,39-,40+,41+,42-/m0/s1",SNSOAISNMANBOH-PAAISOOGSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684705,,10.1007/s00203-004-0711-3,http://link.springer.com/10.1007/s00203-004-0711-3,"Diversity of coexisting Planktothrix (Cyanobacteria) chemotypes deduced by mass spectral analysis of microystins and other oligopeptides;Archives of Microbiology;182;4;;2004;journalArticle;10.1007/s00203-004-0711-3;Welker, Martin; Christiansen, Guntram; von Döhren, Hans",Planktothrix,sp.,[Planktothrix sp.]Max06,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1932,[Dha7]MC-HphR,,,Microcystin,C52H72N10O12,1029.19,1028.533118,O=C(NC(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O12/c1-29(27-30(2)41(74-7)28-36-17-12-9-13-18-36)20-22-37-31(3)44(64)61-40(50(70)71)24-25-42(63)56-33(5)46(66)57-34(6)47(67)60-39(23-21-35-15-10-8-11-16-35)49(69)62-43(51(72)73)32(4)45(65)59-38(48(68)58-37)19-14-26-55-52(53)54/h8-13,15-18,20,22,27,30-32,34,37-41,43H,5,14,19,21,23-26,28H2,1-4,6-7H3,(H,56,63)(H,57,66)(H,58,68)(H,59,65)(H,60,67)(H,61,64)(H,62,69)(H,70,71)(H,72,73)(H4,53,54,55)/b22-20+,29-27+/t30-,31-,32-,34+,37-,38-,39-,40+,41-,43+/m0/s1",DCAGLOYSRZSAJK-ZIHFDJJESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683849,,10.1021/tx00029a011,https://pubs.acs.org/doi/abs/10.1021/tx00029a011,"Structures of three new homotyrosine-containing microcystins and a new homophenylalanine variant from Anabaena sp. strain 66;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a011;Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Carmichael, Wayne W.; Rouhiainen, Leo; Luukkainen, Raija; Rinehart, Kenneth L.",Anabaena,n.a.,[Anabaena sp.]66,,"Stereochemistry largely defined by chiral GC-MS analysis, though due to insufficient amounts the cited reference assumed L-Arg in position 4. Cited reference highlights need for further characterisation to be performed of this compound."
CyanoMetDB_1933,MC‐LV,,,Microcystin,C48H71N7O12,938.12,937.516071,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)C(C)C)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H71N7O12/c1-25(2)22-36-45(61)54-40(48(65)66)30(8)42(58)53-39(26(3)4)46(62)50-34(19-18-27(5)23-28(6)37(67-12)24-33-16-14-13-15-17-33)29(7)41(57)51-35(47(63)64)20-21-38(56)55(11)32(10)44(60)49-31(9)43(59)52-36/h13-19,23,25-26,28-31,34-37,39-40H,10,20-22,24H2,1-9,11-12H3,(H,49,60)(H,50,62)(H,51,57)(H,52,59)(H,53,58)(H,54,61)(H,63,64)(H,65,66)/b19-18+,27-23+/t28-,29-,30-,31+,34-,35+,36-,37-,39-,40+/m0/s1",AJUZGGJRRWZCKO-LGJGRGOKSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-8-isobutyl-15-isopropyl-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684729,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Hapalosiphon,hibernicus,[Hapalosiphon hibernicus]BZ-3-1,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1934,MC‐RF,,,Microcystin,C52H72N10O12,1029.19,1028.533118,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=CC=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C52H72N10O12/c1-29(26-30(2)41(74-8)28-36-18-13-10-14-19-36)21-22-37-31(3)44(64)59-39(50(70)71)23-24-42(63)62(7)34(6)47(67)56-33(5)46(66)58-38(20-15-25-55-52(53)54)48(68)61-43(51(72)73)32(4)45(65)60-40(49(69)57-37)27-35-16-11-9-12-17-35/h9-14,16-19,21-22,26,30-33,37-41,43H,6,15,20,23-25,27-28H2,1-5,7-8H3,(H,56,67)(H,57,69)(H,58,66)(H,59,64)(H,60,65)(H,61,68)(H,70,71)(H,72,73)(H4,53,54,55)/b22-21+,29-26+/t30-,31-,32-,33+,37-,38-,39+,40-,41-,43+/m0/s1",IDRFLSYJDPQZQQ-POWPIGGBSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-benzyl-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684757,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry assumed based on other MC congeners. Microcystin-containing cyanobacterial bloom samples (20 L) from Mwanza Gulf in Lake Victoria, Tanzania, in 2010"
CyanoMetDB_1935,[D-Asp³]MC‐M(O2)R,[Asp3]MC‐M(O2)R (oxidation artefact),,Microcystin,C47H70N10O14S,1031.18,1030.479368,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCS(C)(=O)=O)=O)=O)=O)=O,"InChI=1S/C47H70N10O14S/c1-26(23-27(2)37(71-7)24-31-13-10-9-11-14-31)16-17-32-28(3)40(60)55-35(45(65)66)18-19-39(59)57(6)30(5)42(62)51-29(4)41(61)54-34(20-22-72(8,69)70)44(64)56-36(46(67)68)25-38(58)52-33(43(63)53-32)15-12-21-50-47(48)49/h9-11,13-14,16-17,23,27-29,32-37H,5,12,15,18-22,24-25H2,1-4,6-8H3,(H,51,62)(H,52,58)(H,53,63)(H,54,61)(H,55,60)(H,56,64)(H,65,66)(H,67,68)(H4,48,49,50)/b17-16+,26-23+/t27-,28-,29+,32-,33-,34-,35+,36+,37-/m0/s1",OKBMXOMXWWVSNC-QTDAUVDESA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-(3-sulfinopropyl)-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684784,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,"MS2 available in the article, thiol derivatization and S-oxidation used."
CyanoMetDB_1936,"[D-Asp3,Dha7]MC-HtyR",,,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(NC(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C51H70N10O13/c1-28(25-29(2)41(74-6)26-34-11-8-7-9-12-34)14-20-36-30(3)44(65)60-39(49(70)71)22-23-42(63)55-31(4)45(66)56-32(5)46(67)59-38(21-17-33-15-18-35(62)19-16-33)48(69)61-40(50(72)73)27-43(64)57-37(47(68)58-36)13-10-24-54-51(52)53/h7-9,11-12,14-16,18-20,25,29-30,32,36-41,62H,4,10,13,17,21-24,26-27H2,1-3,5-6H3,(H,55,63)(H,56,66)(H,57,64)(H,58,68)(H,59,67)(H,60,65)(H,61,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-14+,28-25+/t29-,30-,32+,36-,37-,38-,39+,40+,41-/m0/s1",HNBGKQBQBJXYNW-MRZPJGPASA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683850,,10.1021/tx00029a011,https://pubs.acs.org/doi/abs/10.1021/tx00029a011,"Structures of three new homotyrosine-containing microcystins and a new homophenylalanine variant from Anabaena sp. strain 66;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a011;Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Carmichael, Wayne W.; Rouhiainen, Leo; Luukkainen, Raija; Rinehart, Kenneth L.",Anabaena,n.a.,[Anabaena sp.]66,,Stereochemistry defined by chiral GC-MS analyses.
CyanoMetDB_1937,[D-Asp3]MC-YR,,,Microcystin,C51H70N10O13,1031.16,1030.512383,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H70N10O13/c1-28(24-29(2)41(74-7)26-33-12-9-8-10-13-33)15-20-36-30(3)44(65)58-38(49(70)71)21-22-43(64)61(6)32(5)46(67)55-31(4)45(66)59-39(25-34-16-18-35(62)19-17-34)48(69)60-40(50(72)73)27-42(63)56-37(47(68)57-36)14-11-23-54-51(52)53/h8-10,12-13,15-20,24,29-31,36-41,62H,5,11,14,21-23,25-27H2,1-4,6-7H3,(H,55,67)(H,56,63)(H,57,68)(H,58,65)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,28-24+/t29-,30-,31+,36-,37-,38+,39-,40+,41-/m0/s1",QZMBFAWAEGLVMI-XAIZWMDNSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101642890,,10.1016/0041-0101(92)90523-8,https://linkinghub.elsevier.com/retrieve/pii/0041010192905238,"Isolation and structures of microcystins from a cyanobacterial water bloom (Finland);Toxicon;30;11;;1992;journalArticle;10.1016/0041-0101(92)90523-8;Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Sun, Furong; Carmichael, Wayne W.; Rinehart, Kenneth L.",n.a.,n.a.,n.a.,"field sample, artificial lake serving as a drinking water reservoir for two small cities, Raisio and Naantah (southwestern Finland) Microcystis aeruginosa, Aphanizomenon flos aquae","Water bloom sample collected from an artificial lake serving as a drinking water reservoir for two small cities, Raisio and Naantah (southwestern Finland). The bloom consisted of equal amounts of planktonic Microcystis aerughwsa and Aphanizomenon flos-aquae. Stereochemistry assumed based on other MC congeners."
CyanoMetDB_1938,[Dha7]MC-YR,,,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(NC(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C51H70N10O13/c1-27(24-28(2)40(74-7)26-33-12-9-8-10-13-33)15-20-36-29(3)43(64)59-38(49(70)71)21-22-41(63)55-31(5)45(66)56-32(6)46(67)60-39(25-34-16-18-35(62)19-17-34)48(69)61-42(50(72)73)30(4)44(65)58-37(47(68)57-36)14-11-23-54-51(52)53/h8-10,12-13,15-20,24,28-30,32,36-40,42,62H,5,11,14,21-23,25-26H2,1-4,6-7H3,(H,55,63)(H,56,66)(H,57,68)(H,58,65)(H,59,64)(H,60,67)(H,61,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,27-24+/t28-,29-,30-,32+,36-,37-,38+,39-,40-,42+/m0/s1",IRVUYTLKKQEENF-YMOIXCTBSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101643556,,10.1016/0041-0101(92)90524-9,https://linkinghub.elsevier.com/retrieve/pii/0041010192905249,"Isolation and structures of five microcystins from a Russian Microcystis aeruginosa strain CALU 972;Toxicon;30;11;;1992;journalArticle;10.1016/0041-0101(92)90524-9;Sivonen, Kaarina; Namikoshi, Michio; Evans, William R.; Gromov, Boris V.; Carmichael, Wayne W.; Rinehart, Kenneth L.",Microcystis,aeruginosa,[Microcystis aeruginosa]CALU 972,,
CyanoMetDB_1939,[DMAdda5]MC‐YR,,,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C51H70N10O13/c1-27(24-28(2)40(63)26-33-12-9-8-10-13-33)15-20-36-29(3)43(65)58-38(49(71)72)21-22-41(64)61(7)32(6)46(68)55-31(5)45(67)59-39(25-34-16-18-35(62)19-17-34)48(70)60-42(50(73)74)30(4)44(66)57-37(47(69)56-36)14-11-23-54-51(52)53/h8-10,12-13,15-20,24,28-31,36-40,42,62-63H,6,11,14,21-23,25-26H2,1-5,7H3,(H,55,68)(H,56,69)(H,57,66)(H,58,65)(H,59,67)(H,60,70)(H,71,72)(H,73,74)(H4,52,53,54)/b20-15+,27-24+/t28-,29-,30-,31+,36-,37-,38+,39-,40-,42+/m0/s1",WZIFCFVNRWFPIQ-GAOADQHISA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-(4-hydroxybenzyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802406,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,n.a.,AB2011/53 (isolated from Hartbeespoort Dam),,MS2 available in the article
CyanoMetDB_1940,"[D-Asp3,DMAdda5]MC‐HtyR",,,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C51H70N10O13/c1-28(25-29(2)41(63)26-34-11-8-7-9-12-34)14-20-36-30(3)44(66)59-39(49(71)72)22-23-43(65)61(6)32(5)46(68)55-31(4)45(67)58-38(21-17-33-15-18-35(62)19-16-33)48(70)60-40(50(73)74)27-42(64)56-37(47(69)57-36)13-10-24-54-51(52)53/h7-9,11-12,14-16,18-20,25,29-31,36-41,62-63H,5,10,13,17,21-24,26-27H2,1-4,6H3,(H,55,68)(H,56,64)(H,57,69)(H,58,67)(H,59,66)(H,60,70)(H,71,72)(H,73,74)(H4,52,53,54)/b20-14+,28-25+/t29-,30-,31+,36-,37-,38-,39+,40+,41-/m0/s1",BMYLDJWLCUBHCY-SMHKPUPISA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-(4-hydroxyphenethyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683867,,10.1007/s00203-004-0711-3,http://link.springer.com/10.1007/s00203-004-0711-3,"Diversity of coexisting Planktothrix (Cyanobacteria) chemotypes deduced by mass spectral analysis of microystins and other oligopeptides;Archives of Microbiology;182;4;;2004;journalArticle;10.1007/s00203-004-0711-3;Welker, Martin; Christiansen, Guntram; von Döhren, Hans",Planktothrix,sp.,[Planktothrix sp.]Max06,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1941,[D-Asp3]MC-RR,,,Microcystin,C48H73N13O12,1024.17,1023.550165,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H73N13O12/c1-26(23-27(2)37(73-7)24-31-13-9-8-10-14-31)17-18-32-28(3)40(64)59-35(45(69)70)19-20-39(63)61(6)30(5)42(66)55-29(4)41(65)58-34(16-12-22-54-48(51)52)44(68)60-36(46(71)72)25-38(62)56-33(43(67)57-32)15-11-21-53-47(49)50/h8-10,13-14,17-18,23,27-29,32-37H,5,11-12,15-16,19-22,24-25H2,1-4,6-7H3,(H,55,66)(H,56,62)(H,57,67)(H,58,65)(H,59,64)(H,60,68)(H,69,70)(H,71,72)(H4,49,50,53)(H4,51,52,54)/b18-17+,26-23+/t27-,28-,29+,32-,33-,34-,35+,36+,37-/m0/s1",UNKUVURYGRFCIZ-LTPNNWFFSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",21576447,,10.1016/0041-0101(89)90153-0,https://linkinghub.elsevier.com/retrieve/pii/0041010189901530,"Structure and toxicity of a peptide hepatotoxin from the cyanobacterium Oscillatoria agardhii;Toxicon;27;9;;1989;journalArticle;10.1016/0041-0101(89)90153-0;Meriluoto, J.A.O.; Sandström, A.; Eriksson, J.E.; Remaud, G.; Grey Graig, A.; Chattopadhyaya, J.",Oscillatoria/Planktothrix,agardhii,[Oscillatoria/Planktothrix agardhii]CYA-29,,Stereochemistry not defined in Meriluoto reference. Subsequent work by Namikoshi et al established stereochemistry; [Meriluoto 1989] Planktothrix/Oscillatoria agardhii CYA-29
CyanoMetDB_1942,[Dha7]MC‐RY,,Microcystin[DAsp3]RR,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(NC(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C51H70N10O13/c1-27(24-28(2)40(74-7)26-33-12-9-8-10-13-33)15-20-36-29(3)43(64)59-38(49(70)71)21-22-41(63)55-31(5)45(66)56-32(6)46(67)58-37(14-11-23-54-51(52)53)47(68)61-42(50(72)73)30(4)44(65)60-39(48(69)57-36)25-34-16-18-35(62)19-17-34/h8-10,12-13,15-20,24,28-30,32,36-40,42,62H,5,11,14,21-23,25-26H2,1-4,6-7H3,(H,55,63)(H,56,66)(H,57,69)(H,58,67)(H,59,64)(H,60,65)(H,61,68)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,27-24+/t28-,29-,30-,32+,36-,37-,38+,39-,40-,42+/m0/s1",GEDLVCGECHWHFL-YMOIXCTBSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(3-guanidinopropyl)-15-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684758,DTXSID201016195,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry assumed based on other MC congeners. Microcystin-containing cyanobacterial bloom samples (20 L) from Mwanza Gulf in Lake Victoria, Tanzania, in 2010. MS2 available in the article"
CyanoMetDB_1943,"[D-Asp³,Dhb7]MC‐RY",,,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)NC([C@H](CC2=CC=C(O)C=C2)NC(C[C@H](C(O)=O)NC([C@@H](N3)CCCNC(N)=N)=O)=O)=O)=O)NC(C(N[C@@H](C3=O)C)=O)=CC,"InChI=1S/C51H70N10O13/c1-7-35-46(67)55-31(5)45(66)59-37(14-11-23-54-51(52)53)47(68)61-40(50(72)73)27-43(64)57-39(25-33-16-18-34(62)19-17-33)48(69)58-36(30(4)44(65)60-38(49(70)71)21-22-42(63)56-35)20-15-28(2)24-29(3)41(74-6)26-32-12-9-8-10-13-32/h7-10,12-13,15-20,24,29-31,36-41,62H,11,14,21-23,25-27H2,1-6H3,(H,55,67)(H,56,63)(H,57,64)(H,58,69)(H,59,66)(H,60,65)(H,61,68)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,28-24+,35-7?/t29-,30-,31+,36-,37-,38+,39-,40+,41-/m0/s1",VLFZRTCMEIPKAG-DWHNULMMSA-N,"(E)-8-(3-((diaminomethylene)amino)propyl)-2-ethylidene-15-(4-hydroxybenzyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684752,,10.1021/es305202p,https://pubs.acs.org/doi/10.1021/es305202p,"LC-MS Analysis with Thiol Derivatization to Differentiate [Dhb 7 ]- from [Mdha 7 ]-Microcystins: Analysis of Cyanobacterial Blooms, Planktothrix Cultures and European Crayfish from Lake Steinsfjorden, Norway;Environmental Science & Technology;47;9;;2013;journalArticle;10.1021/es305202p;Miles, Christopher O.; Sandvik, Morten; Haande, Sigrid; Nonga, Hezron; Ballot, Andreas",n.a.,n.a.,multiple strains,"field sample, containing Oscillatoria agardhii ; Planktothrix rubescens","Detected in a concentrated phytoplankton sample derived from a net sample (25 μm mesh) taken from L. Steinsfjorden, Norway. MS2 available in the article"
CyanoMetDB_1944,"[D-Asp3,(E)-Dhb7]MC-YR","[Asp3, (E)‐Dhb7]MC‐YR",,Microcystin,C51H70N10O13,1031.16,1030.512383,O=C(N/C(C(N[C@@H](C1=O)C)=O)=C/C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C51H70N10O13/c1-7-35-46(67)55-31(5)45(66)60-39(25-33-16-18-34(62)19-17-33)48(69)61-40(50(72)73)27-43(64)57-37(14-11-23-54-51(52)53)47(68)58-36(30(4)44(65)59-38(49(70)71)21-22-42(63)56-35)20-15-28(2)24-29(3)41(74-6)26-32-12-9-8-10-13-32/h7-10,12-13,15-20,24,29-31,36-41,62H,11,14,21-23,25-27H2,1-6H3,(H,55,67)(H,56,63)(H,57,64)(H,58,68)(H,59,65)(H,60,66)(H,61,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,28-24+,35-7+/t29-,30-,31+,36-,37-,38+,39-,40+,41-/m0/s1",HCSRXVAEHOQWBK-RYYUPNNBSA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683830,,10.1371/journal.pone.0091476,https://dx.plos.org/10.1371/journal.pone.0091476,"Selectivity and Potency of Microcystin Congeners against OATP1B1 and OATP1B3 Expressing Cancer Cells;PLoS ONE;9;3;;2014;journalArticle;10.1371/journal.pone.0091476;Niedermeyer, Timo H. J.; Daily, Abigail; Swiatecka-Hagenbruch, Monika; Moscow, Jeffrey A.",Oscillatoria/Planktothrix,rubescens,[Oscillatoria/Planktothrix rubescens]CBT 310,,Stereochemistry determined by 2D-NMR.
CyanoMetDB_1945,MC‐LY(OMe),,,Microcystin,C53H73N7O14,1032.19,1031.52155,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC(OC)=C(O)C=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C53H73N7O14/c1-28(2)23-39-51(68)59-45(53(71)72)32(6)47(64)57-40(25-36-18-21-41(61)43(27-36)74-11)50(67)55-37(19-17-29(3)24-30(4)42(73-10)26-35-15-13-12-14-16-35)31(5)46(63)56-38(52(69)70)20-22-44(62)60(9)34(8)49(66)54-33(7)48(65)58-39/h12-19,21,24,27-28,30-33,37-40,42,45,61H,8,20,22-23,25-26H2,1-7,9-11H3,(H,54,66)(H,55,67)(H,56,63)(H,57,64)(H,58,65)(H,59,68)(H,69,70)(H,71,72)/b19-17+,29-24+/t30-,31-,32-,33+,37-,38+,39-,40-,42-,45+/m0/s1",QARMBORJLOKVDT-PWMZSGMGSA-N,"3-(4-hydroxybenzyl)-21-isobutyl-6-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-7,14,18,25-tetramethyl-15-methylene-4,8,13,16,19,22,26-heptaoxo-1-oxa-2,5,9,14,17,20,23-heptaazacycloheptacosane-10,24-dicarboxylic acid",155802277,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,CYA548,,Stereochemistry assumed based on other MC congeners. Location of OCH2 on Tyr not confirmed
CyanoMetDB_1946,[D-Asp3]MC-(H2)YR,,,Microcystin,C51H72N10O13,1033.19,1032.528032,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC3=CC[C@@H](O)C=C3)=O)=O)=O)=O,"InChI=1S/C51H72N10O13/c1-28(24-29(2)41(74-7)26-33-12-9-8-10-13-33)15-20-36-30(3)44(65)58-38(49(70)71)21-22-43(64)61(6)32(5)46(67)55-31(4)45(66)59-39(25-34-16-18-35(62)19-17-34)48(69)60-40(50(72)73)27-42(63)56-37(47(68)57-36)14-11-23-54-51(52)53/h8-10,12-13,15-18,20,24,29-31,35-41,62H,5,11,14,19,21-23,25-27H2,1-4,6-7H3,(H,55,67)(H,56,63)(H,57,68)(H,58,65)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,28-24+/t29-,30-,31+,35-,36-,37-,38+,39-,40+,41-/m0/s1",CJOJWAGHCMFLCT-PYVADERCSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(((R)-4-hydroxycyclohexa-1,5-dien-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684956,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,"Thiol derivatization, stereochemistry assumed, including (H2)Y from Crawford et al. (2011) and Parker et al. (2012)"
CyanoMetDB_1947,[Dha7]MC‐(H4)YR,,,Microcystin,C51H74N10O13,1035.19,1034.543683,O=C(CC[C@@H](NC([C@H]([C@@H](NC([C@@H](NC([C@H]([C@@H](NC([C@H](C[C@]1(C=C[C@@H](CC1)O)[H])N2)=O)C(O)=O)C)=O)CCCNC(N)=N)=O)/C=C/C(C)=C/[C@@H]([C@H](CC3=CC=CC=C3)OC)C)C)=O)C(O)=O)NC(C(N[C@H](C)C2=O)=O)=C,"InChI=1S/C51H74N10O13/c1-27(24-28(2)40(74-7)26-33-12-9-8-10-13-33)15-20-36-29(3)43(64)59-38(49(70)71)21-22-41(63)55-31(5)45(66)56-32(6)46(67)60-39(25-34-16-18-35(62)19-17-34)48(69)61-42(50(72)73)30(4)44(65)58-37(47(68)57-36)14-11-23-54-51(52)53/h8-10,12-13,15-16,18,20,24,28-30,32,34-40,42,62H,5,11,14,17,19,21-23,25-26H2,1-4,6-7H3,(H,55,63)(H,56,66)(H,57,68)(H,58,65)(H,59,64)(H,60,67)(H,61,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,27-24+/t28-,29-,30-,32+,34-,35-,36-,37-,38+,39-,40-,42+/m0/s1",TUAADMHCVHCCPV-UIBXFZKZSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684735,,10.1007/s00216-008-2040-x,http://link.springer.com/10.1007/s00216-008-2040-x,"NIES certified reference material for microcystins, hepatotoxic cyclic peptide toxins from cyanobacterial blooms in eutrophic water bodies;Analytical and Bioanalytical Chemistry;391;6;;2008;journalArticle;10.1007/s00216-008-2040-x;Sano, Tomoharu; Takagi, Hiroo; Nishikawa, Masataka; Kaya, Kunimitsu",Microcystis,aeruginosa,[Microcystis aeruginosa]NIES CRM No. 26,,Comprehensive analysis applied for characterisation.
CyanoMetDB_1948,[D-Asp³]MC‐(H4)YR,,,Microcystin,C51H74N10O13,1035.21,1034.543683,O=C(CC[C@@H](NC([C@H]([C@@H](NC([C@@H](NC(C[C@@H](NC([C@H](C[C@]1(C=C[C@@H](CC1)O)[H])N2)=O)C(O)=O)=O)CCCNC(N)=N)=O)/C=C/C(C)=C/[C@@H]([C@H](CC3=CC=CC=C3)OC)C)C)=O)C(O)=O)N(C(C(N[C@H](C)C2=O)=O)=C)C,"InChI=1S/C51H74N10O13/c1-28(24-29(2)41(74-7)26-33-12-9-8-10-13-33)15-20-36-30(3)44(65)58-38(49(70)71)21-22-43(64)61(6)32(5)46(67)55-31(4)45(66)59-39(25-34-16-18-35(62)19-17-34)48(69)60-40(50(72)73)27-42(63)56-37(47(68)57-36)14-11-23-54-51(52)53/h8-10,12-13,15-16,18,20,24,29-31,34-41,62H,5,11,14,17,19,21-23,25-27H2,1-4,6-7H3,(H,55,67)(H,56,63)(H,57,68)(H,58,65)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-15+,28-24+/t29-,30-,31+,34-,35-,36-,37-,38+,39-,40+,41-/m0/s1",JAXVACFEWWEOKE-NMOCKCCNSA-N,"15-(3-((diaminomethylene)amino)propyl)-8-((4-hydroxycyclohex-1-en-1-yl)methyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802127,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,aeruginosa,AB2011/53,,"MS2 available in the article, thiol derivatization too. HRMS/MS in Miller et al. (accepted)"
CyanoMetDB_1949,[DMAdda5]MC‐(H4)YR,,,Microcystin,C51H74N10O13,1035.19,1034.543683,O=C(CC[C@@H](NC([C@H]([C@@H](NC([C@@H](NC([C@H]([C@@H](NC([C@H](C[C@]1(C=C[C@@H](CC1)O)[H])N2)=O)C(O)=O)C)=O)CCCNC(N)=N)=O)/C=C/C(C)=C/[C@@H]([C@H](CC3=CC=CC=C3)O)C)C)=O)C(O)=O)N(C(C(N[C@H](C)C2=O)=O)=C)C,"InChI=1S/C51H74N10O13/c1-27(24-28(2)40(63)26-33-12-9-8-10-13-33)15-20-36-29(3)43(65)58-38(49(71)72)21-22-41(64)61(7)32(6)46(68)55-31(5)45(67)59-39(25-34-16-18-35(62)19-17-34)48(70)60-42(50(73)74)30(4)44(66)57-37(47(69)56-36)14-11-23-54-51(52)53/h8-10,12-13,15-16,18,20,24,28-31,34-40,42,62-63H,6,11,14,17,19,21-23,25-26H2,1-5,7H3,(H,55,68)(H,56,69)(H,57,66)(H,58,65)(H,59,67)(H,60,70)(H,71,72)(H,73,74)(H4,52,53,54)/b20-15+,27-24+/t28-,29-,30-,31+,34-,35-,36-,37-,38+,39-,40-,42+/m0/s1",LWTYIWMPGBPRGQ-ZVRPPTPOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684739,,10.1094/MPMI-22-6-0695,http://apsjournals.apsnet.org/doi/10.1094/MPMI-22-6-0695,"Microcystin Production in the Tripartite Cyanolichen Peltigera leucophlebia;Molecular Plant-Microbe Interactions;22;6;;2009;journalArticle;10.1094/MPMI-22-6-0695;Kaasalainen, Ulla; Jokela, Jouni; Fewer, David P.; Sivonen, Kaarina; Rikkinen, Jouko",Nostoc,sp.,[Nostoc sp.]UK18,,Stereochemistry inferred based on other MC congeners. Position of hydrogen in (H4)Y is assumed based on Parker et al. 2012.
CyanoMetDB_1950,"[D-Asp3,Dha7]MC-LR",,,Microcystin,C47H70N10O12,967.12,966.517468,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C47H70N10O12/c1-25(2)21-35-44(64)57-36(46(67)68)24-39(59)53-33(15-12-20-50-47(48)49)43(63)54-32(17-16-26(3)22-27(4)37(69-8)23-31-13-10-9-11-14-31)28(5)40(60)55-34(45(65)66)18-19-38(58)51-29(6)41(61)52-30(7)42(62)56-35/h9-11,13-14,16-17,22,25,27-28,30,32-37H,6,12,15,18-21,23-24H2,1-5,7-8H3,(H,51,58)(H,52,61)(H,53,59)(H,54,63)(H,55,60)(H,56,62)(H,57,64)(H,65,66)(H,67,68)(H4,48,49,50)/b17-16+,26-22+/t27-,28-,30+,32-,33-,34+,35-,36+,37-/m0/s1",PENYTKSZIDPONS-NGLWDUFTSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6441615,,10.1016/0041-0101(91)90022-J,https://linkinghub.elsevier.com/retrieve/pii/004101019190022J,"Isolation of two toxic heptapeptide microcystins from an axenic strain of Microcystis aeruginosa, K-139;Toxicon;29;43955;;1991;journalArticle;10.1016/0041-0101(91)90022-J;Harada, Ken-ichi; Ogawa, Kiyoshi; Matsuura, Kenji; Nagai, Hidetoshi; Murata, Hideaki; Suzuki, Makoto; Itezono, Yoshiko; Nakayama, Noboru; Shirai, Makoto; Nakano, Masayasu",Microcystis,aeruginosa,[Microcystis aeruginosa]K-139,,Reported by Harada et al. 1992 but insufficient quantity of available for in depth characterisation.
CyanoMetDB_1951,[ADMAdda5]MC-LHar,,,Microcystin,C51H76N10O13,1037.21,1036.559333,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C51H76N10O13/c1-27(2)24-39-48(69)60-42(50(72)73)31(6)44(65)57-37(18-14-15-23-54-51(52)53)47(68)56-36(20-19-28(3)25-29(4)40(74-34(9)62)26-35-16-12-11-13-17-35)30(5)43(64)58-38(49(70)71)21-22-41(63)61(10)33(8)46(67)55-32(7)45(66)59-39/h11-13,16-17,19-20,25,27,29-32,36-40,42H,8,14-15,18,21-24,26H2,1-7,9-10H3,(H,55,67)(H,56,68)(H,57,65)(H,58,64)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-19+,28-25+/t29-,30-,31-,32+,36-,37-,38+,39-,40-,42+/m0/s1",HSOIUAGRQAPKJZ-PMZUZRGZSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-8-isobutyl-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",14752802,,10.1021/jo00312a019,https://pubs.acs.org/doi/abs/10.1021/jo00312a019,"Structures of three new cyclic heptapeptide hepatotoxins produced by the cyanobacterium (blue-green alga) Nostoc sp. strain 152;The Journal of Organic Chemistry;55;25;;1990;journalArticle;10.1021/jo00312a019;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Sivonen, Kaarina; Carmichael, Wayne W.",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry well defined using complementary techniques.
CyanoMetDB_1952,[ADMAdda5]MC‐HilR,,,Microcystin,C51H76N10O13,1037.21,1036.559333,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C[C@@H](C)CC)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C51H76N10O13/c1-11-27(2)25-39-48(69)60-42(50(72)73)31(6)44(65)57-37(18-15-23-54-51(52)53)47(68)56-36(20-19-28(3)24-29(4)40(74-34(9)62)26-35-16-13-12-14-17-35)30(5)43(64)58-38(49(70)71)21-22-41(63)61(10)33(8)46(67)55-32(7)45(66)59-39/h12-14,16-17,19-20,24,27,29-32,36-40,42H,8,11,15,18,21-23,25-26H2,1-7,9-10H3,(H,55,67)(H,56,68)(H,57,65)(H,58,64)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b20-19+,28-24+/t27-,29-,30-,31-,32+,36-,37-,38+,39-,40-,42+/m0/s1",SJPOBNMEGAYSAV-XZKVJARFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-1,5,12,19-tetramethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684730,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1953,[D-Asp3]MC-LR,3-desmethylmicrocystin LR,,Microcystin,C48H72N10O12,981.15,980.5331181,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H72N10O12/c1-26(2)22-36-45(65)57-37(47(68)69)25-39(59)53-34(16-13-21-51-48(49)50)44(64)54-33(18-17-27(3)23-28(4)38(70-9)24-32-14-11-10-12-15-32)29(5)41(61)55-35(46(66)67)19-20-40(60)58(8)31(7)43(63)52-30(6)42(62)56-36/h10-12,14-15,17-18,23,26,28-30,33-38H,7,13,16,19-22,24-25H2,1-6,8-9H3,(H,52,63)(H,53,59)(H,54,64)(H,55,61)(H,56,62)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,27-23+/t28-,29-,30+,33-,34-,35+,36-,37+,38-/m0/s1",VYEBKSHVYPDMQQ-MREVJOSWSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6440025,,10.1073/pnas.86.3.770,http://www.pnas.org/cgi/doi/10.1073/pnas.86.3.770,"Structural characterization of toxic cyclic peptides from blue-green algae by tandem mass spectrometry.;Proceedings of the National Academy of Sciences;86;3;;1989;journalArticle;10.1073/pnas.86.3.770;Krishnamurthy, T.; Szafraniec, L.; Hunt, D. F.; Shabanowitz, J.; Yates, J. R.; Hauer, C. R.; Carmichael, W. W.; Skulberg, O.; Codd, G. A.; Missler, S.",Anabaena,flos aquae,[Anabaena flos-aquae]S-23-g-1,,Stereochemistry based on chemical derivatisation of amino acids hydrolysed from parent compound.
CyanoMetDB_1954,MC‐AnaR,,Microcystin[DAsp3]LR,Microcystin,C52H80N10O12,1037.27,1036.595718,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCCCCC)=O)=O)=O)=O,"InChI=1S/C52H80N10O12/c1-10-11-12-13-17-21-38-49(69)61-43(51(72)73)33(5)45(65)58-39(22-18-27-55-52(53)54)48(68)57-37(24-23-30(2)28-31(3)41(74-9)29-36-19-15-14-16-20-36)32(4)44(64)60-40(50(70)71)25-26-42(63)62(8)35(7)47(67)56-34(6)46(66)59-38/h14-16,19-20,23-24,28,31-34,37-41,43H,7,10-13,17-18,21-22,25-27,29H2,1-6,8-9H3,(H,56,67)(H,57,68)(H,58,65)(H,59,66)(H,60,64)(H,61,69)(H,70,71)(H,72,73)(H4,53,54,55)/b24-23+,30-28+/t31-,32-,33-,34+,37-,38-,39-,40+,41-,43+/m0/s1",MKFNFTJHXRTWHG-LFTVSPSXSA-N,"15-(3-((diaminomethylene)amino)propyl)-8-heptyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802192,DTXSID501016182,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,n.a.,AB2011/53,,"Thiol derivatization, MS/MS. Stereochemistry of Ana (i.e. no branching) is assumed since cannot be distinguished by MS/MS"
CyanoMetDB_1955,[D-Asp³]MC‐YY,,,Microcystin,C54H67N7O14,1038.15,1037.4746,O=C(CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)NC([C@H](CC2=CC=C(O)C=C2)NC(C[C@H](C(O)=O)NC([C@@H](N3)CC4=CC=C(O)C=C4)=O)=O)=O)=O)N(C)C(C(N[C@@H](C3=O)C)=O)=C,"InChI=1S/C54H67N7O14/c1-30(25-31(2)45(75-7)28-35-11-9-8-10-12-35)13-22-40-32(3)48(66)58-41(53(71)72)23-24-47(65)61(6)34(5)50(68)55-33(4)49(67)59-43(27-37-16-20-39(63)21-17-37)52(70)60-44(54(73)74)29-46(64)56-42(51(69)57-40)26-36-14-18-38(62)19-15-36/h8-22,25,31-33,40-45,62-63H,5,23-24,26-29H2,1-4,6-7H3,(H,55,68)(H,56,64)(H,57,69)(H,58,66)(H,59,67)(H,60,70)(H,71,72)(H,73,74)/b22-13+,30-25+/t31-,32-,33+,40-,41+,42-,43-,44+,45-/m0/s1",OCYZRCVDCXSNRA-JFMOJRJTSA-N,"8,15-bis(4-hydroxybenzyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802239,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,CYA548,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1956,"[Gly1,D-Asp3,ADMAdda5,Dhb7]MC-RR",,,Microcystin,C48H71N13O13,1038.16,1037.52943,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)C(=CC)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)CCCNC(=N)N,"InChI=1S/C48H71N13O13/c1-6-31-42(67)55-25-40(65)58-34(15-11-21-54-48(51)52)44(69)61-36(46(72)73)24-39(64)57-33(14-10-20-53-47(49)50)43(68)59-32(28(4)41(66)60-35(45(70)71)18-19-38(63)56-31)17-16-26(2)22-27(3)37(74-29(5)62)23-30-12-8-7-9-13-30/h6-9,12-13,16-17,22,27-28,32-37H,10-11,14-15,18-21,23-25H2,1-5H3,(H,55,67)(H,56,63)(H,57,64)(H,58,65)(H,59,68)(H,60,66)(H,61,69)(H,70,71)(H,72,73)(H4,49,50,53)(H4,51,52,54)/b17-16+,26-22+,31-6?/t27-,28-,32-,33-,34-,35+,36+,37-/m0/s1",KSYULEJYRAZDKO-DKIRLTFKSA-N,"(8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-2-ethylidene-8,15-bis(3-guanidinopropyl)-19-methyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683805,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)",From Antarctica. Stereochemistry partially defined by advanced Marfey amino acid analysis
CyanoMetDB_1957,"[Gly1,D-Asp3,ADMAdda5]MC-RR",,,Microcystin,C48H71N13O13,1038.16,1037.52943,O=C(N(C)C(C(NCC1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C48H71N13O13/c1-26(22-27(2)37(74-30(5)62)23-31-12-8-7-9-13-31)16-17-32-28(3)41(66)59-35(45(70)71)18-19-40(65)61(6)29(4)42(67)55-25-39(64)57-34(15-11-21-54-48(51)52)44(69)60-36(46(72)73)24-38(63)56-33(43(68)58-32)14-10-20-53-47(49)50/h7-9,12-13,16-17,22,27-28,32-37H,4,10-11,14-15,18-21,23-25H2,1-3,5-6H3,(H,55,67)(H,56,63)(H,57,64)(H,58,68)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,49,50,53)(H4,51,52,54)/b17-16+,26-22+/t27-,28-,32-,33-,34-,35+,36+,37-/m0/s1",UBDNPCAZTHQJTO-KTRJARRNSA-N,"(8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8,15-bis(3-guanidinopropyl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683838,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",Nostoc,cyanobacterial mat,n.a.,,From Antarctica. Compound MC-6 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1958,[D-Asp3]MC-RHar,,,Microcystin,C49H75N13O12,1038.2,1037.565815,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C49H75N13O12/c1-27(24-28(2)38(74-7)25-32-14-9-8-10-15-32)18-19-33-29(3)41(65)60-36(46(70)71)20-21-40(64)62(6)31(5)43(67)56-30(4)42(66)59-35(17-13-23-55-49(52)53)45(69)61-37(47(72)73)26-39(63)57-34(44(68)58-33)16-11-12-22-54-48(50)51/h8-10,14-15,18-19,24,28-30,33-38H,5,11-13,16-17,20-23,25-26H2,1-4,6-7H3,(H,56,67)(H,57,63)(H,58,68)(H,59,66)(H,60,65)(H,61,69)(H,70,71)(H,72,73)(H4,50,51,54)(H4,52,53,55)/b19-18+,27-24+/t28-,29-,30+,33-,34-,35-,36+,37+,38-/m0/s1",PNAKPAPXVBSBCP-ZFXYJWGJSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(4-guanidinobutyl)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683807,,10.3390/toxins11110619,https://www.mdpi.com/2072-6651/11/11/619,"A Data-Independent Methodology for the Structural Characterization of Microcystins and Anabaenopeptins Leading to the Identification of Four New Congeners;Toxins;11;11;;2019;journalArticle;10.3390/toxins11110619;Roy-Lachapelle, Audrey; Solliec, Morgan; Sauvé, Sébastien; Gagnon, Christian",n.a.,n.a.,n.a.,"field samples, blooms located in Canada, United Kingdom and France",
CyanoMetDB_1959,"[D-Asp3,D-MeO-Glu6]MC-RR","[D-Asp3,D-Glu(OMe)6]MC-RR",,Microcystin,C49H75N13O12,1038.2,1037.565815,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C49H75N13O12/c1-27(24-28(2)38(73-7)25-32-14-10-9-11-15-32)18-19-33-29(3)41(65)60-36(47(72)74-8)20-21-40(64)62(6)31(5)43(67)56-30(4)42(66)59-35(17-13-23-55-49(52)53)45(69)61-37(46(70)71)26-39(63)57-34(44(68)58-33)16-12-22-54-48(50)51/h9-11,14-15,18-19,24,28-30,33-38H,5,12-13,16-17,20-23,25-26H2,1-4,6-8H3,(H,56,67)(H,57,63)(H,58,68)(H,59,66)(H,60,65)(H,61,69)(H,70,71)(H4,50,51,54)(H4,52,53,55)/b19-18+,27-24+/t28-,29-,30+,33-,34-,35-,36+,37+,38-/m0/s1",DHJZAIAJHLMMPF-ZFXYJWGJSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",23248162,,10.1021/np034036r,https://pubs.acs.org/doi/10.1021/np034036r,"Seco[d-Asp3]microcystin-RR and [d-Asp3,d-Glu(OMe)6]microcystin-RR, Two New Microcystins from a Toxic Water Bloom of the Cyanobacterium Planktothrix rubescens;Journal of Natural Products;67;3;;2004;journalArticle;10.1021/np034036r;Grach-Pogrebinsky, Olga; Sedmak, Bojan; Carmeli, Shmuel",n.a.,rubescens,n.a.,"field sample, Planktothrix","Isolated from a Planktothrix rubescens toxic bloom collected in Lake Bled, Slovenia. Cited reference stresses that due to isolation of insufficient material, the structure is not definitively defined. MS2 spectra were used to elucidate the location of the methyl group on the glutamic acid moiety. Stereochemistry inferred from the similarity of Marfey reagent reaction with other cyanopeptides isolated in the same paper, for which more material was available and thus, 2D-NMR performed."
CyanoMetDB_1961,"[Asp3,Dhb7]MC-LY","[Asp3,Dhb7]MC‐LY",,Microcystin,C51H69N7O13,988.13,987.4953356,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H69N7O13/c1-9-36-47(64)52-32(7)46(63)57-39(23-28(2)3)48(65)58-41(51(69)70)27-44(61)54-40(25-34-16-18-35(59)19-17-34)49(66)55-37(31(6)45(62)56-38(50(67)68)21-22-43(60)53-36)20-15-29(4)24-30(5)42(71-8)26-33-13-11-10-12-14-33/h9-20,24,28,30-32,37-42,59H,21-23,25-27H2,1-8H3,(H,52,64)(H,53,60)(H,54,61)(H,55,66)(H,56,62)(H,57,63)(H,58,65)(H,67,68)(H,69,70)/b20-15+,29-24+,36-9?/t30-,31-,32+,37-,38+,39-,40-,41+,42-/m0/s1",OSIYJQIKKULRMP-MNXMRTDASA-N,"(E)-2-ethylidene-15-(4-hydroxybenzyl)-8-isobutyl-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",,,10.1021/es305202p,https://pubs.acs.org/doi/10.1021/es305202p,"LC-MS Analysis with Thiol Derivatization to Differentiate [Dhb 7 ]- from [Mdha 7 ]-Microcystins: Analysis of Cyanobacterial Blooms, Planktothrix Cultures and European Crayfish from Lake Steinsfjorden, Norway;Environmental Science & Technology;47;9;;2013;journalArticle;10.1021/es305202p;Miles, Christopher O.; Sandvik, Morten; Haande, Sigrid; Nonga, Hezron; Ballot, Andreas",Oscillatoria/Planktothrix,rubescens,n.a.,,"Detected in a concentrated phytoplankton sample derived from a net sample (25 μm mesh) taken from L. Steinsfjorden, Norway - Planktothrix agardhii was reported as major species in epilimnion (0-7 m), but was only moderately abundant in the metalimnion (8-14 m). Stereochemistry assumed based on other MC congeners."
CyanoMetDB_1962,"[D-Asp3,(E)-Dhb7]MC-RR",,,Microcystin,C48H73N13O12,1024.17,1023.550165,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C\C)/NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H73N13O12/c1-7-31-42(66)55-29(5)41(65)59-34(16-12-22-54-48(51)52)44(68)61-36(46(71)72)25-39(63)57-33(15-11-21-53-47(49)50)43(67)58-32(28(4)40(64)60-35(45(69)70)19-20-38(62)56-31)18-17-26(2)23-27(3)37(73-6)24-30-13-9-8-10-14-30/h7-10,13-14,17-18,23,27-29,32-37H,11-12,15-16,19-22,24-25H2,1-6H3,(H,55,66)(H,56,62)(H,57,63)(H,58,67)(H,59,65)(H,60,64)(H,61,68)(H,69,70)(H,71,72)(H4,49,50,53)(H4,51,52,54)/b18-17+,26-23+,31-7+/t27-,28-,29+,32-,33-,34-,35+,36+,37-/m0/s1",JIVQGWHGELHXHV-UTGMKIGISA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",117064449,,10.1016/S0040-4020(97)10291-5,https://linkinghub.elsevier.com/retrieve/pii/S0040402097102915,"Two new (E)-2-amino-2-butenoic acid (Dhb)-containing microcystins isolated from Oscillatoria agardhii;Tetrahedron;54;43924;;1998;journalArticle;10.1016/S0040-4020(97)10291-5;Sano, Tomoharu; Kaya, Kunimitsu",Oscillatoria/Planktothrix,sp.; agardhii,[Oscillatoria agardhii]NIES 610,,Stereochemistry assumed based on other MC congeners; amino acid analysis
CyanoMetDB_1963,"[D-Ser1,ADMAdda5]MC-LR",,,Microcystin,C50H74N10O14,1039.18,1038.538597,O=C(N(C)C(C(N[C@@H](C1=O)CO)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C50H74N10O14/c1-26(2)22-37-46(68)59-41(49(72)73)30(6)43(65)55-35(16-13-21-53-50(51)52)45(67)54-34(18-17-27(3)23-28(4)39(74-32(8)62)24-33-14-11-10-12-15-33)29(5)42(64)56-36(48(70)71)19-20-40(63)60(9)31(7)44(66)58-38(25-61)47(69)57-37/h10-12,14-15,17-18,23,26,28-30,34-39,41,61H,7,13,16,19-22,24-25H2,1-6,8-9H3,(H,54,67)(H,55,65)(H,56,64)(H,57,69)(H,58,66)(H,59,68)(H,70,71)(H,72,73)(H4,51,52,53)/b18-17+,27-23+/t28-,29-,30-,34-,35-,36+,37-,38+,39-,41+/m0/s1",LIAFLGINUNSQGF-ABEBPWJESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-5-(hydroxymethyl)-8-isobutyl-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101641980,,10.1021/tx00028a003,https://pubs.acs.org/doi/abs/10.1021/tx00028a003,"Three new microcystins, cyclic heptapeptide hepatotoxins, from Nostoc sp. strain 152;Chemical Research in Toxicology;5;4;;1992;journalArticle;10.1021/tx00028a003;Sivonen, Kaarina; Namikoshi, Michio; Evans, William R.; Fardig, Michael; Carmichael, Wayne W.; Rinehart, Kenneth L.",Nostoc,sp.,[Nostoc sp.]152,,Chirality of amino acids confirmed by GC-MS analysis of acid hydrolysate. NMR data not acquired in cited reference.
CyanoMetDB_1964,"[D-Met1,D-Asp3]MC-LR",,,Microcystin,C50H76N10O12S,1041.26,1040.536489,O=C(N(C)C(C(N[C@@H](C1=O)CCSC)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C50H76N10O12S/c1-28(2)24-38-47(67)59-39(49(70)71)27-41(61)54-35(16-13-22-53-50(51)52)45(65)55-34(18-17-29(3)25-30(4)40(72-8)26-33-14-11-10-12-15-33)31(5)43(63)57-37(48(68)69)19-20-42(62)60(7)32(6)44(64)56-36(21-23-73-9)46(66)58-38/h10-12,14-15,17-18,25,28,30-31,34-40H,6,13,16,19-24,26-27H2,1-5,7-9H3,(H,54,61)(H,55,65)(H,56,64)(H,57,63)(H,58,66)(H,59,67)(H,68,69)(H,70,71)(H4,51,52,53)/b18-17+,29-25+/t30-,31-,34-,35-,36+,37+,38-,39+,40-/m0/s1",AKMHMZBZMVAHQA-OWQGMYRZSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-5-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684765,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Microcystis,aeruginosa,[Microcystis aeruginosa]NPLJ-4,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1965,"[ADMAdda5,Mser7]MC-LR ",,,Microcystin,C50H76N10O14,1041.2,1040.554247,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C50H76N10O14/c1-26(2)22-37-46(68)59-41(49(72)73)30(6)43(65)56-35(16-13-21-53-50(51)52)45(67)55-34(18-17-27(3)23-28(4)39(74-32(8)62)24-33-14-11-10-12-15-33)29(5)42(64)57-36(48(70)71)19-20-40(63)60(9)38(25-61)47(69)54-31(7)44(66)58-37/h10-12,14-15,17-18,23,26,28-31,34-39,41,61H,13,16,19-22,24-25H2,1-9H3,(H,54,69)(H,55,67)(H,56,65)(H,57,64)(H,58,66)(H,59,68)(H,70,71)(H,72,73)(H4,51,52,53)/b18-17+,27-23+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,39-,41+/m0/s1",FGMNKDLRQCTWIB-BYOYILFWSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-isobutyl-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6450141,,10.1021/tx00028a003,https://pubs.acs.org/doi/abs/10.1021/tx00028a003,"Three new microcystins, cyclic heptapeptide hepatotoxins, from Nostoc sp. strain 152;Chemical Research in Toxicology;5;4;;1992;journalArticle;10.1021/tx00028a003;Sivonen, Kaarina; Namikoshi, Michio; Evans, William R.; Fardig, Michael; Carmichael, Wayne W.; Rinehart, Kenneth L.",Nostoc,sp.,[Nostoc sp.]152,,Chirality of amino acids confirmed by GC-MS analysis of acid hydrolysate. NMR data not acquired in cited reference.
CyanoMetDB_1966,"[D‐Asp³,Mser7]MC‐RR",,,Microcystin,C48H75N13O13,1042.19,1041.56073,O=C(N(C)[C@@H](CO)C(N[C@H](C)C1=O)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C48H75N13O13/c1-26(22-27(2)37(74-6)23-30-12-8-7-9-13-30)16-17-31-28(3)40(65)59-34(45(70)71)18-19-39(64)61(5)36(25-62)44(69)55-29(4)41(66)58-33(15-11-21-54-48(51)52)43(68)60-35(46(72)73)24-38(63)56-32(42(67)57-31)14-10-20-53-47(49)50/h7-9,12-13,16-17,22,27-29,31-37,62H,10-11,14-15,18-21,23-25H2,1-6H3,(H,55,69)(H,56,63)(H,57,67)(H,58,66)(H,59,65)(H,60,68)(H,70,71)(H,72,73)(H4,49,50,53)(H4,51,52,54)/b17-16+,26-22+/t27-,28-,29+,31-,32-,33-,34+,35+,36-,37-/m0/s1",JSNLJCSMZZDASS-UPNJEQNISA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684696,,N/A,aem.asm.org/content/59/7/2204.short,"Isolation and identification of eight microcystins from thirteen Oscillatoria agardhii strains and structure of a new microcystin; Applied and Environmental Microbiology;59;7;1993;journalArticle;n.a.;R Luukkainen, K Sivonen, M Namikoshi, M Färdig, K L Rinehart, S I Niemelä",Oscillatoria/Planktothrix,agardhii,"49, 195, 214",,Stereochemistry of amino acids determinered by chiral GC; Amino acids and MS analyses used. No 1D or 2D-NMR. Compounds isolated from O. agardhii from Finnish lakes. Subsequently reported in a number of other studies. Location of methyl group on serine moiety (position 7) assumed based on knowledge of other MCs.
CyanoMetDB_1967,[Ser7]MC-RR,,,Microcystin,C48H75N13O13,1042.19,1041.56073,O=C(N[C@@H](CO)C(N[C@H](C)C1=O)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C48H75N13O13/c1-25(22-26(2)36(74-6)23-30-12-8-7-9-13-30)16-17-31-27(3)39(64)60-34(45(70)71)18-19-37(63)56-35(24-62)44(69)55-29(5)41(66)59-33(15-11-21-54-48(51)52)43(68)61-38(46(72)73)28(4)40(65)58-32(42(67)57-31)14-10-20-53-47(49)50/h7-9,12-13,16-17,22,26-29,31-36,38,62H,10-11,14-15,18-21,23-24H2,1-6H3,(H,55,69)(H,56,63)(H,57,67)(H,58,65)(H,59,66)(H,60,64)(H,61,68)(H,70,71)(H,72,73)(H4,49,50,53)(H4,51,52,54)/b17-16+,25-22+/t26-,27-,28-,29+,31-,32-,33-,34+,35-,36-,38+/m0/s1",OYVAKSWRYSRRKU-LLELUXQJSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101642888,,10.1016/0041-0101(92)90521-6,https://linkinghub.elsevier.com/retrieve/pii/0041010192905216,"Two new l-serine variants of microcystins-LR and -RR from Anabaena sp. strains 202 A1 and 202 A2;Toxicon;30;11;;1992;journalArticle;10.1016/0041-0101(92)90521-6;Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Carmichael, Wayne W.; Sun, Furong; Rouhiainen, Leo; Luukkainen, Raija; Rinehart, Kenneth L.",Anabaena,n.a.,"[Anabaena sp.]202 A1, [Anabaena sp.]202 A2",,Stereochemistry defined through amino acid analysis
CyanoMetDB_1968,[seco7][D-Asp3]MC-RR,[seco-1/7][D-Asp3]MC-RR,,Microcystin,C48H75N13O13,1042.19,1041.56073,CC(=O)C(=O)N[C@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@H](CC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](/C=C/C(/C)=C/[C@H](C)[C@@H](OC)Cc1ccccc1)[C@H](C)C(=O)N[C@H](CCC(=O)NC)C(=O)O)C(=O)O,"InChI=1S/C48H75N13O13/c1-26(23-27(2)37(74-7)24-31-13-9-8-10-14-31)17-18-32(28(3)40(65)60-35(45(70)71)19-20-38(63)53-6)58-43(68)33(15-11-21-54-47(49)50)57-39(64)25-36(46(72)73)61-44(69)34(16-12-22-55-48(51)52)59-41(66)29(4)56-42(67)30(5)62/h8-10,13-14,17-18,23,27-29,32-37H,11-12,15-16,19-22,24-25H2,1-7H3,(H,53,63)(H,56,67)(H,57,64)(H,58,68)(H,59,66)(H,60,65)(H,61,69)(H,70,71)(H,72,73)(H4,49,50,54)(H4,51,52,55)/b18-17+,26-23+/t27-,28-,29+,32-,33-,34-,35+,36+,37-/m0/s1",RDMMSXPNHDOGME-LTPNNWFFSA-N,"N2-((2S,3S,4E,6E,8S,9S)-3-((S)-2-((R)-3-carboxy-3-((S)-5-guanidino-2-((R)-2-(2-oxopropanamido)propanamido)pentanamido)propanamido)-5-guanidinopentanamido)-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoyl)-N5-methyl-D-glutamine",11815573,,10.1021/np034036r,https://pubs.acs.org/doi/10.1021/np034036r,"Seco[d-Asp3]microcystin-RR and [d-Asp3,d-Glu(OMe)6]microcystin-RR, Two New Microcystins from a Toxic Water Bloom of the Cyanobacterium Planktothrix rubescens;Journal of Natural Products;67;3;;2004;journalArticle;10.1021/np034036r;Grach-Pogrebinsky, Olga; Sedmak, Bojan; Carmeli, Shmuel",Oscillatoria/Planktothrix,rubescens,n.a.,,"Isolated from a Planktothrix rubescens toxic bloom collected in Lake Bled, Slovenia"
CyanoMetDB_1969,"[D-Asp3,Thr7]MC‐RR",,,Microcystin,C48H75N13O13,1042.19,1041.56073,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(C)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C48H75N13O13/c1-25(22-26(2)36(74-6)23-30-12-8-7-9-13-30)16-17-31-27(3)40(65)59-34(45(70)71)18-19-37(63)61-39(29(5)62)44(69)55-28(4)41(66)58-33(15-11-21-54-48(51)52)43(68)60-35(46(72)73)24-38(64)56-32(42(67)57-31)14-10-20-53-47(49)50/h7-9,12-13,16-17,22,26-29,31-36,39,62H,10-11,14-15,18-21,23-24H2,1-6H3,(H,55,69)(H,56,64)(H,57,67)(H,58,66)(H,59,65)(H,60,68)(H,61,63)(H,70,71)(H,72,73)(H4,49,50,53)(H4,51,52,54)/b17-16+,25-22+/t26-,27-,28+,29?,31-,32-,33-,34+,35+,36-,39?/m0/s1",IVVHVGUGWVJZKJ-VBYGUZBDSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-3,5-dimethylhepta-1,3-dien-1-yl)-8,15-bis(3-guanidinopropyl)-2-(1-hydroxyethyl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684712,,10.1002/jms.1237,http://doi.wiley.com/10.1002/jms.1237,"Consistency between chemotyping of single filaments of Planktothrix rubescens (cyanobacteria) by MALDI-TOF and the peptide patterns of strains determined by HPLC-MS;Journal of Mass Spectrometry;42;8;;2007;journalArticle;10.1002/jms.1237;Welker, Martin; Erhard, Marcel",Planktothrix,rubescens,"173, 208",,"The cited reference did not show a spectrum for this compound. Current assumption is Thr at position-7 but allo-Thr cannot be excluded. Stereochemistry of all building blocks are assumed based on other MC congeners, with Thr remaining undefined."
CyanoMetDB_1970,MC‐HphHty,,,Microcystin,C57H73N7O13,1064.23,1063.526636,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCc2ccc(O)cc2)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCc2ccccc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C57H73N7O13/c1-33(31-34(2)47(77-8)32-41-17-13-10-14-18-41)19-26-43-35(3)50(67)62-46(56(73)74)29-30-48(66)64(7)38(6)53(70)58-37(5)52(69)61-45(27-22-39-15-11-9-12-16-39)55(72)63-49(57(75)76)36(4)51(68)60-44(54(71)59-43)28-23-40-20-24-42(65)25-21-40/h9-21,24-26,31,34-37,43-47,49,65H,6,22-23,27-30,32H2,1-5,7-8H3,(H,58,70)(H,59,71)(H,60,68)(H,61,69)(H,62,67)(H,63,72)(H,73,74)(H,75,76)/b26-19+,33-31+/t34-,35-,36-,37+,43-,44-,45-,46+,47-,49+/m0/s1",GPSIPJQQMCPLFC-ZOGHLDEHSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684766,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Phormidium,n.a.,DVL1003c; LP904C,,"[Shishido 2013] Identification primarily by LC-MS/MS and HRMS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1971,[D-MeO-Glu6]MC-FR,[D-Glu(OMe)6]MC-FR,,Microcystin,C53H74N10O12,1043.21,1042.5488,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C53H74N10O12/c1-30(27-31(2)42(74-8)29-37-19-14-11-15-20-37)22-23-38-32(3)45(65)60-40(52(73)75-9)24-25-43(64)63(7)35(6)48(68)57-34(5)47(67)61-41(28-36-17-12-10-13-18-36)50(70)62-44(51(71)72)33(4)46(66)59-39(49(69)58-38)21-16-26-56-53(54)55/h10-15,17-20,22-23,27,31-34,38-42,44H,6,16,21,24-26,28-29H2,1-5,7-9H3,(H,57,68)(H,58,69)(H,59,66)(H,60,65)(H,61,67)(H,62,70)(H,71,72)(H4,54,55,56)/b23-22+,30-27+/t31-,32-,33-,34+,38-,39-,40+,41-,42-,44+/m0/s1",TUXKJPGQNPVSCV-LBEBTBASSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",146683862,,10.1016/j.envpol.2016.06.055,https://linkinghub.elsevier.com/retrieve/pii/S0269749116305437,"High diversity of microcystins in a Microcystis bloom from an Algerian lake;Environmental Pollution;216;;;2016;journalArticle;10.1016/j.envpol.2016.06.055;Bouhaddada, Ratiba; Nélieu, Sylvie; Nasri, Hichem; Delarue, Ghislaine; Bouaïcha, Noureddine",n.a.,sp.,n.a.,"field sample Lake des Oiseaux (36°42′N 008°07′E), north-eastern Algeria",Bloom samples from Lake des Oiseaux located in north-eastern Algeria. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1972,[D-Leu1]MC-LY,,,Microcystin,C55H77N7O13,1044.24,1043.5579,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C55H77N7O13/c1-30(2)25-42-51(68)60-43(26-31(3)4)53(70)61-47(55(73)74)35(8)49(66)58-44(28-38-18-20-39(63)21-19-38)52(69)56-40(22-17-32(5)27-33(6)45(75-11)29-37-15-13-12-14-16-37)34(7)48(65)57-41(54(71)72)23-24-46(64)62(10)36(9)50(67)59-42/h12-22,27,30-31,33-35,40-45,47,63H,9,23-26,28-29H2,1-8,10-11H3,(H,56,69)(H,57,65)(H,58,66)(H,59,67)(H,60,68)(H,61,70)(H,71,72)(H,73,74)/b22-17+,32-27+/t33-,34-,35-,40-,41+,42+,43-,44-,45-,47+/m0/s1",ANDKUSLFYHFLNO-WVYYMHGOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(4-hydroxybenzyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",139594199,,10.1007/s00216-017-0437-0,http://link.springer.com/10.1007/s00216-017-0437-0,"A high throughput targeted and non-targeted method for the analysis of microcystins and anatoxin-A using on-line solid phase extraction coupled to liquid chromatography–quadrupole time-of-flight high resolution mass spectrometry;Analytical and Bioanalytical Chemistry;409;21;;2017;journalArticle;10.1007/s00216-017-0437-0;Ortiz, Xavier; Korenkova, Eva; Jobst, Karl J.; MacPherson, Karen A.; Reiner, Eric J.",Microcystis,aeruginosa,CPCC-464,,
CyanoMetDB_1973,MC‐M(O2)R,MC‐M(O2)R (oxidation artefact),,Microcystin,C48H72N10O14S,1045.22,1044.495018,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCS(C)(=O)=O)=O)=O)=O)=O,"InChI=1S/C48H72N10O14S/c1-26(24-27(2)37(72-8)25-32-14-11-10-12-15-32)17-18-33-28(3)40(60)56-36(46(66)67)19-20-38(59)58(7)31(6)43(63)52-30(5)42(62)55-35(21-23-73(9,70)71)45(65)57-39(47(68)69)29(4)41(61)54-34(44(64)53-33)16-13-22-51-48(49)50/h10-12,14-15,17-18,24,27-30,33-37,39H,6,13,16,19-23,25H2,1-5,7-9H3,(H,52,63)(H,53,64)(H,54,61)(H,55,62)(H,56,60)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,26-24+/t27-,28-,29-,30+,33-,34-,35-,36+,37-,39+/m0/s1",NHPKXVVXNWNWBU-MCUDKQGFSA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-(3-sulfinopropyl)-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684785,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,MS2 available in the article
CyanoMetDB_1974,[Dhb7]MC-YR,,,Microcystin,C52H72N10O13,1045.21,1044.528032,O=C(NC(C(N[C@@H](C1=O)C)=O)=CC)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O13/c1-8-36-47(68)56-32(6)46(67)61-40(26-34-17-19-35(63)20-18-34)49(70)62-43(51(73)74)31(5)45(66)59-38(15-12-24-55-52(53)54)48(69)58-37(30(4)44(65)60-39(50(71)72)22-23-42(64)57-36)21-16-28(2)25-29(3)41(75-7)27-33-13-10-9-11-14-33/h8-11,13-14,16-21,25,29-32,37-41,43,63H,12,15,22-24,26-27H2,1-7H3,(H,56,68)(H,57,64)(H,58,69)(H,59,66)(H,60,65)(H,61,67)(H,62,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-16+,28-25+,36-8?/t29-,30-,31-,32+,37-,38-,39+,40-,41-,43+/m0/s1",XJSOCTMEOQATBC-GWDXHOIDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-ethylidene-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802418,,10.3390/toxins11010013,https://www.mdpi.com/2072-6651/11/1/13,"Comparative Analysis of Microcystin Prevalence in Michigan Lakes by Online Concentration LC/MS/MS and ELISA;Toxins;11;1;;2019;journalArticle;10.3390/toxins11010013;Birbeck, Johnna A.; Westrick, Judy A.; O’Neill, Grace M.; Spies, Brian; Szlag, David C.",n.a.,n.a.,n.a.,"field samples, Great Lakes (USA) including Brimley Bay (SUP: Lake Superior), Lake St. Clair Metro Park (STC: Lake St. Clair), and Lake Erie Metro Park (ERI: Northwest Lake Erie).","Insufficient structural infromation in paper to confirm identity. ""the possibility that [Dhb7]-MC-YR may be the constitutional isomer [D-Asp3,Dhb7]MC-HtyR cannot be excluded"""
CyanoMetDB_1975,"[D-Asp3,ADMAdda5]MC-LR",,,Microcystin,C49H72N10O13,1009.16,1008.528033,C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC(=O)C)/C,"InChI=1S/C49H72N10O13/c1-26(2)22-37-46(67)58-38(48(70)71)25-40(61)54-35(16-13-21-52-49(50)51)45(66)55-34(18-17-27(3)23-28(4)39(72-32(8)60)24-33-14-11-10-12-15-33)29(5)42(63)56-36(47(68)69)19-20-41(62)59(9)31(7)44(65)53-30(6)43(64)57-37/h10-12,14-15,17-18,23,26,28-30,34-39H,7,13,16,19-22,24-25H2,1-6,8-9H3,(H,53,65)(H,54,61)(H,55,66)(H,56,63)(H,57,64)(H,58,67)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,27-23+/t28-,29-,30+,34-,35-,36+,37-,38+,39-/m0/s1",PLFFZWBHDRTEHV-VLVYYTPOSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-((diaminomethylene)amino)propyl)-8-isobutyl-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",14752804,,10.1021/jo00312a019,https://pubs.acs.org/doi/abs/10.1021/jo00312a019,"Structures of three new cyclic heptapeptide hepatotoxins produced by the cyanobacterium (blue-green alga) Nostoc sp. strain 152;The Journal of Organic Chemistry;55;25;;1990;journalArticle;10.1021/jo00312a019;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Sivonen, Kaarina; Carmichael, Wayne W.",Nostoc,n.a.,152; IO-102-I,,
CyanoMetDB_1976,[Dha7]MC-HtyR,,,Microcystin,C52H72N10O13,1045.19,1044.528033,O=C(NC(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O13/c1-28(26-29(2)41(75-7)27-35-12-9-8-10-13-35)15-21-37-30(3)44(65)61-40(50(71)72)23-24-42(64)56-32(5)46(67)57-33(6)47(68)60-39(22-18-34-16-19-36(63)20-17-34)49(70)62-43(51(73)74)31(4)45(66)59-38(48(69)58-37)14-11-25-55-52(53)54/h8-10,12-13,15-17,19-21,26,29-31,33,37-41,43,63H,5,11,14,18,22-25,27H2,1-4,6-7H3,(H,56,64)(H,57,67)(H,58,69)(H,59,66)(H,60,68)(H,61,65)(H,62,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-15+,28-26+/t29-,30-,31-,33+,37-,38-,39-,40+,41-,43+/m0/s1",KGAVCHMHGJSYBJ-ZNUBTALFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101642107,,10.1021/tx00029a011,https://pubs.acs.org/doi/abs/10.1021/tx00029a011,"Structures of three new homotyrosine-containing microcystins and a new homophenylalanine variant from Anabaena sp. strain 66;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a011;Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Carmichael, Wayne W.; Rouhiainen, Leo; Luukkainen, Raija; Rinehart, Kenneth L.",Anabaena,n.a.,[Anabaena sp.]66,,Stereochemistry defined by chiral GC-MS analyses.
CyanoMetDB_1977,"[D-Asp3,(E)-Dhb7]MC-HtyR",,,Microcystin,C52H72N10O13,1045.19,1044.528033,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C\C)/NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H72N10O13/c1-7-36-47(68)56-32(5)46(67)60-39(22-18-33-16-19-35(63)20-17-33)49(70)62-41(51(73)74)28-44(65)58-38(14-11-25-55-52(53)54)48(69)59-37(31(4)45(66)61-40(50(71)72)23-24-43(64)57-36)21-15-29(2)26-30(3)42(75-6)27-34-12-9-8-10-13-34/h7-10,12-13,15-17,19-21,26,30-32,37-42,63H,11,14,18,22-25,27-28H2,1-6H3,(H,56,68)(H,57,64)(H,58,65)(H,59,69)(H,60,67)(H,61,66)(H,62,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-15+,29-26+,36-7+/t30-,31-,32+,37-,38-,39-,40+,41+,42-/m0/s1",VRSPDCJDWOZKSK-FDUALHMESA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",15837270,,10.1016/S0040-4020(97)10291-5,https://linkinghub.elsevier.com/retrieve/pii/S0040402097102915,"Two new (E)-2-amino-2-butenoic acid (Dhb)-containing microcystins isolated from Oscillatoria agardhii;Tetrahedron;54;43924;;1998;journalArticle;10.1016/S0040-4020(97)10291-5;Sano, Tomoharu; Kaya, Kunimitsu",Oscillatoria/Planktothrix,agardhii,[Oscillatoria/Planktothrix agardhii]CCAP 1459/14,,Stereochemistry well-defined via chiral amino acid analyses and 2D-NMR.
CyanoMetDB_1978,"[D-Asp3,(Z)-Dhb7]MC-HtyR",,,Microcystin,C52H72N10O13,1045.19,1044.528033,O=C(N/C(C(N[C@H](C)C1=O)=O)=C\C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O13/c1-7-36-47(68)56-32(5)46(67)60-39(22-18-33-16-19-35(63)20-17-33)49(70)62-41(51(73)74)28-44(65)58-38(14-11-25-55-52(53)54)48(69)59-37(31(4)45(66)61-40(50(71)72)23-24-43(64)57-36)21-15-29(2)26-30(3)42(75-6)27-34-12-9-8-10-13-34/h7-10,12-13,15-17,19-21,26,30-32,37-42,63H,11,14,18,22-25,27-28H2,1-6H3,(H,56,68)(H,57,64)(H,58,65)(H,59,69)(H,60,67)(H,61,66)(H,62,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-15+,29-26+,36-7-/t30-,31-,32+,37-,38-,39-,40+,41+,42-/m0/s1",VRSPDCJDWOZKSK-ZWNPEXSNSA-N,"(5R,8S,11R,15S,18S,19S,22R,Z)-2-ethylidene-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",21635773,,10.1021/np980047m,https://pubs.acs.org/doi/10.1021/np980047m,"Two ( Z )-Dehydrobutyrine-Containing Microcystins from a Hepatotoxic Bloom of Oscillatoria a gardhii from Soulseat Loch, Scotland;Journal of Natural Products;61;6;;1998;journalArticle;10.1021/np980047m;Sano, Tomoharu; Beattie, Kenneth A.; Codd, Geoffrey A.; Kaya, Kunimitsu",Oscillatoria/Planktothrix,agardhii,bloom,,"Detected in cyanobacterial cells collected from an extensive shoreline scum at Soulseat Loch, southwest Scotland (O. agardhii)"
CyanoMetDB_1979,[(6Z)-Adda5]MC-LR,,,Microcystin,C49H74N10O12,995.17,994.5487682,C[C@@H](\C=C(\C)/C=C/[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24-/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",ZYZCGGRZINLQBL-SGIIWDTFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3Z,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",6540780,,10.1016/0041-0101(90)90006-S,https://linkinghub.elsevier.com/retrieve/pii/004101019090006S,"Isolation and characterization of the minor components associated with microcystins LR and RR in the cyanobacterium (blue-green algae);Toxicon;28;1;;1990;journalArticle;10.1016/0041-0101(90)90006-S;Harada, Ken-ichi; Matsuura, Kenji; Suzuki, Makoto; Watanabe, Mariyo F.; Oishi, Shinshi; Dahlem, Andrew M.; Beasley, Val R.; Carmichael, Wayne W.",Microcystis,viridis,n.a.,,Detected in field samples collected from lakes Tsukui and Sagami in Kanagawa prefecture in Japan. The samples were identified as containing primarily M. viridis.
CyanoMetDB_1980,[D-Asp3]MC-HtyR,,,Microcystin,C52H72N10O13,1045.19,1044.528033,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O13/c1-29(26-30(2)42(75-7)27-35-12-9-8-10-13-35)15-21-37-31(3)45(66)60-40(50(71)72)23-24-44(65)62(6)33(5)47(68)56-32(4)46(67)59-39(22-18-34-16-19-36(63)20-17-34)49(70)61-41(51(73)74)28-43(64)57-38(48(69)58-37)14-11-25-55-52(53)54/h8-10,12-13,15-17,19-21,26,30-32,37-42,63H,5,11,14,18,22-25,27-28H2,1-4,6-7H3,(H,56,68)(H,57,64)(H,58,69)(H,59,67)(H,60,66)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-15+,29-26+/t30-,31-,32+,37-,38-,39-,40+,41+,42-/m0/s1",BTHUKOWVYGPUOP-QDFQMAEMSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",15160479,,10.1021/tx00023a008,https://pubs.acs.org/doi/abs/10.1021/tx00023a008,"Microcystins from Anabaena flos-aquae NRC 525-17;Chemical Research in Toxicology;4;5;;1991;journalArticle;10.1021/tx00023a008;Harada, Kenichi; Ogawa, Kiyoshi; Kimura, Yukio; Murata, Hideaki; Suzuki, Makoto; Thorn, Patti M.; Evans, William R.; Carmichael, Wayne W.",Anabaena/Dolichospermum,flos aquae,NRC 525-17,,Stereochemisty defined by chiral amino acid analysis
CyanoMetDB_1981,[(6Z)-Adda5]MC-RR,,,Microcystin,C49H75N13O12,1038.2,1037.565815,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C\[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C49H75N13O12/c1-26(24-27(2)37(74-8)25-32-14-10-9-11-15-32)18-19-33-28(3)40(64)60-36(46(70)71)20-21-38(63)62(7)31(6)43(67)56-30(5)42(66)59-35(17-13-23-55-49(52)53)45(69)61-39(47(72)73)29(4)41(65)58-34(44(68)57-33)16-12-22-54-48(50)51/h9-11,14-15,18-19,24,27-30,33-37,39H,6,12-13,16-17,20-23,25H2,1-5,7-8H3,(H,56,67)(H,57,68)(H,58,65)(H,59,66)(H,60,64)(H,61,69)(H,70,71)(H,72,73)(H4,50,51,54)(H4,52,53,55)/b19-18+,26-24-/t27-,28-,29-,30+,33-,34-,35-,36+,37-,39+/m0/s1",JIGDOBKZMULDHS-SRKJTSIASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-18-((1E,3Z,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",71312371,,10.1016/0041-0101(90)90006-S,https://linkinghub.elsevier.com/retrieve/pii/004101019090006S,"Isolation and characterization of the minor components associated with microcystins LR and RR in the cyanobacterium (blue-green algae);Toxicon;28;1;;1990;journalArticle;10.1016/0041-0101(90)90006-S;Harada, Ken-ichi; Matsuura, Kenji; Suzuki, Makoto; Watanabe, Mariyo F.; Oishi, Shinshi; Dahlem, Andrew M.; Beasley, Val R.; Carmichael, Wayne W.",n.a.,n.a.,n.a.,"field sample, Lakes Tsukui and Sagamii in Kanagawa prefecture in Japan, containing Microcystis viridis","Secondary ion mass spectrometry (original Harada paper) + 2D DQF-COSY, HMBC, HMQC and ROESY NMR. In field samples collected from Lakes Tsukui and Sagami in Kanagawa prefecture in Japan. The samples were identified as containing primarily M. viridis"
CyanoMetDB_1982,MC-(H2)YR,,,Microcystin,C52H74N10O13,1047.22,1046.54368,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC[C@@H](O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H74N10O13/c1-28(25-29(2)41(75-8)27-34-13-10-9-11-14-34)16-21-37-30(3)44(65)59-39(50(71)72)22-23-42(64)62(7)33(6)47(68)56-32(5)46(67)60-40(26-35-17-19-36(63)20-18-35)49(70)61-43(51(73)74)31(4)45(66)58-38(48(69)57-37)15-12-24-55-52(53)54/h9-11,13-14,16-19,21,25,29-32,36-41,43,63H,6,12,15,20,22-24,26-27H2,1-5,7-8H3,(H,56,68)(H,57,69)(H,58,66)(H,59,65)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-16+,28-25+/t29-,30-,31-,32+,36-,37-,38-,39+,40-,41-,43+/m0/s1",BYGCVEXGEJFNCQ-JPSVLHQASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(((R)-4-hydroxycyclohexa-1,5-dien-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683858,,10.1016/j.toxicon.2019.06.006,https://linkinghub.elsevier.com/retrieve/pii/S0041010119301795,"Comprehensive multi-technique approach reveals the high diversity of microcystins in field collections and an associated isolate of Microcystis aeruginosa from a Turkish lake;Toxicon;167;;;2019;journalArticle;10.1016/j.toxicon.2019.06.006;Yilmaz, Mete; Foss, Amanda J.; Miles, Christopher O.; Özen, Mihriban; Demir, Nilsun; Balcı, Muharrem; Beach, Daniel G.",Microcystis,aeruginosa,AQUAMEB-24,,Location of hydrogenation in Tyr ring is speculative and stereochemistry assumed from another bacterial H2T product (Walsh et al.)
CyanoMetDB_1983,MC‐HphHph,,,Microcystin,C57H73N7O12,1048.23,1047.531721,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCC3=CC=CC=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC4=CC=CC=C4)=O)=O)=O)=O,"InChI=1S/C57H73N7O12/c1-34(32-35(2)47(76-8)33-42-22-16-11-17-23-42)24-27-43-36(3)50(66)62-46(56(72)73)30-31-48(65)64(7)39(6)53(69)58-38(5)52(68)61-45(29-26-41-20-14-10-15-21-41)55(71)63-49(57(74)75)37(4)51(67)60-44(54(70)59-43)28-25-40-18-12-9-13-19-40/h9-24,27,32,35-38,43-47,49H,6,25-26,28-31,33H2,1-5,7-8H3,(H,58,69)(H,59,70)(H,60,67)(H,61,68)(H,62,66)(H,63,71)(H,72,73)(H,74,75)/b27-24+,34-32+/t35-,36-,37-,38+,43-,44-,45-,46+,47-,49+/m0/s1",VJPJHXOXFRNWQY-VKXHRRFASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8,15-diphenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684767,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Phormidium,n.a.,DVL1003c; LP904C,,"Identification primarily by LC-MS/MS and HRMS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1984,"[D‐Asp3,Ser7]MC‐HtyR",,,Microcystin,C51H72N10O14,1049.18,1048.522947,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)[C@H](CO)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H72N10O14/c1-28(24-29(2)41(75-5)25-33-10-7-6-8-11-33)13-19-35-30(3)44(66)60-38(49(71)72)21-22-42(64)57-40(27-62)48(70)55-31(4)45(67)59-37(20-16-32-14-17-34(63)18-15-32)47(69)61-39(50(73)74)26-43(65)56-36(46(68)58-35)12-9-23-54-51(52)53/h6-8,10-11,13-15,17-19,24,29-31,35-41,62-63H,9,12,16,20-23,25-27H2,1-5H3,(H,55,70)(H,56,65)(H,57,64)(H,58,68)(H,59,67)(H,60,66)(H,61,69)(H,71,72)(H,73,74)(H4,52,53,54)/b19-13+,28-24+/t29-,30-,31+,35-,36-,37-,38+,39+,40-,41-/m0/s1",OAOGBTSKBZVXOB-FQYRTJBPSA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684731,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Anabaena,n.a.,[Anabaena sp.]66A,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1985,"[D-Asp³,Mser7]MC‐RY",,,Microcystin,C51H72N10O14,1049.18,1048.522947,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C51H72N10O14/c1-28(23-29(2)41(75-6)25-32-11-8-7-9-12-32)14-19-35-30(3)44(66)59-37(49(71)72)20-21-43(65)61(5)40(27-62)48(70)55-31(4)45(67)58-36(13-10-22-54-51(52)53)46(68)60-39(50(73)74)26-42(64)56-38(47(69)57-35)24-33-15-17-34(63)18-16-33/h7-9,11-12,14-19,23,29-31,35-41,62-63H,10,13,20-22,24-27H2,1-6H3,(H,55,70)(H,56,64)(H,57,69)(H,58,67)(H,59,66)(H,60,68)(H,71,72)(H,73,74)(H4,52,53,54)/b19-14+,28-23+/t29-,30-,31+,35-,36-,37+,38-,39+,40-,41-/m0/s1",JXIGYFDYIBIRMX-VODXBEFOSA-N,"8-(3-((diaminomethylene)amino)propyl)-15-(4-hydroxybenzyl)-2-(hydroxymethyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802145,,10.1021/es301808h,https://pubs.acs.org/doi/10.1021/es301808h,"Thiol Derivatization for LC-MS Identification of Microcystins in Complex Matrices;Environmental Science & Technology;46;16;;2012;journalArticle;10.1021/es301808h;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,aeruginosa,CYA548,,"Stereochemistry assumed based on other MC congeners (LC-MS/MS and HRMS analyses unable to confirm this). MC-RY was extensively analysed by 1D and 2D-NMR, hence higher confidence in assigned stereochemistry of this compound."
CyanoMetDB_1986,[Ser7]MC-YR,,,Microcystin,C51H72N10O14,1049.18,1048.522947,O=C(N[C@@H](CO)C(N[C@@H](C1=O)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C51H72N10O14/c1-27(23-28(2)40(75-6)25-32-11-8-7-9-12-32)14-19-35-29(3)43(65)59-37(49(71)72)20-21-41(64)56-39(26-62)48(70)55-31(5)45(67)60-38(24-33-15-17-34(63)18-16-33)47(69)61-42(50(73)74)30(4)44(66)58-36(46(68)57-35)13-10-22-54-51(52)53/h7-9,11-12,14-19,23,28-31,35-40,42,62-63H,10,13,20-22,24-26H2,1-6H3,(H,55,70)(H,56,64)(H,57,68)(H,58,66)(H,59,65)(H,60,67)(H,61,69)(H,71,72)(H,73,74)(H4,52,53,54)/b19-14+,27-23+/t28-,29-,30-,31+,35-,36-,37+,38-,39-,40-,42+/m0/s1",LDSNYTLQVHZIJF-SGAHCBCOSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683841,,10.1038/ja.2006.95,http://www.nature.com/articles/ja200695,"Structural Characterization of Microcystins by LC/MS/MS under Ion Trap Conditions;The Journal of Antibiotics;59;11;;2006;journalArticle;10.1038/ja.2006.95;Mayumi, Tsuyoshi; Kato, Hajime; Imanishi, Susumu; Kawasaki, Yoshito; Hasegawa, Masateru; Harada, Ken-ichi",n.a.,n.a.,n.a.,"field sample, two Microcystis cell materials: one from a surface bloom in a farm pond in Monroe, Wisconsin U.S.A., one from a culture strain (M-228) collected in Lake Suwa in Japan ",Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1987,MC-RA,,,Microcystin,C46H68N10O12,953.09,952.5018179,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C46H68N10O12/c1-24(22-25(2)35(68-9)23-31-14-11-10-12-15-31)17-18-32-26(3)38(58)54-34(44(64)65)19-20-36(57)56(8)30(7)42(62)51-29(6)41(61)53-33(16-13-21-49-46(47)48)43(63)55-37(45(66)67)27(4)39(59)50-28(5)40(60)52-32/h10-12,14-15,17-18,22,25-29,32-35,37H,7,13,16,19-21,23H2,1-6,8-9H3,(H,50,59)(H,51,62)(H,52,60)(H,53,61)(H,54,58)(H,55,63)(H,64,65)(H,66,67)(H4,47,48,49)/b18-17+,24-22+/t25-,26-,27-,28-,29+,32-,33-,34+,35-,37+/m0/s1",RVBWUYJOJNTTSZ-CGZJSGPVSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,15,19-pentamethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid",56928147,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",Microcystis,sp.,n.a.,,
CyanoMetDB_1988,[ADMAdda5]MC‐HilHar,,,Microcystin,C52H78N10O13,1051.23,1050.574983,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C[C@@H](C)CC)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C52H78N10O13/c1-11-28(2)26-40-49(70)61-43(51(73)74)32(6)45(66)58-38(19-15-16-24-55-52(53)54)48(69)57-37(21-20-29(3)25-30(4)41(75-35(9)63)27-36-17-13-12-14-18-36)31(5)44(65)59-39(50(71)72)22-23-42(64)62(10)34(8)47(68)56-33(7)46(67)60-40/h12-14,17-18,20-21,25,28,30-33,37-41,43H,8,11,15-16,19,22-24,26-27H2,1-7,9-10H3,(H,56,68)(H,57,69)(H,58,66)(H,59,65)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b21-20+,29-25+/t28-,30-,31-,32-,33+,37-,38-,39+,40-,41-,43+/m0/s1",MDHSZZGVMIHVMT-FEKRJCKDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-1,5,12,19-tetramethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684732,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]152,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_1989,"[D-Leu1,D-Asp³,ADMAdda5]MC‐LR",,,Microcystin,C52H78N10O13,1051.23,1050.574983,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C52H78N10O13/c1-28(2)23-39-48(69)60-40(24-29(3)4)49(70)61-41(51(73)74)27-43(64)56-37(17-14-22-55-52(53)54)47(68)57-36(19-18-30(5)25-31(6)42(75-34(9)63)26-35-15-12-11-13-16-35)32(7)45(66)58-38(50(71)72)20-21-44(65)62(10)33(8)46(67)59-39/h11-13,15-16,18-19,25,28-29,31-32,36-42H,8,14,17,20-24,26-27H2,1-7,9-10H3,(H,56,64)(H,57,68)(H,58,66)(H,59,67)(H,60,69)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b19-18+,30-25+/t31-,32-,36-,37-,38+,39+,40-,41+,42-/m0/s1",UJEVEFCMHNHXFQ-LIKYXQTASA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-5,8-diisobutyl-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802359,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,"Stereochemistry assumed based on other MC congeners. Bioaccumulated in lichen. Detected in Nephroma cellulosum and Peltigera evansiana (lichen species). Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_1990,"[D-Leu1,Adda(O)5]MC-LR","[D-Leu1,ketoAdda5]MC-LR",,Microcystin,C52H78N10O13,1051.23,1050.575,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C=O)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C52H78N10O13/c1-28(2)23-39-48(69)60-40(24-29(3)4)49(70)61-43(51(73)74)32(7)45(66)57-37(17-14-22-55-52(53)54)47(68)56-36(19-18-35(27-63)25-30(5)41(75-10)26-34-15-12-11-13-16-34)31(6)44(65)58-38(50(71)72)20-21-42(64)62(9)33(8)46(67)59-39/h11-13,15-16,18-19,25,27-32,36-41,43H,8,14,17,20-24,26H2,1-7,9-10H3,(H,56,68)(H,57,66)(H,58,65)(H,59,67)(H,60,69)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b19-18+,35-25-/t30-,31-,32-,36-,37-,38+,39+,40-,41-,43+/m0/s1",UHRXXXBMTGUEJZ-DWMFVRHXSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3Z,5S,6S)-3-formyl-6-methoxy-5-methyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-5,8-diisobutyl-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802356,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Location of carbonyl in Adda chain not fully defined: Plausible structure. The accurate m/z indicates oxidation at a CH rather than across a double bond. Compounds CyanoMetDB_1990 and CyanoMetDB_2001 were found together in the same sample, and so are probably related to each other. MS/MS indicates oxidation to have taken place between C-2 and C-8. The most favourable position for oxidation would be an allylic CH. Since the other allylic positions (C-3 and C-8 are tri-substituted and therefore cannot be oxidised to carbonyl groups) one educated guess would be that these compounds are most likely to have been oxidised on the 6-methyl group. The aldehyde derivative would have additional stabilisation through conjugation. It ought also to react with thiols, but that reaction would likely be slow due to steric hindrance."
CyanoMetDB_1991,[D-Leu1]MC‐HilR,,,Microcystin,C53H82N10O12,1051.28,1050.611368,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)C[C@@H](C)CC)=O)=O)=O)=O,"InChI=1S/C53H82N10O12/c1-12-30(4)27-41-50(70)62-44(52(73)74)34(8)46(66)58-38(19-16-24-56-53(54)55)48(68)57-37(21-20-31(5)26-32(6)42(75-11)28-36-17-14-13-15-18-36)33(7)45(65)59-39(51(71)72)22-23-43(64)63(10)35(9)47(67)60-40(25-29(2)3)49(69)61-41/h13-15,17-18,20-21,26,29-30,32-34,37-42,44H,9,12,16,19,22-25,27-28H2,1-8,10-11H3,(H,57,68)(H,58,66)(H,59,65)(H,60,67)(H,61,69)(H,62,70)(H,71,72)(H,73,74)(H4,54,55,56)/b21-20+,31-26+/t30-,32-,33-,34-,37-,38-,39+,40+,41-,42-,44+/m0/s1",YDQPVIVPYIKYPZ-FRZRWRADSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684768,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Microcystis,sp.,[Microcystis sp.]RST9501,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_1992,[D-Leu1]MC‐LHar,,,Microcystin,C53H82N10O12,1051.28,1050.611368,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C53H82N10O12/c1-29(2)25-40-49(69)61-41(26-30(3)4)50(70)62-44(52(73)74)34(8)46(66)58-38(19-15-16-24-56-53(54)55)48(68)57-37(21-20-31(5)27-32(6)42(75-11)28-36-17-13-12-14-18-36)33(7)45(65)59-39(51(71)72)22-23-43(64)63(10)35(9)47(67)60-40/h12-14,17-18,20-21,27,29-30,32-34,37-42,44H,9,15-16,19,22-26,28H2,1-8,10-11H3,(H,57,68)(H,58,66)(H,59,65)(H,60,67)(H,61,69)(H,62,70)(H,71,72)(H,73,74)(H4,54,55,56)/b21-20+,31-27+/t32-,33-,34-,37-,38-,39+,40+,41-,42-,44+/m0/s1",WZZBZIMDYIUNIJ-SGPOGQQTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(4-guanidinobutyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802407,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,Stereochemistry inferred from other MC congeners. Bioaccumulated in lichen. Identified in Peltigera evansiana (liquen species)
CyanoMetDB_1993,"[D-Leu1,D-MeO-Glu6]MC-LR","[D-Leu1,D-Glu(OMe)6]MC-LR",,Microcystin,C53H82N10O12,1051.28,1050.611368,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C53H82N10O12/c1-29(2)25-40-49(69)61-41(26-30(3)4)50(70)62-44(51(71)72)34(8)46(66)58-38(19-16-24-56-53(54)55)48(68)57-37(21-20-31(5)27-32(6)42(74-11)28-36-17-14-13-15-18-36)33(7)45(65)59-39(52(73)75-12)22-23-43(64)63(10)35(9)47(67)60-40/h13-15,17-18,20-21,27,29-30,32-34,37-42,44H,9,16,19,22-26,28H2,1-8,10-12H3,(H,57,68)(H,58,66)(H,59,65)(H,60,67)(H,61,69)(H,62,70)(H,71,72)(H4,54,55,56)/b21-20+,31-27+/t32-,33-,34-,37-,38-,39+,40+,41-,42-,44+/m0/s1",FDKBJUJOGLCGGN-SGPOGQQTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",146683870,,10.1002/rcm.7098,http://doi.wiley.com/10.1002/rcm.7098,"Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - unambiguous assignment of product ions by tandem mass spectrometry: Discovery of microcystins by MS/MS;Rapid Communications in Mass Spectrometry;29;2;;2015;journalArticle;10.1002/rcm.7098;Qi, Yulin; Rosso, Lorena; Sedan, Daniela; Giannuzzi, Leda; Andrinolo, Dario; Volmer, Dietrich A.",Microcystis,aeruginosa,[Microcystis aeruginosa] CAAT 2005-3,,Stereochemistry assumed based on other MC congeners (identification by MS only). Also detected in Peltigera degenii (lichen species)
CyanoMetDB_1994,[D-Hil1]MC-LR,,,Microcystin,C53H82N10O12,1051.28,1050.61137,O=C(N(C)C(C(N[C@@H](C1=O)C[C@@H](C)CC)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C53H82N10O12/c1-12-30(4)27-41-49(69)61-40(25-29(2)3)50(70)62-44(52(73)74)34(8)46(66)58-38(19-16-24-56-53(54)55)48(68)57-37(21-20-31(5)26-32(6)42(75-11)28-36-17-14-13-15-18-36)33(7)45(65)59-39(51(71)72)22-23-43(64)63(10)35(9)47(67)60-41/h13-15,17-18,20-21,26,29-30,32-34,37-42,44H,9,12,16,19,22-25,27-28H2,1-8,10-11H3,(H,57,68)(H,58,66)(H,59,65)(H,60,67)(H,61,69)(H,62,70)(H,71,72)(H,73,74)(H4,54,55,56)/b21-20+,31-26+/t30-,32-,33-,34-,37-,38-,39+,40-,41+,42-,44+/m0/s1",HVANFGKLTKFVDQ-GBHADRNMSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-5-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802100,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ",Stereochemistry/connectivity in Hil side-chain not confirmed
CyanoMetDB_1995,"[D‐Asp3,(E)-Dhb7]MC‐HtyY",,,Microcystin,C55H69N7O14,1052.17,1051.49025,O=C(N/C(C(N[C@@H](C1=O)C)=O)=C/C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC4=CC=C(O)C=C4)=O)=O)=O)=O,"InChI=1S/C55H69N7O14/c1-7-40-51(69)56-34(5)50(68)60-42(24-18-35-14-19-38(63)20-15-35)52(70)62-45(55(74)75)30-48(66)58-44(28-37-16-21-39(64)22-17-37)53(71)59-41(33(4)49(67)61-43(54(72)73)25-26-47(65)57-40)23-13-31(2)27-32(3)46(76-6)29-36-11-9-8-10-12-36/h7-17,19-23,27,32-34,41-46,63-64H,18,24-26,28-30H2,1-6H3,(H,56,69)(H,57,65)(H,58,66)(H,59,71)(H,60,68)(H,61,67)(H,62,70)(H,72,73)(H,74,75)/b23-13+,31-27+,40-7+/t32-,33-,34+,41-,42-,43+,44-,45+,46-/m0/s1",WIUASVUEJTVYML-YBHJWNOCSA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-15-(4-hydroxybenzyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802394,,10.1021/np800397u,https://pubs.acs.org/doi/10.1021/np800397u,"Isolation and Structure Determination of Two Microcystins and Sequence Comparison of the McyABC Adenylation Domains in Planktothrix Species;Journal of Natural Products;71;11;;2008;journalArticle;10.1021/np800397u;Christiansen, Guntram; Yoshida, Wesley Y.; Blom, Judith F.; Portmann, Cyril; Gademann, Karl; Hemscheidt, Thomas; Kurmayer, Rainer",Planktothrix,rubescens,[Planktothrix rubescens]80,,Thoroughly characterised by complementary techniques.
CyanoMetDB_1996,MC‐YY,,,Microcystin,C55H69N7O14,1052.17,1051.49025,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC4=CC=C(C=C4)O)=O)=O)=O)=O,"InChI=1S/C55H69N7O14/c1-30(26-31(2)45(76-8)29-36-12-10-9-11-13-36)14-23-41-32(3)48(66)58-42(54(72)73)24-25-46(65)62(7)35(6)51(69)56-34(5)50(68)60-44(28-38-17-21-40(64)22-18-38)53(71)61-47(55(74)75)33(4)49(67)59-43(52(70)57-41)27-37-15-19-39(63)20-16-37/h9-23,26,31-34,41-45,47,63-64H,6,24-25,27-29H2,1-5,7-8H3,(H,56,69)(H,57,70)(H,58,66)(H,59,67)(H,60,68)(H,61,71)(H,72,73)(H,74,75)/b23-14+,30-26+/t31-,32-,33-,34+,41-,42+,43-,44-,45-,47+/m0/s1",PGLPSVMYGXSNBK-KQTAPMBTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684775,,10.1371/journal.pone.0091476,https://dx.plos.org/10.1371/journal.pone.0091476,"Selectivity and Potency of Microcystin Congeners against OATP1B1 and OATP1B3 Expressing Cancer Cells;PLoS ONE;9;3;;2014;journalArticle;10.1371/journal.pone.0091476;Niedermeyer, Timo H. J.; Daily, Abigail; Swiatecka-Hagenbruch, Monika; Moscow, Jeffrey A.",Microcystis,aeruginosa,[Microcystis aeruginosa]CBT 850,,Stereochemistry determined by 2D-NMR.
CyanoMetDB_1997,[D-Leu1]MC-LR,,,Microcystin,C52H80N10O12,1037.25,1036.595718,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C52H80N10O12/c1-28(2)24-39-48(68)60-40(25-29(3)4)49(69)61-43(51(72)73)33(8)45(65)57-37(18-15-23-55-52(53)54)47(67)56-36(20-19-30(5)26-31(6)41(74-11)27-35-16-13-12-14-17-35)32(7)44(64)58-38(50(70)71)21-22-42(63)62(10)34(9)46(66)59-39/h12-14,16-17,19-20,26,28-29,31-33,36-41,43H,9,15,18,21-25,27H2,1-8,10-11H3,(H,56,67)(H,57,65)(H,58,64)(H,59,66)(H,60,68)(H,61,69)(H,70,71)(H,72,73)(H4,53,54,55)/b20-19+,30-26+/t31-,32-,33-,36-,37-,38+,39+,40-,41-,43+/m0/s1",PYRKYAINAPVHFV-OGPAHFFASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",636790,,10.1016/S0031-9422(00)00335-6,https://linkinghub.elsevier.com/retrieve/pii/S0031942200003356,"[d-Leu1]Microcystin-LR, from the cyanobacterium Microcystis RST 9501 and from a Microcystis bloom in the Patos Lagoon estuary, Brazil;Phytochemistry;55;5;;2000;journalArticle;10.1016/S0031-9422(00)00335-6;Matthiensen, Alexandre; Beattie, Kenneth A; Yunes, João S; Kaya, Kunimitsu; Codd, Geoffrey A",Microcystis,sp.,RST 9501,,"Microcystis isolated from Patos Lagoon, Brazil, 1995 and 1996."
CyanoMetDB_1998,"[D-Asp³,ADMAdda5]MC‐RR",,,Microcystin,C49H73N13O13,1052.18,1051.54508,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C49H73N13O13/c1-26(23-27(2)38(75-31(6)63)24-32-13-9-8-10-14-32)17-18-33-28(3)41(66)60-36(46(71)72)19-20-40(65)62(7)30(5)43(68)56-29(4)42(67)59-35(16-12-22-55-49(52)53)45(70)61-37(47(73)74)25-39(64)57-34(44(69)58-33)15-11-21-54-48(50)51/h8-10,13-14,17-18,23,27-29,33-38H,5,11-12,15-16,19-22,24-25H2,1-4,6-7H3,(H,56,68)(H,57,64)(H,58,69)(H,59,67)(H,60,66)(H,61,70)(H,71,72)(H,73,74)(H4,50,51,54)(H4,52,53,55)/b18-17+,26-23+/t27-,28-,29+,33-,34-,35-,36+,37+,38-/m0/s1",WFXCZYYAJSAVET-KZHDJXOLSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8,15-bis(3-guanidinopropyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802391,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,"Stereochemistry assumed based on other MC congeners. Bioaccumulated in lichen. Detected in: Nephroma parile, Peltigera praetextata, Peltigera membranacea, Peltigera hymenina, Peltigera leucophlebia (lichen species). Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_1999,"[Gly1,D-Asp3,ADMAdda5,Dhb7]MC-RHar",,,Microcystin,C49H73N13O13,1052.18,1051.54508,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@@H](NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)CNC(=O)C(=CC)NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)CCCCNC(=N)N,"InChI=1S/C49H73N13O13/c1-6-32-43(68)56-26-41(66)59-35(16-12-22-55-49(52)53)45(70)62-37(47(73)74)25-40(65)58-34(15-10-11-21-54-48(50)51)44(69)60-33(29(4)42(67)61-36(46(71)72)19-20-39(64)57-32)18-17-27(2)23-28(3)38(75-30(5)63)24-31-13-8-7-9-14-31/h6-9,13-14,17-18,23,28-29,33-38H,10-12,15-16,19-22,24-26H2,1-5H3,(H,56,68)(H,57,64)(H,58,65)(H,59,66)(H,60,69)(H,61,67)(H,62,70)(H,71,72)(H,73,74)(H4,50,51,54)(H4,52,53,55)/b18-17+,27-23+,32-6?/t28-,29-,33-,34-,35-,36+,37+,38-/m0/s1",HCOCFOSTEQACBS-MUXJOVKDSA-N,"(8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-2-ethylidene-15-(4-guanidinobutyl)-8-(3-guanidinopropyl)-19-methyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683806,,10.3390/toxins7020493,http://www.mdpi.com/2072-6651/7/2/493,"Further Characterization of Glycine-Containing Microcystins from the McMurdo Dry Valleys of Antarctica;Toxins;7;2;;2015;journalArticle;10.3390/toxins7020493;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Cary, Stephen; Hamilton, David; Holland, Patrick",n.a.,n.a.,n.a.,"field sample, two hydro-terrestrial cyanobacterial mat samples from Miers Valley in the McMurdo Dry Valleys, Antarctica. These samples were obtained from the moist areas in front of Adams Glacier (MVAG1; 78°6'36''S, 163°54'20''E) and Miers Glacier (MVMG1; 78°5'42''S, 163°55'38''E)",From Antarctica. Stereochemistry partially defined by advanced Marfey amino acid analysis
CyanoMetDB_2000,"[Gly1,D-Asp3,ADMAdda5]MC-RHar",,,Microcystin,C49H73N13O13,1052.18,1051.5451,O=C(N(C)C(C(NCC1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C49H73N13O13/c1-27(23-28(2)38(75-31(5)63)24-32-13-8-7-9-14-32)17-18-33-29(3)42(67)60-36(46(71)72)19-20-41(66)62(6)30(4)43(68)56-26-40(65)58-35(16-12-22-55-49(52)53)45(70)61-37(47(73)74)25-39(64)57-34(44(69)59-33)15-10-11-21-54-48(50)51/h7-9,13-14,17-18,23,28-29,33-38H,4,10-12,15-16,19-22,24-26H2,1-3,5-6H3,(H,56,68)(H,57,64)(H,58,65)(H,59,69)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,50,51,54)(H4,52,53,55)/b18-17+,27-23+/t28-,29-,33-,34-,35-,36+,37+,38-/m0/s1",DXQGDFJSROTNES-RFXBWKCSSA-N,"(8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-8-(3-guanidinopropyl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683839,,10.1128/aem.01243-08,http://aem.asm.org/cgi/doi/10.1128/AEM.01243-08,"Widespread Distribution and Identification of Eight Novel Microcystins in Antarctic Cyanobacterial Mats;Applied and Environmental Microbiology;74;23;;2008;journalArticle;10.1128/AEM.01243-08;Wood, S. A.; Mountfort, D.; Selwood, A. I.; Holland, P. T.; Puddick, J.; Cary, S. C.",Nostoc,cyanobacterial mat,n.a.,,From Antarctica. Compound MC-8 in cited reference. Stereochemistry assumed based on other MC congeners.
CyanoMetDB_2001,"[D‐Leu1,Adda(OH)5]MC‐LR","[D‐Leu1,hydroxyAdda5]MC‐LR",,Microcystin,C52H80N10O13,1053.25,1052.5906,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(CO)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C52H80N10O13/c1-28(2)23-39-48(69)60-40(24-29(3)4)49(70)61-43(51(73)74)32(7)45(66)57-37(17-14-22-55-52(53)54)47(68)56-36(19-18-35(27-63)25-30(5)41(75-10)26-34-15-12-11-13-16-34)31(6)44(65)58-38(50(71)72)20-21-42(64)62(9)33(8)46(67)59-39/h11-13,15-16,18-19,25,28-32,36-41,43,63H,8,14,17,20-24,26-27H2,1-7,9-10H3,(H,56,68)(H,57,66)(H,58,65)(H,59,67)(H,60,69)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b19-18+,35-25-/t30-,31-,32-,36-,37-,38+,39+,40-,41-,43+/m0/s1",KUJGVALYAACNLY-DWMFVRHXSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-18-((1E,3Z,5S,6S)-3-(hydroxymethyl)-6-methoxy-5-methyl-7-phenylhepta-1,3-dien-1-yl)-5,8-diisobutyl-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802165,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Location of carbonyl in Adda chain not fully defined: Plausible structure. The accurate m/z indicates oxidation at a CH rather than across a double bond. Compounds CyanoMetDB_1990 and CyanoMetDB_2001 were found together in the same sample, and so are probably related to each other. MS/MS indicates oxidation to have taken place between C-2 and C-8. The most favourable position for oxidation would be an allylic CH. Since the other allylic positions (C-3 and C-8 are tri-substituted and therefore cannot be oxidised to carbonyl groups) one educated guess would be that these compounds are most likely to have been oxidised on the 6-methyl group. The aldehyde derivative would have additional stabilisation through conjugation. It ought also to react with thiols, but that reaction would likely be slow due to steric hindrance."
CyanoMetDB_2002,[D‐Glu(OCH2CH(CH3)OH)6]MC‐LR,[D‐Glu(OC3H6O)6]MC‐LR,,Microcystin,C52H80N10O13,1053.25,1052.590633,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)OCC(C)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H80N10O13/c1-28(2)24-40-49(70)61-43(50(71)72)33(7)45(66)58-38(18-15-23-55-52(53)54)48(69)57-37(20-19-29(3)25-30(4)41(74-11)26-36-16-13-12-14-17-36)32(6)44(65)59-39(51(73)75-27-31(5)63)21-22-42(64)62(10)35(9)47(68)56-34(8)46(67)60-40/h12-14,16-17,19-20,25,28,30-34,37-41,43,63H,9,15,18,21-24,26-27H2,1-8,10-11H3,(H,56,68)(H,57,69)(H,58,66)(H,59,65)(H,60,67)(H,61,70)(H,71,72)(H4,53,54,55)/b20-19+,29-25+/t30-,31?,32-,33-,34+,37-,38-,39+,40-,41-,43+/m0/s1",BIPKFIXFAARAAI-GBMZIOTESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-22-((2-hydroxypropoxy)carbonyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",10418620,,10.1021/jo00117a017,https://pubs.acs.org/doi/abs/10.1021/jo00117a017,"Seven More Microcystins from Homer Lake Cells: Application of the General Method for Structure Assignment of Peptides Containing .alpha.,.beta.-Dehydroamino Acid Unit(s);The Journal of Organic Chemistry;60;12;;1995;journalArticle;10.1021/jo00117a017;Namikoshi, Michio; Sun, Furong; Choi, Byoung Wook; Rinehart, Kenneth L.; Carmichael, Wayne W.; Evans, William R.; Beasley, Val R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria Microcystis aeruginosa,"artefactual (not a natural product). Two stereoisomers exist at C-2 of the 1,2-propanediol moiety bonded (as ester) to D-Glu at position 6. The exact structure of the ester group remain undefined."
CyanoMetDB_2003,[D-Asp3]MC-RW,,,Microcystin,C53H71N11O12,1054.2,1053.528367,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CNC4=C3C=CC=C4)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C53H71N11O12/c1-29(24-30(2)43(76-7)25-34-14-9-8-10-15-34)19-20-37-31(3)46(67)62-40(51(72)73)21-22-45(66)64(6)33(5)48(69)58-32(4)47(68)61-39(18-13-23-56-53(54)55)49(70)63-42(52(74)75)27-44(65)59-41(50(71)60-37)26-35-28-57-38-17-12-11-16-36(35)38/h8-12,14-17,19-20,24,28,30-32,37,39-43,57H,5,13,18,21-23,25-27H2,1-4,6-7H3,(H,58,69)(H,59,65)(H,60,71)(H,61,68)(H,62,67)(H,63,70)(H,72,73)(H,74,75)(H4,54,55,56)/b20-19+,29-24+/t30-,31-,32+,37-,39-,40+,41-,42+,43-/m0/s1",XWXSIKQZRUZBPD-DUJZQNBCSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-((1H-indol-3-yl)methyl)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683814,,10.3390/md17110643,https://www.mdpi.com/1660-3397/17/11/643,"Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling;Marine Drugs;17;11;;2019;journalArticle;10.3390/md17110643;Mallia, Vittoria; Uhlig, Silvio; Rafuse, Cheryl; Meija, Juris; Miles, Christopher O.",Planktothrix,planktonica,NIVA-CYA 544,,
CyanoMetDB_2004,[Dha7]MC‐WR,,,Microcystin,C53H71N11O12,1054.2,1053.528367,O=C(NC(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CNC4=C3C=CC=C4)=O)=O)=O)=O,"InChI=1S/C53H71N11O12/c1-28(24-29(2)42(76-7)25-34-14-9-8-10-15-34)19-20-37-30(3)45(66)62-40(51(72)73)21-22-43(65)58-32(5)47(68)59-33(6)48(69)63-41(26-35-27-57-38-17-12-11-16-36(35)38)50(71)64-44(52(74)75)31(4)46(67)61-39(49(70)60-37)18-13-23-56-53(54)55/h8-12,14-17,19-20,24,27,29-31,33,37,39-42,44,57H,5,13,18,21-23,25-26H2,1-4,6-7H3,(H,58,65)(H,59,68)(H,60,70)(H,61,67)(H,62,66)(H,63,69)(H,64,71)(H,72,73)(H,74,75)(H4,54,55,56)/b20-19+,28-24+/t29-,30-,31-,33+,37-,39-,40+,41-,42-,44+/m0/s1",SPNMYMDESAVWLU-LSYLAYNUSA-N,"8-((1H-indol-3-yl)methyl)-15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802329,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,n.a.,AB2011/53,,MS2 available in the article
CyanoMetDB_2005,[D-Asp3]MC-WR,,,Microcystin,C53H71N11O12,1054.2,1053.528367,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC3=CNC4=C3C=CC=C4)=O)=O)=O)=O,"InChI=1S/C53H71N11O12/c1-29(24-30(2)43(76-7)25-34-14-9-8-10-15-34)19-20-37-31(3)46(67)61-40(51(72)73)21-22-45(66)64(6)33(5)48(69)58-32(4)47(68)62-41(26-35-28-57-38-17-12-11-16-36(35)38)50(71)63-42(52(74)75)27-44(65)59-39(49(70)60-37)18-13-23-56-53(54)55/h8-12,14-17,19-20,24,28,30-32,37,39-43,57H,5,13,18,21-23,25-27H2,1-4,6-7H3,(H,58,69)(H,59,65)(H,60,70)(H,61,67)(H,62,68)(H,63,71)(H,72,73)(H,74,75)(H4,54,55,56)/b20-19+,29-24+/t30-,31-,32+,37-,39-,40+,41-,42+,43-/m0/s1",JFISXJSHBWUTGA-DUJZQNBCSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-8-(1H-indol-3-ylmethyl)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,19-trimethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid",139588249,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,n.a.,AB2011/53,,MS2 available in the article
CyanoMetDB_2006,[DMAdda5]MC‐WR,,,Microcystin,C53H71N11O12,1054.2,1053.528367,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CNC4=C3C=CC=C4)=O)=O)=O)=O,"InChI=1S/C53H71N11O12/c1-28(24-29(2)42(65)25-34-14-9-8-10-15-34)19-20-37-30(3)45(67)61-40(51(73)74)21-22-43(66)64(7)33(6)48(70)58-32(5)47(69)62-41(26-35-27-57-38-17-12-11-16-36(35)38)50(72)63-44(52(75)76)31(4)46(68)60-39(49(71)59-37)18-13-23-56-53(54)55/h8-12,14-17,19-20,24,27,29-32,37,39-42,44,57,65H,6,13,18,21-23,25-26H2,1-5,7H3,(H,58,70)(H,59,71)(H,60,68)(H,61,67)(H,62,69)(H,63,72)(H,73,74)(H,75,76)(H4,54,55,56)/b20-19+,28-24+/t29-,30-,31-,32+,37-,39-,40+,41-,42-,44+/m0/s1",OWWLLCNFDJJXQD-ODXYGVHRSA-N,"8-((1H-indol-3-yl)methyl)-15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802256,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,n.a.,AB2011/53,,MS2 available in the article
CyanoMetDB_2007,[D-Met1]MC-LR,,,Microcystin,C51H78N10O12S,1055.29,1054.552139,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCSC)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C51H78N10O12S/c1-28(2)25-39-48(68)60-42(50(71)72)32(6)44(64)56-36(17-14-23-54-51(52)53)46(66)55-35(19-18-29(3)26-30(4)40(73-9)27-34-15-12-11-13-16-34)31(5)43(63)58-38(49(69)70)20-21-41(62)61(8)33(7)45(65)57-37(22-24-74-10)47(67)59-39/h11-13,15-16,18-19,26,28,30-32,35-40,42H,7,14,17,20-25,27H2,1-6,8-10H3,(H,55,66)(H,56,64)(H,57,65)(H,58,63)(H,59,67)(H,60,68)(H,69,70)(H,71,72)(H4,52,53,54)/b19-18+,29-26+/t30-,31-,32-,35-,36-,37+,38+,39-,40-,42+/m0/s1",DURAMHGSEBPVJH-HIDJONPESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-5-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684769,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Microcystis,sp.,[Microcystis sp.]RST9501,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners. Methionine moiety has assumed stereochemistry."
CyanoMetDB_2008,[D-Leu1]MC-MR,,,Microcystin,C51H78N10O12S,1055.29,1054.552139,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCSC)=O)=O)=O)=O,"InChI=1S/C51H78N10O12S/c1-28(2)25-39-48(68)57-37(22-24-74-10)47(67)60-42(50(71)72)32(6)44(64)56-36(17-14-23-54-51(52)53)46(66)55-35(19-18-29(3)26-30(4)40(73-9)27-34-15-12-11-13-16-34)31(5)43(63)58-38(49(69)70)20-21-41(62)61(8)33(7)45(65)59-39/h11-13,15-16,18-19,26,28,30-32,35-40,42H,7,14,17,20-25,27H2,1-6,8-10H3,(H,55,66)(H,56,64)(H,57,68)(H,58,63)(H,59,65)(H,60,67)(H,69,70)(H,71,72)(H4,52,53,54)/b19-18+,29-26+/t30-,31-,32-,35-,36-,37-,38+,39+,40-,42+/m0/s1",FYIBLVGHTIMAGG-OIGYFXLDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-8-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802056,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ",
CyanoMetDB_2009,"[D-Leu1,NMe-Ser7]MC-LR",,,Microcystin,C52H82N10O13,1055.27,1054.606283,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)CC(C)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C52H82N10O13/c1-28(2)23-38-47(68)59-39(24-29(3)4)48(69)61-43(51(73)74)33(8)45(66)57-36(17-14-22-55-52(53)54)46(67)56-35(19-18-30(5)25-31(6)41(75-10)26-34-15-12-11-13-16-34)32(7)44(65)58-37(50(71)72)20-21-42(64)62(9)40(27-63)49(70)60-38/h11-13,15-16,18-19,25,28-29,31-33,35-41,43,63H,14,17,20-24,26-27H2,1-10H3,(H,56,67)(H,57,66)(H,58,65)(H,59,68)(H,60,70)(H,61,69)(H,71,72)(H,73,74)(H4,53,54,55)/b19-18+,30-25+/t31-,32-,33-,35-,36-,37+,38+,39-,40-,41-,43+/m0/s1",ZRAAKZAFDBKKEG-WCHOLIGGSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683871,,10.1002/rcm.7098,http://doi.wiley.com/10.1002/rcm.7098,"Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - unambiguous assignment of product ions by tandem mass spectrometry: Discovery of microcystins by MS/MS;Rapid Communications in Mass Spectrometry;29;2;;2015;journalArticle;10.1002/rcm.7098;Qi, Yulin; Rosso, Lorena; Sedan, Daniela; Giannuzzi, Leda; Andrinolo, Dario; Volmer, Dietrich A.",Microcystis,aeruginosa,[Microcystis aeruginosa] CAAT 2005-3,,Stereochemistry assumed based on other MC congeners (identification by MS only). Also detected in Peltigera degenii (lichen species)
CyanoMetDB_2010,[Mser7]MC-RR,,,Microcystin,C49H77N13O13,1056.21,1055.5764,O=C(N(C)[C@@H](CO)C(N[C@H](C)C1=O)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C49H77N13O13/c1-26(23-27(2)37(75-7)24-31-13-9-8-10-14-31)17-18-32-28(3)40(65)60-35(46(71)72)19-20-38(64)62(6)36(25-63)45(70)56-30(5)42(67)59-34(16-12-22-55-49(52)53)44(69)61-39(47(73)74)29(4)41(66)58-33(43(68)57-32)15-11-21-54-48(50)51/h8-10,13-14,17-18,23,27-30,32-37,39,63H,11-12,15-16,19-22,24-25H2,1-7H3,(H,56,70)(H,57,68)(H,58,66)(H,59,67)(H,60,65)(H,61,69)(H,71,72)(H,73,74)(H4,50,51,54)(H4,52,53,55)/b18-17+,26-23+/t27-,28-,29-,30+,32-,33-,34-,35+,36-,37-,39+/m0/s1",KHCVWMNMBLYWTO-UCXDALDESA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683859,,10.1016/j.toxicon.2019.06.006,https://linkinghub.elsevier.com/retrieve/pii/S0041010119301795,"Comprehensive multi-technique approach reveals the high diversity of microcystins in field collections and an associated isolate of Microcystis aeruginosa from a Turkish lake;Toxicon;167;;;2019;journalArticle;10.1016/j.toxicon.2019.06.006;Yilmaz, Mete; Foss, Amanda J.; Miles, Christopher O.; Özen, Mihriban; Demir, Nilsun; Balcı, Muharrem; Beach, Daniel G.",Microcystis,aeruginosa,AQUAMEB-24,,Thiol derivatization
CyanoMetDB_2011,MC-LNfk,,,Microcystin,C54H72N8O14,1057.19,1056.516799,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC(C(C=CC=C3)=C3NC=O)=O)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C54H72N8O14/c1-29(2)24-41-52(71)61-46(54(74)75)33(6)48(67)59-42(27-43(64)37-18-14-15-19-39(37)55-28-63)51(70)57-38(21-20-30(3)25-31(4)44(76-10)26-36-16-12-11-13-17-36)32(5)47(66)58-40(53(72)73)22-23-45(65)62(9)35(8)50(69)56-34(7)49(68)60-41/h11-21,25,28-29,31-34,38,40-42,44,46H,8,22-24,26-27H2,1-7,9-10H3,(H,55,63)(H,56,69)(H,57,70)(H,58,66)(H,59,67)(H,60,68)(H,61,71)(H,72,73)(H,74,75)/b21-20+,30-25+/t31-,32-,33-,34+,38-,40+,41-,42-,44-,46+/m0/s1",OAOHFDVVSNPTDA-AGMMBEPNSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(2-(2-formamidophenyl)-2-oxoethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802238,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",n.a.,n.a.,n.a.,,strcuture elucidated from commercial MC-LW standard
CyanoMetDB_2012,[ADMAdda5]MC‐FR,,,Microcystin,C53H72N10O13,1057.2,1056.528033,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C53H72N10O13/c1-29(26-30(2)42(76-35(7)64)28-37-18-13-10-14-19-37)21-22-38-31(3)45(66)60-40(51(72)73)23-24-43(65)63(8)34(6)48(69)57-33(5)47(68)61-41(27-36-16-11-9-12-17-36)50(71)62-44(52(74)75)32(4)46(67)59-39(49(70)58-38)20-15-25-56-53(54)55/h9-14,16-19,21-22,26,30-33,38-42,44H,6,15,20,23-25,27-28H2,1-5,7-8H3,(H,57,69)(H,58,70)(H,59,67)(H,60,66)(H,61,68)(H,62,71)(H,72,73)(H,74,75)(H4,54,55,56)/b22-21+,29-26+/t30-,31-,32-,33+,38-,39-,40+,41-,42-,44+/m0/s1",OXDQKFXDBASUQU-BTFGLNETSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-benzyl-15-(3-guanidinopropyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684740,,10.1094/MPMI-22-6-0695,http://apsjournals.apsnet.org/doi/10.1094/MPMI-22-6-0695,"Microcystin Production in the Tripartite Cyanolichen Peltigera leucophlebia;Molecular Plant-Microbe Interactions;22;6;;2009;journalArticle;10.1094/MPMI-22-6-0695;Kaasalainen, Ulla; Jokela, Jouni; Fewer, David P.; Sivonen, Kaarina; Rikkinen, Jouko",Nostoc,sp.,[Nostoc sp.]UK18,,Stereochemistry inferred based on other MC congeners.
CyanoMetDB_2013,"[D-Asp³,ADMAdda5]MC‐HphR",,,Microcystin,C53H72N10O13,1057.2,1056.528033,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C53H72N10O13/c1-30(27-31(2)43(76-35(6)64)28-37-17-12-9-13-18-37)20-22-38-32(3)46(67)61-41(51(72)73)24-25-45(66)63(7)34(5)48(69)57-33(4)47(68)60-40(23-21-36-15-10-8-11-16-36)50(71)62-42(52(74)75)29-44(65)58-39(49(70)59-38)19-14-26-56-53(54)55/h8-13,15-18,20,22,27,31-33,38-43H,5,14,19,21,23-26,28-29H2,1-4,6-7H3,(H,57,69)(H,58,65)(H,59,70)(H,60,68)(H,61,67)(H,62,71)(H,72,73)(H,74,75)(H4,54,55,56)/b22-20+,30-27+/t31-,32-,33+,38-,39-,40-,41+,42+,43-/m0/s1",ODKCYVGYQFUVCB-ISQUMXADSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802240,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,"Stereochemistry assumed based on other MC congeners. Bioaccumulated in lichen. Identified in Peltigera praetextata, Peltigera membranacea and Peltigera hymenina (lichen species). Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_2014,[D‐MeO-Glu6]MC‐YR ,[D‐Glu(OMe)6]MC‐YR,,Microcystin,C53H74N10O13,1059.21,1058.543683,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C53H74N10O13/c1-29(26-30(2)42(75-8)28-35-14-11-10-12-15-35)17-22-38-31(3)45(66)60-40(52(74)76-9)23-24-43(65)63(7)34(6)48(69)57-33(5)47(68)61-41(27-36-18-20-37(64)21-19-36)50(71)62-44(51(72)73)32(4)46(67)59-39(49(70)58-38)16-13-25-56-53(54)55/h10-12,14-15,17-22,26,30-33,38-42,44,64H,6,13,16,23-25,27-28H2,1-5,7-9H3,(H,57,69)(H,58,70)(H,59,67)(H,60,66)(H,61,68)(H,62,71)(H,72,73)(H4,54,55,56)/b22-17+,29-26+/t30-,31-,32-,33+,38-,39-,40+,41-,42-,44+/m0/s1",SVUNNHQOHLLNGA-OCQZQFOGSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",146683831,,10.1371/journal.pone.0091476,https://dx.plos.org/10.1371/journal.pone.0091476,"Selectivity and Potency of Microcystin Congeners against OATP1B1 and OATP1B3 Expressing Cancer Cells;PLoS ONE;9;3;;2014;journalArticle;10.1371/journal.pone.0091476;Niedermeyer, Timo H. J.; Daily, Abigail; Swiatecka-Hagenbruch, Monika; Moscow, Jeffrey A.",Microcystis,aeruginosa,[Microcystis aeruginosa]CBT 850,,Stereochemistry determined by 2D-NMR.
CyanoMetDB_2015,MC-HtyR ,,,Microcystin,C53H74N10O13,1059.21,1058.543683,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C53H74N10O13/c1-29(27-30(2)42(76-8)28-36-13-10-9-11-14-36)16-22-38-31(3)45(66)61-41(51(72)73)24-25-43(65)63(7)34(6)48(69)57-33(5)47(68)60-40(23-19-35-17-20-37(64)21-18-35)50(71)62-44(52(74)75)32(4)46(67)59-39(49(70)58-38)15-12-26-56-53(54)55/h9-11,13-14,16-18,20-22,27,30-33,38-42,44,64H,6,12,15,19,23-26,28H2,1-5,7-8H3,(H,57,69)(H,58,70)(H,59,67)(H,60,68)(H,61,66)(H,62,71)(H,72,73)(H,74,75)(H4,54,55,56)/b22-16+,29-27+/t30-,31-,32-,33+,38-,39-,40-,41+,42-,44+/m0/s1",YQFCSOPLXLDHPK-CWXGWYCISA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",15160480,,10.1021/tx00023a008,https://pubs.acs.org/doi/abs/10.1021/tx00023a008,"Microcystins from Anabaena flos-aquae NRC 525-17;Chemical Research in Toxicology;4;5;;1991;journalArticle;10.1021/tx00023a008;Harada, Kenichi; Ogawa, Kiyoshi; Kimura, Yukio; Murata, Hideaki; Suzuki, Makoto; Thorn, Patti M.; Evans, William R.; Carmichael, Wayne W.",Anabaena/Dolichospermum,flos aquae,NRC 525-17,,Stereochemisty defined by chiral amino acid analysis
CyanoMetDB_2016,"[D-Asp3,D-MeO-Glu6]MC-HtyR","[D-Asp³,D-Glu(OMe)6]MC‐HtyR",MicrocystinHtyR,Microcystin,C53H74N10O13,1059.21,1058.543683,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C53H74N10O13/c1-30(27-31(2)43(75-7)28-36-13-10-9-11-14-36)16-22-38-32(3)46(67)61-41(52(74)76-8)24-25-45(66)63(6)34(5)48(69)57-33(4)47(68)60-40(23-19-35-17-20-37(64)21-18-35)50(71)62-42(51(72)73)29-44(65)58-39(49(70)59-38)15-12-26-56-53(54)55/h9-11,13-14,16-18,20-22,27,31-33,38-43,64H,5,12,15,19,23-26,28-29H2,1-4,6-8H3,(H,57,69)(H,58,65)(H,59,70)(H,60,68)(H,61,67)(H,62,71)(H,72,73)(H4,54,55,56)/b22-16+,30-27+/t31-,32-,33+,38-,39-,40-,41+,42+,43-/m0/s1",QHVWVRZVAONQRC-IXKKHWRDSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",146684706,DTXSID901016184,10.1007/s00203-004-0711-3,http://link.springer.com/10.1007/s00203-004-0711-3,"Diversity of coexisting Planktothrix (Cyanobacteria) chemotypes deduced by mass spectral analysis of microystins and other oligopeptides;Archives of Microbiology;182;4;;2004;journalArticle;10.1007/s00203-004-0711-3;Welker, Martin; Christiansen, Guntram; von Döhren, Hans",Planktothrix,sp.,"[Planktothrix sp.]Max06, [Planktothrix sp.]Max13",,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_2017,"[D-Ser1,D-Asp³]MC‐HtyR",,,Microcystin,C52H72N10O14,1061.19,1060.522947,O=C(N(C)C(C(N[C@H](CO)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O14/c1-29(25-30(2)42(76-6)26-34-11-8-7-9-12-34)14-20-36-31(3)45(67)59-39(50(72)73)22-23-44(66)62(5)32(4)46(68)61-41(28-63)49(71)58-38(21-17-33-15-18-35(64)19-16-33)48(70)60-40(51(74)75)27-43(65)56-37(47(69)57-36)13-10-24-55-52(53)54/h7-9,11-12,14-16,18-20,25,30-31,36-42,63-64H,4,10,13,17,21-24,26-28H2,1-3,5-6H3,(H,56,65)(H,57,69)(H,58,71)(H,59,67)(H,60,70)(H,61,68)(H,72,73)(H,74,75)(H4,53,54,55)/b20-14+,29-25+/t30-,31-,36-,37-,38-,39+,40+,41+,42-/m0/s1",PCWWISFRULMTMQ-FEHBKQEESA-N,"15-(3-((diaminomethylene)amino)propyl)-5-(hydroxymethyl)-8-(4-hydroxyphenethyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684786,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,MS2 available in the article
CyanoMetDB_2018,[D‐Asp³]MC‐Y(OMe)R,"[MeO-Tyr2,D‐Asp3]MC‐Y(OMe)R",,Microcystin,C52H72N10O14,1061.19,1060.522947,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C(OC)=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O14/c1-28(23-29(2)41(75-7)25-33-13-10-9-11-14-33)16-18-35-30(3)45(66)59-37(50(71)72)19-21-44(65)62(6)32(5)47(68)56-31(4)46(67)60-38(24-34-17-20-40(63)42(26-34)76-8)49(70)61-39(51(73)74)27-43(64)57-36(48(69)58-35)15-12-22-55-52(53)54/h9-11,13-14,16-18,20,23,26,29-31,35-39,41,63H,5,12,15,19,21-22,24-25,27H2,1-4,6-8H3,(H,56,68)(H,57,64)(H,58,69)(H,59,66)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/b18-16+,28-23+/t29-,30-,31+,35-,36-,37+,38-,39+,41-/m0/s1",OTKAUTRTWSXHHC-QRQIOJMRSA-N,"10-(3-((diaminomethylene)amino)propyl)-3-(4-hydroxybenzyl)-13-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-14,21,25-trimethyl-22-methylene-4,8,11,15,20,23,26-heptaoxo-1-oxa-2,5,9,12,16,21,24-heptaazacycloheptacosane-6,17-dicarboxylic acid",155802251,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,n.a.,AB2011/53,,MS2 available in the article. Position of extra OCH2 on Tyr not confirmed.
CyanoMetDB_2019,[DMAdda5]MC‐Y(OMe)R,,,Microcystin,C52H72N10O14,1061.19,1060.522947,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C(OC)=C3)=O)=O)=O)=O,"InChI=1S/C52H72N10O14/c1-27(23-28(2)40(64)25-33-13-10-9-11-14-33)16-18-35-29(3)44(66)59-37(50(72)73)19-21-42(65)62(7)32(6)47(69)56-31(5)46(68)60-38(24-34-17-20-39(63)41(26-34)76-8)49(71)61-43(51(74)75)30(4)45(67)58-36(48(70)57-35)15-12-22-55-52(53)54/h9-11,13-14,16-18,20,23,26,28-31,35-38,40,43,63-64H,6,12,15,19,21-22,24-25H2,1-5,7-8H3,(H,56,69)(H,57,70)(H,58,67)(H,59,66)(H,60,68)(H,61,71)(H,72,73)(H,74,75)(H4,53,54,55)/b18-16+,27-23+/t28-,29-,30-,31+,35-,36-,37+,38-,40-,43+/m0/s1",PIKGDNSGBMJTRE-GQSKQMPZSA-N,"10-(3-((diaminomethylene)amino)propyl)-13-((1E,3E)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-3-(4-hydroxybenzyl)-7,14,21,25-tetramethyl-22-methylene-4,8,11,15,20,23,26-heptaoxo-1-oxa-2,5,9,12,16,21,24-heptaazacycloheptacosane-6,17-dicarboxylic acid",155802264,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,n.a.,AB2011/53,,MS2 available in the article. Position of extra OCH2 on Tyr not confirmed.
CyanoMetDB_2020,[Ser7]MC-HtyR,,,Microcystin,C52H74N10O14,1063.2,1062.538597,O=C(N[C@@H](CO)C(N[C@H](C)C1=O)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H74N10O14/c1-28(25-29(2)41(76-6)26-34-11-8-7-9-12-34)14-20-36-30(3)44(66)61-39(50(72)73)22-23-42(65)57-40(27-63)49(71)56-32(5)46(68)60-38(21-17-33-15-18-35(64)19-16-33)48(70)62-43(51(74)75)31(4)45(67)59-37(47(69)58-36)13-10-24-55-52(53)54/h7-9,11-12,14-16,18-20,25,29-32,36-41,43,63-64H,10,13,17,21-24,26-27H2,1-6H3,(H,56,71)(H,57,65)(H,58,69)(H,59,67)(H,60,68)(H,61,66)(H,62,70)(H,72,73)(H,74,75)(H4,53,54,55)/b20-14+,28-25+/t29-,30-,31-,32+,36-,37-,38-,39+,40-,41-,43+/m0/s1",XDDLLCZTPLZHNO-ZOIKCHQHSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101642109,,10.1021/tx00029a011,https://pubs.acs.org/doi/abs/10.1021/tx00029a011,"Structures of three new homotyrosine-containing microcystins and a new homophenylalanine variant from Anabaena sp. strain 66;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a011;Namikoshi, Michio; Sivonen, Kaarina; Evans, William R.; Carmichael, Wayne W.; Rouhiainen, Leo; Luukkainen, Raija; Rinehart, Kenneth L.",Anabaena,n.a.,[Anabaena sp.]66,,Stereochemistry defined by chiral GC-MS analyses.
CyanoMetDB_2021,"[D-Asp3,Mser7]MC‐HtyR",,,Microcystin,C52H74N10O14,1063.2,1062.538597,O=C(N(C)[C@@H](CO)C(N[C@H](C)C1=O)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H74N10O14/c1-29(25-30(2)42(76-6)26-34-11-8-7-9-12-34)14-20-36-31(3)45(67)60-39(50(72)73)22-23-44(66)62(5)41(28-63)49(71)56-32(4)46(68)59-38(21-17-33-15-18-35(64)19-16-33)48(70)61-40(51(74)75)27-43(65)57-37(47(69)58-36)13-10-24-55-52(53)54/h7-9,11-12,14-16,18-20,25,30-32,36-42,63-64H,10,13,17,21-24,26-28H2,1-6H3,(H,56,71)(H,57,65)(H,58,69)(H,59,68)(H,60,67)(H,61,70)(H,72,73)(H,74,75)(H4,53,54,55)/b20-14+,29-25+/t30-,31-,32+,36-,37-,38-,39+,40+,41-,42-/m0/s1",ULIJDDFJIHXKGH-RPENZYNSSA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683868,,10.1007/s00203-004-0711-3,http://link.springer.com/10.1007/s00203-004-0711-3,"Diversity of coexisting Planktothrix (Cyanobacteria) chemotypes deduced by mass spectral analysis of microystins and other oligopeptides;Archives of Microbiology;182;4;;2004;journalArticle;10.1007/s00203-004-0711-3;Welker, Martin; Christiansen, Guntram; von Döhren, Hans",Planktothrix,sp.,[Planktothrix sp.]Max06,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_2022,[seco‐4/5][D-Asp³]MC‐HtyR,,,Microcystin,C52H74N10O14,1063.2,1062.538597,N[C@@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)[C@H](C)C(N[C@@H](C(O)=O)CCC(N(C)C(C(N[C@H](C)C(N[C@@H](CCC2=CC=C(O)C=C2)C(N[C@@H](C(O)=O)CC(N[C@@H](CCCNC(N)=N)C(O)=O)=O)=O)=O)=O)=C)=O)=O,"InChI=1S/C52H74N10O14/c1-29(26-30(2)42(76-7)27-35-12-9-8-10-13-35)15-21-37(53)31(3)45(66)60-40(50(72)73)23-24-44(65)62(6)33(5)47(68)57-32(4)46(67)59-38(22-18-34-16-19-36(63)20-17-34)48(69)61-41(51(74)75)28-43(64)58-39(49(70)71)14-11-25-56-52(54)55/h8-10,12-13,15-17,19-21,26,30-32,37-42,63H,5,11,14,18,22-25,27-28,53H2,1-4,6-7H3,(H,57,68)(H,58,64)(H,59,67)(H,60,66)(H,61,69)(H,70,71)(H,72,73)(H,74,75)(H4,54,55,56)/b21-15+,29-26+/t30-,31-,32+,37-,38-,39-,40+,41+,42-/m0/s1",AFXPXSUFDIMWIH-QDFQMAEMSA-N,"(29E,31E)-1,28-diamino-34-benzyl-13-(4-hydroxyphenethyl)-1-imino-16,20,27,31,33-pentamethyl-19-methylene-8,12,15,18,21,26-hexaoxo-35-oxa-2,7,11,14,17,20,25-heptaazahexatriaconta-29,31-diene-6,10,24-tricarboxylic acid",146684787,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,MS2 available in the article
CyanoMetDB_2023,"[D‐Asp³,ADMAdda5]MC‐(H4)YR",,,Microcystin,C52H74N10O14,1063.2,1062.538597,O=C(CC[C@@H](NC([C@H]([C@@H](NC([C@@H](NC(C[C@@H](NC([C@H](C[C@]1([H])CC[C@@H](O)C=C1)N2)=O)C(O)=O)=O)CCCNC(N)=N)=O)/C=C/C(C)=C/[C@@H]([C@H](CC3=CC=CC=C3)OC(C)=O)C)C)=O)C(O)=O)N(C(C(N[C@H](C)C2=O)=O)=C)C,"InChI=1S/C52H74N10O14/c1-28(24-29(2)42(76-33(6)63)26-34-12-9-8-10-13-34)15-20-37-30(3)45(67)59-39(50(72)73)21-22-44(66)62(7)32(5)47(69)56-31(4)46(68)60-40(25-35-16-18-36(64)19-17-35)49(71)61-41(51(74)75)27-43(65)57-38(48(70)58-37)14-11-23-55-52(53)54/h8-10,12-13,15-16,18,20,24,29-31,35-42,64H,5,11,14,17,19,21-23,25-27H2,1-4,6-7H3,(H,56,69)(H,57,65)(H,58,70)(H,59,67)(H,60,68)(H,61,71)(H,72,73)(H,74,75)(H4,53,54,55)/b20-15+,28-24+/t29-,30-,31+,35-,36-,37-,38-,39+,40-,41+,42-/m0/s1",XDSNSVDTHKUCHQ-PJNYSIOBSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684741,,10.1094/MPMI-22-6-0695,http://apsjournals.apsnet.org/doi/10.1094/MPMI-22-6-0695,"Microcystin Production in the Tripartite Cyanolichen Peltigera leucophlebia;Molecular Plant-Microbe Interactions;22;6;;2009;journalArticle;10.1094/MPMI-22-6-0695;Kaasalainen, Ulla; Jokela, Jouni; Fewer, David P.; Sivonen, Kaarina; Rikkinen, Jouko",Nostoc,sp.,[Nostoc sp.]UK18,,Stereochemistry inferred based on other MC congeners.
CyanoMetDB_2024,[NMe-Ser7]MC‐RY,[Mser7]MC-RY,,Microcystin,C52H74N10O14,1063.2,1062.538597,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C52H74N10O14/c1-28(24-29(2)41(76-7)26-33-12-9-8-10-13-33)15-20-36-30(3)44(66)59-38(50(72)73)21-22-42(65)62(6)40(27-63)49(71)56-32(5)46(68)58-37(14-11-23-55-52(53)54)47(69)61-43(51(74)75)31(4)45(67)60-39(48(70)57-36)25-34-16-18-35(64)19-17-34/h8-10,12-13,15-20,24,29-32,36-41,43,63-64H,11,14,21-23,25-27H2,1-7H3,(H,56,71)(H,57,70)(H,58,68)(H,59,66)(H,60,67)(H,61,69)(H,72,73)(H,74,75)(H4,53,54,55)/b20-15+,28-24+/t29-,30-,31-,32+,36-,37-,38+,39-,40-,41-,43+/m0/s1",FITCZJBNFWEOSI-SNPRYZSRSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-8-(3-guanidinopropyl)-15-(4-hydroxybenzyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684759,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry assumed based on other MC congeners. Detected in microcystin-containing cyanobacterial bloom samples (20 L) from Mwanza Gulf in Lake Victoria, Tanzania, in 2010. MS2 available in the article"
CyanoMetDB_2025,"[D-Asp³,NMe-Ser7]MC‐YHar","[D-Asp³,MSer7]MC‐YHar",,Microcystin,C52H74N10O14,1063.2,1062.538597,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C52H74N10O14/c1-29(24-30(2)42(76-6)26-33-12-8-7-9-13-33)15-20-36-31(3)45(67)59-38(50(72)73)21-22-44(66)62(5)41(28-63)49(71)56-32(4)46(68)60-39(25-34-16-18-35(64)19-17-34)48(70)61-40(51(74)75)27-43(65)57-37(47(69)58-36)14-10-11-23-55-52(53)54/h7-9,12-13,15-20,24,30-32,36-42,63-64H,10-11,14,21-23,25-28H2,1-6H3,(H,56,71)(H,57,65)(H,58,69)(H,59,67)(H,60,68)(H,61,70)(H,72,73)(H,74,75)(H4,53,54,55)/b20-15+,29-24+/t30-,31-,32+,36-,37-,38+,39-,40+,41-,42-/m0/s1",WNQSOLDTHYPGPX-XAJRVOSRSA-N,"(2S,5R,8S,11R,15S,18S,19S,22R)-15-(4-guanidinobutyl)-8-(4-hydroxybenzyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684776,,10.1371/journal.pone.0091476,https://dx.plos.org/10.1371/journal.pone.0091476,"Selectivity and Potency of Microcystin Congeners against OATP1B1 and OATP1B3 Expressing Cancer Cells;PLoS ONE;9;3;;2014;journalArticle;10.1371/journal.pone.0091476;Niedermeyer, Timo H. J.; Daily, Abigail; Swiatecka-Hagenbruch, Monika; Moscow, Jeffrey A.",Microcystis,aeruginosa,[Microcystis aeruginosa]CBT 850,,Stereochemistry determined by 2D-NMR.
CyanoMetDB_2026,[Mdha-Cys7]MC-RR,MC-RR-cysteine; Mcyst MC-RR-Cys,,Microcystin,C52H82N14O14S,1159.36,1158.585564,O=C(N(C1([H])CSC[C@@H](C(O)=O)N)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C52H82N14O14S/c1-27(23-28(2)39(80-7)24-32-13-9-8-10-14-32)17-18-34-29(3)42(68)64-37(49(76)77)19-20-40(67)66(6)38(26-81-25-33(53)48(74)75)47(73)60-31(5)44(70)63-36(16-12-22-59-52(56)57)46(72)65-41(50(78)79)30(4)43(69)62-35(45(71)61-34)15-11-21-58-51(54)55/h8-10,13-14,17-18,23,28-31,33-39,41H,11-12,15-16,19-22,24-26,53H2,1-7H3,(H,60,73)(H,61,71)(H,62,69)(H,63,70)(H,64,68)(H,65,72)(H,74,75)(H,76,77)(H,78,79)(H4,54,55,58)(H4,56,57,59)/b18-17+,27-23+/t28-,29-,30-,31+,33-,34-,35-,36-,37+,38?,39-,41+/m0/s1",CIJTXBGCXWQIOD-GGAGTBMKSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-amino-2-carboxyethyl)thio)methyl)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802012,,10.1021/tx00029a002,https://pubs.acs.org/doi/abs/10.1021/tx00029a002,"Formation, characterization, and toxicity of the glutathione and cysteine conjugates of toxic heptapeptide microcystins;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a002;Kondo, Fumio; Ikai, Yoshitomo; Oka, Hisao; Okumura, Masanao; Ishikawa, Naohisa; Harada, Kenichi; Matsuura, Kenji; Murata, Hideaki; Suzuki, Makoto",n.a.,n.a.,n.a.,"Parent compound derived from field sample, surface bloom collected from Lake Suwa, Japan","Semisynthetic. Kondo et al. prepared this compound synthetically, but anticipated in biological samples. Stereochemistry at Mdha-Cys undefined in cited literature. All other stereochemical centers assumed based on other MC congeners."
CyanoMetDB_2027,[Mdha-GSH7]MC-RR,MC-RR-GSH,,Microcystin,C59H92N16O18S,1345.52,1344.649621,O=C(N(C1([H])CSC[C@@H](C(NCC(O)=O)=O)NC(CC[C@H](N)C(O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C59H92N16O18S/c1-30(25-31(2)43(93-7)26-35-13-9-8-10-14-35)17-19-37-32(3)48(80)73-40(56(89)90)20-22-45(77)75(6)42(29-94-28-41(51(83)67-27-46(78)79)69-44(76)21-18-36(60)55(87)88)54(86)68-34(5)50(82)72-39(16-12-24-66-59(63)64)53(85)74-47(57(91)92)33(4)49(81)71-38(52(84)70-37)15-11-23-65-58(61)62/h8-10,13-14,17,19,25,31-34,36-43,47H,11-12,15-16,18,20-24,26-29,60H2,1-7H3,(H,67,83)(H,68,86)(H,69,76)(H,70,84)(H,71,81)(H,72,82)(H,73,80)(H,74,85)(H,78,79)(H,87,88)(H,89,90)(H,91,92)(H4,61,62,65)(H4,63,64,66)/b19-17+,30-25+/t31-,32-,33-,34+,36-,37-,38-,39-,40+,41-,42?,43-,47+/m0/s1",OWQLCSFYIFFJLC-YBCHMKSDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-3-((carboxymethyl)amino)-3-oxopropyl)thio)methyl)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802255,,10.1021/tx00029a002,https://pubs.acs.org/doi/abs/10.1021/tx00029a002,"Formation, characterization, and toxicity of the glutathione and cysteine conjugates of toxic heptapeptide microcystins;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a002;Kondo, Fumio; Ikai, Yoshitomo; Oka, Hisao; Okumura, Masanao; Ishikawa, Naohisa; Harada, Kenichi; Matsuura, Kenji; Murata, Hideaki; Suzuki, Makoto",n.a.,n.a.,n.a.,"Parent compound derived from field sample, surface bloom collected from Lake Suwa, Japan","Semisynthetic. Kondo et al. prepared this compound synthetically, but anticipated in biological samples. Stereochemistry at Mdha-GSH undefined in cited literature. All other stereochemical centers assumed based on other MC congeners."
CyanoMetDB_2028,"[D-Leu1,ADMAdda5]MC‐LR ",,,Microcystin,C53H80N10O13,1065.26,1064.590633,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C53H80N10O13/c1-28(2)24-40-49(70)61-41(25-29(3)4)50(71)62-44(52(74)75)33(8)46(67)58-38(18-15-23-56-53(54)55)48(69)57-37(20-19-30(5)26-31(6)42(76-35(10)64)27-36-16-13-12-14-17-36)32(7)45(66)59-39(51(72)73)21-22-43(65)63(11)34(9)47(68)60-40/h12-14,16-17,19-20,26,28-29,31-33,37-42,44H,9,15,18,21-25,27H2,1-8,10-11H3,(H,57,69)(H,58,67)(H,59,66)(H,60,68)(H,61,70)(H,62,71)(H,72,73)(H,74,75)(H4,54,55,56)/b20-19+,30-26+/t31-,32-,33-,37-,38-,39+,40+,41-,42-,44+/m0/s1",AZENLJLWZGXBHX-IPELLMHFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-5,8-diisobutyl-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801642,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,"Stereochemistry assumed based on other MC congeners. Bioaccumulated in lichen. Identified in Nephroma cellulosum, Peltigera evansiana and Peltigera sp. (lichen species). Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_2029,"[Leu1,MeO-Glu6]MC‐HilR","[D-Leu1,Glu(OMe)6]MC-HilR",,Microcystin,C54H84N10O12,1065.3,1064.627019,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)C[C@@H](C)CC)=O)=O)=O)=O,"InChI=1S/C54H84N10O12/c1-13-31(4)28-42-51(71)63-45(52(72)73)35(8)47(67)59-39(20-17-25-57-54(55)56)49(69)58-38(22-21-32(5)27-33(6)43(75-11)29-37-18-15-14-16-19-37)34(7)46(66)60-40(53(74)76-12)23-24-44(65)64(10)36(9)48(68)61-41(26-30(2)3)50(70)62-42/h14-16,18-19,21-22,27,30-31,33-35,38-43,45H,9,13,17,20,23-26,28-29H2,1-8,10-12H3,(H,58,69)(H,59,67)(H,60,66)(H,61,68)(H,62,70)(H,63,71)(H,72,73)(H4,55,56,57)/b22-21+,32-27+/t31-,33-,34-,35-,38-,39-,40+,41+,42-,43-,45+/m0/s1",PZMFYRLMLBDWAA-SJELWDFNSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,12,19-trimethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",146683872,,10.1002/rcm.7098,http://doi.wiley.com/10.1002/rcm.7098,"Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - unambiguous assignment of product ions by tandem mass spectrometry: Discovery of microcystins by MS/MS;Rapid Communications in Mass Spectrometry;29;2;;2015;journalArticle;10.1002/rcm.7098;Qi, Yulin; Rosso, Lorena; Sedan, Daniela; Giannuzzi, Leda; Andrinolo, Dario; Volmer, Dietrich A.",Microcystis,aeruginosa,[Microcystis aeruginosa]CAAT 2005-3,,Stereochemistry assumed based on other MC congeners. Also detected in Peltigera degenii (lichen species)
CyanoMetDB_2030,"[D‐Asp3,(E)‐Dhb7]MC‐HtyHty",,,Microcystin,C56H71N7O14,1066.2,1065.5059,O=C(N/C(C(N[C@@H](C1=O)C)=O)=C/C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCC3=CC=C(O)C=C3)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC4=CC=C(O)C=C4)=O)=O)=O)=O,"InChI=1S/C56H71N7O14/c1-7-41-52(70)57-35(5)51(69)61-44(26-19-37-16-22-40(65)23-17-37)54(72)63-46(56(75)76)31-49(67)59-43(25-18-36-14-20-39(64)21-15-36)53(71)60-42(34(4)50(68)62-45(55(73)74)27-28-48(66)58-41)24-13-32(2)29-33(3)47(77-6)30-38-11-9-8-10-12-38/h7-17,20-24,29,33-35,42-47,64-65H,18-19,25-28,30-31H2,1-6H3,(H,57,70)(H,58,66)(H,59,67)(H,60,71)(H,61,69)(H,62,68)(H,63,72)(H,73,74)(H,75,76)/b24-13+,32-29+,41-7+/t33-,34-,35+,42-,43-,44-,45+,46+,47-/m0/s1",DGGUSUVUIGDKFF-VABYWWARSA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-2-ethylidene-8,15-bis(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802029,,10.1021/np800397u,https://pubs.acs.org/doi/10.1021/np800397u,"Isolation and Structure Determination of Two Microcystins and Sequence Comparison of the McyABC Adenylation Domains in Planktothrix Species;Journal of Natural Products;71;11;;2008;journalArticle;10.1021/np800397u;Christiansen, Guntram; Yoshida, Wesley Y.; Blom, Judith F.; Portmann, Cyril; Gademann, Karl; Hemscheidt, Thomas; Kurmayer, Rainer",Planktothrix,rubescens,[Planktothrix rubescens]80,,Thoroughly characterised by complementary techniques.
CyanoMetDB_2031,"[D-Asp3,ADMAdda5,(E/Z)-Dhb7]MC-RR","[D-Asp3,ADMAdda5,Dhb7]MC-RR",,Microcystin,C49H73N13O13,1052.18,1051.54508,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)NC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C49H73N13O13/c1-7-32-43(68)56-29(5)42(67)60-35(16-12-22-55-49(52)53)45(70)62-37(47(73)74)25-40(65)58-34(15-11-21-54-48(50)51)44(69)59-33(28(4)41(66)61-36(46(71)72)19-20-39(64)57-32)18-17-26(2)23-27(3)38(75-30(6)63)24-31-13-9-8-10-14-31/h7-10,13-14,17-18,23,27-29,33-38H,11-12,15-16,19-22,24-25H2,1-6H3,(H,56,68)(H,57,64)(H,58,65)(H,59,69)(H,60,67)(H,61,66)(H,62,70)(H,71,72)(H,73,74)(H4,50,51,54)(H4,52,53,55)/b18-17+,26-23+,32-7?/t27-,28-,29+,33-,34-,35-,36+,37+,38-/m0/s1",XHKHVZRIQATICZ-RYPFVCKKSA-N,"(5R,8S,11R,15S,18S,19S,22R,Z)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-2-ethylidene-8,15-bis(3-guanidinopropyl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",139583100,,10.1016/S0031-9422(97)00769-3,https://linkinghub.elsevier.com/retrieve/pii/S0031942297007693,"Three dehydrobutyrine-containing microcystins from Nostoc;Phytochemistry;47;7;;1998;journalArticle;10.1016/S0031-9422(97)00769-3;Beattie, Kenneth A.; Kaya, Kunimitsu; Sano, Tomoharu; Codd, Geoffrey A.",Nostoc,sp.,[Nostoc sp.]DUN901,,"Chirality of Dhb undefined, but all other amino acid chiralities assigned by NMR and chiral GC-MS analyses."
CyanoMetDB_2032,MC-HarHar,,,Microcystin,C51H79N13O12,1066.25,1065.597115,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C51H79N13O12/c1-28(26-29(2)39(76-8)27-34-16-10-9-11-17-34)20-21-35-30(3)42(66)62-38(48(72)73)22-23-40(65)64(7)33(6)45(69)58-32(5)44(68)61-37(19-13-15-25-57-51(54)55)47(71)63-41(49(74)75)31(4)43(67)60-36(46(70)59-35)18-12-14-24-56-50(52)53/h9-11,16-17,20-21,26,29-32,35-39,41H,6,12-15,18-19,22-25,27H2,1-5,7-8H3,(H,58,69)(H,59,70)(H,60,67)(H,61,68)(H,62,66)(H,63,71)(H,72,73)(H,74,75)(H4,52,53,56)(H4,54,55,57)/b21-20+,28-26+/t29-,30-,31-,32+,35-,36-,37-,38+,39-,41+/m0/s1",FNBUXGYDJOQZPB-IBUOYHJBSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(4-guanidinobutyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683866,,10.1016/j.bbrc.2006.03.199,https://linkinghub.elsevier.com/retrieve/pii/S0006291X06007662,"Use of electrospray tandem mass spectrometry for identification of microcystins during a cyanobacterial bloom event;Biochemical and Biophysical Research Communications;344;3;;2006;journalArticle;10.1016/j.bbrc.2006.03.199;Frias, Humberto Vieira; Mendes, Maria Anita; Cardozo, Karina Helena Morais; Carvalho, Valdemir Melechco; Tomazela, Daniela; Colepicolo, Pio; Pinto, Ernani",n.a.,sp.,n.a.,"field sample, Billings reservoir (Sa˜o Paulo City, 23 deg. 50' 41'' S, 46 deg. 39' 25'' W, Fig. 2) (October 2003)- multiple species, including Microcystis aeruginosa, Microcystis novacekii, Microcystis panniforms, Microcystis protocystis, Planktothrix agardhii, Radiocystis fernandoi, Pseudanabaena mucicol and Cylindrospermopsis raciborskii.","Detected in cyanobacteria samples collected from Billings reservoir (São Paulo). Colonies consisted predominantly of Microcystis aeruginosa, Microcystis novacekii, Microcystis panniforms, Microcystis protocystis, Planktothrix agardhii, Radiocystis fernandoi, Pseudanabaena mucicola and Cylindrospermopsis raciborskii"
CyanoMetDB_2033,"[D-Leu1,D-Asp3]MC-RR",,,Microcystin,C51H79N13O12,1066.25,1065.597115,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C51H79N13O12/c1-28(2)24-38-47(71)60-36(17-13-23-57-51(54)55)46(70)63-39(49(74)75)27-41(65)58-35(16-12-22-56-50(52)53)45(69)59-34(19-18-29(3)25-30(4)40(76-8)26-33-14-10-9-11-15-33)31(5)43(67)61-37(48(72)73)20-21-42(66)64(7)32(6)44(68)62-38/h9-11,14-15,18-19,25,28,30-31,34-40H,6,12-13,16-17,20-24,26-27H2,1-5,7-8H3,(H,58,65)(H,59,69)(H,60,71)(H,61,67)(H,62,68)(H,63,70)(H,72,73)(H,74,75)(H4,52,53,56)(H4,54,55,57)/b19-18+,29-25+/t30-,31-,34-,35-,36-,37+,38+,39+,40-/m0/s1",UITNVKFCFUVOFG-JAQPLRKGSA-N,"(5R,8S,11R,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684770,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Phormidium,sp.,[Phormidium sp.]CENA270,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_2034,MC-WR,,,Microcystin,C54H73N11O12,1068.22,1067.544017,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CNC4=C3C=CC=C4)=O)=O)=O)=O,"InChI=1S/C54H73N11O12/c1-29(25-30(2)43(77-8)26-35-15-10-9-11-16-35)20-21-38-31(3)46(67)62-41(52(73)74)22-23-44(66)65(7)34(6)49(70)59-33(5)48(69)63-42(27-36-28-58-39-18-13-12-17-37(36)39)51(72)64-45(53(75)76)32(4)47(68)61-40(50(71)60-38)19-14-24-57-54(55)56/h9-13,15-18,20-21,25,28,30-33,38,40-43,45,58H,6,14,19,22-24,26-27H2,1-5,7-8H3,(H,59,70)(H,60,71)(H,61,68)(H,62,67)(H,63,69)(H,64,72)(H,73,74)(H,75,76)(H4,55,56,57)/b21-20+,29-25+/t30-,31-,32-,33+,38-,40-,41+,42-,43-,45+/m0/s1",UGNOHFGJSOFQHC-ZISXDMAXSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-((1H-indol-3-yl)methyl)-15-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",101619976,,10.1021/jo00029a016,https://pubs.acs.org/doi/abs/10.1021/jo00029a016,"Identification of 12 hepatotoxins from a Homer Lake bloom of the cyanobacteria Microcystis aeruginosa, Microcystis viridis, and Microcystis wesenbergii: nine new microcystins;The Journal of Organic Chemistry;57;3;;1992;journalArticle;10.1021/jo00029a016;Namikoshi, Michio; Rinehart, Kenneth L.; Sakai, Ryuichi; Stotts, Richard R.; Dahlem, Andrew M.; Beasley, Val R.; Carmichael, Wayne W.; Evans, William R.",n.a.,n.a.,n.a.,field sample; Homer Lake Bloom of the Cyanobacteria Microcystis aeruginosa (also contained Microcystis viridis and Microcystis wesenbergii),"Stereochemistry of Trp moiety is assumed. Detected in field samples collected from Homer Lake (Illinois), consisted primarily of M. aeruginosa plus smaller quantities of M. uiridis and M. wesenbergii."
CyanoMetDB_2035,"[D-Leu1,D-MeO-Glu6,NMe-Ser7]MC‐LR","[D-Leu1,D-Glu(OMe)6,Mser7]MC-LR",MicrocystinWR,Microcystin,C53H84N10O13,1069.29,1068.621933,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)CC(C)C)=O)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C53H84N10O13/c1-29(2)24-39-48(69)60-40(25-30(3)4)49(70)62-44(51(72)73)34(8)46(67)58-37(18-15-23-56-53(54)55)47(68)57-36(20-19-31(5)26-32(6)42(75-10)27-35-16-13-12-14-17-35)33(7)45(66)59-38(52(74)76-11)21-22-43(65)63(9)41(28-64)50(71)61-39/h12-14,16-17,19-20,26,29-30,32-34,36-42,44,64H,15,18,21-25,27-28H2,1-11H3,(H,57,68)(H,58,67)(H,59,66)(H,60,69)(H,61,71)(H,62,70)(H,72,73)(H4,54,55,56)/b20-19+,31-26+/t32-,33-,34-,36-,37-,38+,39+,40-,41-,42-,44+/m0/s1",CABXVCHSKOMXQY-OLDNHBKMSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",146683873,DTXSID101016178,10.1002/rcm.7098,http://doi.wiley.com/10.1002/rcm.7098,"Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - unambiguous assignment of product ions by tandem mass spectrometry: Discovery of microcystins by MS/MS;Rapid Communications in Mass Spectrometry;29;2;;2015;journalArticle;10.1002/rcm.7098;Qi, Yulin; Rosso, Lorena; Sedan, Daniela; Giannuzzi, Leda; Andrinolo, Dario; Volmer, Dietrich A.",Microcystis,aeruginosa,[Microcystis aeruginosa] CAAT 2005-3,,Stereochemistry assumed based on other MC congeners (identification by MS only). Also detected in Peltigera degenii (lichen species)
CyanoMetDB_2036,[D-Met(O)1]MC-LR,[M(O)1]MC‐LR,,Microcystin,C51H78N10O13S,1071.29,1070.547054,O=C(N(C)C(C(N[C@@H](C1=O)CCS(C)=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C51H78N10O13S/c1-28(2)25-39-48(68)60-42(50(71)72)32(6)44(64)56-36(17-14-23-54-51(52)53)46(66)55-35(19-18-29(3)26-30(4)40(74-9)27-34-15-12-11-13-16-34)31(5)43(63)58-38(49(69)70)20-21-41(62)61(8)33(7)45(65)57-37(47(67)59-39)22-24-75(10)73/h11-13,15-16,18-19,26,28,30-32,35-40,42H,7,14,17,20-25,27H2,1-6,8-10H3,(H,55,66)(H,56,64)(H,57,65)(H,58,63)(H,59,67)(H,60,68)(H,69,70)(H,71,72)(H4,52,53,54)/b19-18+,29-26+/t30-,31-,32-,35-,36-,37+,38+,39-,40-,42+,75?/m0/s1",FYGVSVGVTBXKSQ-ZKCOOUHSSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-5-(2-(methylsulfinyl)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683874,,10.1002/rcm.7098,http://doi.wiley.com/10.1002/rcm.7098,"Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - unambiguous assignment of product ions by tandem mass spectrometry: Discovery of microcystins by MS/MS;Rapid Communications in Mass Spectrometry;29;2;;2015;journalArticle;10.1002/rcm.7098;Qi, Yulin; Rosso, Lorena; Sedan, Daniela; Giannuzzi, Leda; Andrinolo, Dario; Volmer, Dietrich A.",Microcystis,aeruginosa,[Microcystis aeruginosa] CAAT 2005-3,,Stereochemistry assumed based on other MC congeners (identification by MS only). Also detected in Peltigera degenii (lichen species)
CyanoMetDB_2037,[D-Leu1]MC‐M(O)R,,,Microcystin,C51H78N10O13S,1071.3,1070.547054,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCS(C)=O)=O)=O)=O)=O,"InChI=1S/C51H78N10O13S/c1-28(2)25-39-48(68)57-37(22-24-75(10)73)47(67)60-42(50(71)72)32(6)44(64)56-36(17-14-23-54-51(52)53)46(66)55-35(19-18-29(3)26-30(4)40(74-9)27-34-15-12-11-13-16-34)31(5)43(63)58-38(49(69)70)20-21-41(62)61(8)33(7)45(65)59-39/h11-13,15-16,18-19,26,28,30-32,35-40,42H,7,14,17,20-25,27H2,1-6,8-10H3,(H,55,66)(H,56,64)(H,57,68)(H,58,63)(H,59,65)(H,60,67)(H,69,70)(H,71,72)(H4,52,53,54)/b19-18+,29-26+/t30-,31-,32-,35-,36-,37-,38+,39+,40-,42+,75?/m0/s1",GFBBOSQXMYDYED-UNRDJFFOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-8-(2-(methylsulfinyl)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802060,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",Microcystis,aeruginosa,bloom,,"Also CPCC-464, racemic at sulfur, from autoxidation of [D-Leu1]MC-MR"
CyanoMetDB_2038,"[D-Leu1,D-Asp³]MC‐HphR",,,Microcystin,C55H78N10O12,1071.27,1070.580068,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C55H78N10O12/c1-32(2)28-43-52(72)61-41(24-22-37-16-11-9-12-17-37)51(71)64-44(54(75)76)31-46(66)59-40(20-15-27-58-55(56)57)50(70)60-39(23-21-33(3)29-34(4)45(77-8)30-38-18-13-10-14-19-38)35(5)48(68)62-42(53(73)74)25-26-47(67)65(7)36(6)49(69)63-43/h9-14,16-19,21,23,29,32,34-35,39-45H,6,15,20,22,24-28,30-31H2,1-5,7-8H3,(H,59,66)(H,60,70)(H,61,72)(H,62,68)(H,63,69)(H,64,71)(H,73,74)(H,75,76)(H4,56,57,58)/b23-21+,33-29+/t34-,35-,39-,40-,41-,42+,43+,44+,45-/m0/s1",BXORURFXTQUPSQ-IEPLTTJDSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,19-dimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801671,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,"Stereochemistry assumed based on other MC congeners. Bioaccumulated in lichen. Identified in Peltigera degenii (lichen species). Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_2039,[D-Phe1]MC‐LR,,,Microcystin,C55H78N10O12,1071.27,1070.580068,O=C(N(C)C(C(N[C@@H](C1=O)CC2=CC=CC=C2)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC3=CC=CC=C3)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C55H78N10O12/c1-31(2)27-42-52(72)64-46(54(75)76)35(6)48(68)60-40(21-16-26-58-55(56)57)50(70)59-39(23-22-32(3)28-33(4)44(77-9)30-38-19-14-11-15-20-38)34(5)47(67)61-41(53(73)74)24-25-45(66)65(8)36(7)49(69)62-43(51(71)63-42)29-37-17-12-10-13-18-37/h10-15,17-20,22-23,28,31,33-35,39-44,46H,7,16,21,24-27,29-30H2,1-6,8-9H3,(H,59,70)(H,60,68)(H,61,67)(H,62,69)(H,63,71)(H,64,72)(H,73,74)(H,75,76)(H4,56,57,58)/b23-22+,32-28+/t33-,34-,35-,39-,40-,41+,42-,43+,44-,46+/m0/s1",WSMOZMQKQAHELG-LONBYMFTSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-5-benzyl-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684771,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Microcystis,aeruginosa,[Microcystis sp.]NPLJ-4,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_2040,[D-Leu1]MC‐FR,,,Microcystin,C55H78N10O12,1071.26,1070.580068,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C55H78N10O12/c1-31(2)27-42-51(71)63-43(29-37-17-12-10-13-18-37)52(72)64-46(54(75)76)35(6)48(68)60-40(21-16-26-58-55(56)57)50(70)59-39(23-22-32(3)28-33(4)44(77-9)30-38-19-14-11-15-20-38)34(5)47(67)61-41(53(73)74)24-25-45(66)65(8)36(7)49(69)62-42/h10-15,17-20,22-23,28,31,33-35,39-44,46H,7,16,21,24-27,29-30H2,1-6,8-9H3,(H,59,70)(H,60,68)(H,61,67)(H,62,69)(H,63,71)(H,64,72)(H,73,74)(H,75,76)(H4,56,57,58)/b23-22+,32-28+/t33-,34-,35-,39-,40-,41+,42+,43-,44-,46+/m0/s1",OWZKCYUKKHQPDU-JCBPHERESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802257,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ",Also CPCC-464
CyanoMetDB_2041,MC‐KynR,MC‐KynR (oxidised W),,Microcystin,C53H73N11O13,1072.21,1071.538932,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C(C=CC=C3)=C3N)=O)=O)=O)=O)=O,"InChI=1S/C53H73N11O13/c1-28(25-29(2)42(77-8)26-34-15-10-9-11-16-34)20-21-37-30(3)45(67)61-39(51(73)74)22-23-43(66)64(7)33(6)48(70)58-32(5)47(69)62-40(27-41(65)35-17-12-13-18-36(35)54)50(72)63-44(52(75)76)31(4)46(68)60-38(49(71)59-37)19-14-24-57-53(55)56/h9-13,15-18,20-21,25,29-32,37-40,42,44H,6,14,19,22-24,26-27,54H2,1-5,7-8H3,(H,58,70)(H,59,71)(H,60,68)(H,61,67)(H,62,69)(H,63,72)(H,73,74)(H,75,76)(H4,55,56,57)/b21-20+,28-25+/t29-,30-,31-,32+,37-,38-,39+,40-,42-,44+/m0/s1",UGTOBXTXSTVUSN-UKFGIZBISA-N,"8-(2-(2-aminophenyl)-2-oxoethyl)-15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683827,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,n.a.,CAWBG11,," MS/MS with Bruker AmaZon X ESI MS, HRMS with Bruker MicrOTOF MS"
CyanoMetDB_2042,"[D-Asp3,ADMAdda5]MC-HtyR",,,Microcystin,C53H72N10O14,1073.2,1072.522947,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C53H72N10O14/c1-29(26-30(2)43(77-34(6)64)27-36-12-9-8-10-13-36)15-21-38-31(3)46(68)61-41(51(73)74)23-24-45(67)63(7)33(5)48(70)57-32(4)47(69)60-40(22-18-35-16-19-37(65)20-17-35)50(72)62-42(52(75)76)28-44(66)58-39(49(71)59-38)14-11-25-56-53(54)55/h8-10,12-13,15-17,19-21,26,30-32,38-43,65H,5,11,14,18,22-25,27-28H2,1-4,6-7H3,(H,57,70)(H,58,66)(H,59,71)(H,60,69)(H,61,68)(H,62,72)(H,73,74)(H,75,76)(H4,54,55,56)/b21-15+,29-26+/t30-,31-,32+,38-,39-,40-,41+,42+,43-/m0/s1",NHGHJQQZDIDSCY-SNWASLKVSA-N,"(5R,8S,11R,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684700,,10.1002/tox.10042,http://doi.wiley.com/10.1002/tox.10042,"[ADMAdda5]-microcystins in Planktothrix agardhii strain PH-123 (cyanobacteria)? importance for monitoring of microcystins in the environment;Environmental Toxicology;17;4;;2002;journalArticle;10.1002/tox.10042;Laub, Jesper; Henriksen, Peter; Brittain, Scott M.; Wang, Jim; Carmichael, Wayne W.; Rinehart, Kenneth L.; Moestrup, �jvind",Oscillatoria/Planktothrix,agardhii,[Oscillatoria/Planktothrix agardhii]PH-123,,"The cited reference was not able to distinguish Mdha and Dhb based on the approaches applied. Hence, building block 7 is assumed to be Mdha. Stereochemistry is assumed based on other MC congeners."
CyanoMetDB_2043,"[D-Asp3,ADMAdda5,(E/Z)-Dhb7]MC-HtyR",,,Microcystin,C53H72N10O14,1073.2,1072.522947,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)C[C@@H](NC(=O)[C@H](CCc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C\C)\NC(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C53H72N10O14/c1-7-37-48(70)57-32(5)47(69)61-40(22-18-34-16-19-36(65)20-17-34)50(72)63-42(52(75)76)28-45(67)59-39(14-11-25-56-53(54)55)49(71)60-38(31(4)46(68)62-41(51(73)74)23-24-44(66)58-37)21-15-29(2)26-30(3)43(77-33(6)64)27-35-12-9-8-10-13-35/h7-10,12-13,15-17,19-21,26,30-32,38-43,65H,11,14,18,22-25,27-28H2,1-6H3,(H,57,70)(H,58,66)(H,59,67)(H,60,71)(H,61,69)(H,62,68)(H,63,72)(H,73,74)(H,75,76)(H4,54,55,56)/b21-15+,29-26+,37-7?/t30-,31-,32+,38-,39-,40-,41+,42+,43-/m0/s1",QOBIMFYINUFCSC-AKJAINAWSA-N,"(5R,8S,11R,15S,18S,19S,22R,Z)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-2-ethylidene-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",139587478,,10.1016/S0031-9422(97)00769-3,https://linkinghub.elsevier.com/retrieve/pii/S0031942297007693,"Three dehydrobutyrine-containing microcystins from Nostoc;Phytochemistry;47;7;;1998;journalArticle;10.1016/S0031-9422(97)00769-3;Beattie, Kenneth A.; Kaya, Kunimitsu; Sano, Tomoharu; Codd, Geoffrey A.",Nostoc,sp.,[Nostoc sp.]DUN901,,"Chirality of Dhb undefined, but all other amino acid chiralities assigned by NMR and chiral GC-MS analyses."
CyanoMetDB_2044,[ADMAdda5]MC‐YR,,,Microcystin,C53H72N10O14,1073.2,1072.522947,CC(=O)O[C@@H](Cc1ccccc1)[C@@H](C)\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O,"InChI=1S/C53H72N10O14/c1-28(25-29(2)42(77-34(7)64)27-35-13-10-9-11-14-35)16-21-38-30(3)45(67)60-40(51(73)74)22-23-43(66)63(8)33(6)48(70)57-32(5)47(69)61-41(26-36-17-19-37(65)20-18-36)50(72)62-44(52(75)76)31(4)46(68)59-39(49(71)58-38)15-12-24-56-53(54)55/h9-11,13-14,16-21,25,29-32,38-42,44,65H,6,12,15,22-24,26-27H2,1-5,7-8H3,(H,57,70)(H,58,71)(H,59,68)(H,60,67)(H,61,69)(H,62,72)(H,73,74)(H,75,76)(H4,54,55,56)/b21-16+,28-25+/t29-,30-,31-,32+,38-,39-,40+,41-,42-,44+/m0/s1",MWAORMUJMWTHOO-MIODMMCSSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684733,,10.1186/1471-2148-7-183,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-7-183,"Recurrent adenylation domain replacement in the microcystin synthetase gene cluster;BMC Evolutionary Biology;7;1;;2007;journalArticle;10.1186/1471-2148-7-183;Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Laakso, Kati; Wang, Hao; Sivonen, Kaarina",Nostoc,sp.,[Nostoc sp.]IO-102-I,,Stereochemistry assumed based on other MC congeners.
CyanoMetDB_2045,MC‐MhtyR,,,Microcystin,C54H76N10O13,1073.24,1072.559333,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1C)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C54H76N10O13/c1-30(28-31(2)43(77-9)29-37-14-11-10-12-15-37)17-23-39-32(3)46(67)61-41(52(73)74)24-26-44(66)63(7)35(6)48(69)58-34(5)51(72)64(8)42(25-20-36-18-21-38(65)22-19-36)50(71)62-45(53(75)76)33(4)47(68)60-40(49(70)59-39)16-13-27-57-54(55)56/h10-12,14-15,17-19,21-23,28,31-34,39-43,45,65H,6,13,16,20,24-27,29H2,1-5,7-9H3,(H,58,69)(H,59,70)(H,60,68)(H,61,67)(H,62,71)(H,73,74)(H,75,76)(H4,55,56,57)/b23-17+,30-28+/t31-,32-,33-,34+,39-,40-,41+,42-,43-,45+/m0/s1",DRRSPCNUSAQJEE-IGXABBBVSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,7,12,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683851,,10.1021/acs.est.5b04415,https://pubs.acs.org/doi/10.1021/acs.est.5b04415,"Combined LC–MS/MS and Molecular Networking Approach Reveals New Cyanotoxins from the 2014 Cyanobacterial Bloom in Green Lake, Seattle;Environmental Science & Technology;49;24;;2015;journalArticle;10.1021/acs.est.5b04415;Teta, Roberta; Della Sala, Gerardo; Glukhov, Evgenia; Gerwick, Lena; Gerwick, William H.; Mangoni, Alfonso; Costantino, Valeria",n.a.,aeruginosa,[Microcystis aeruginosa]SEAGL14,"field sample, primarily Microcystis aeruginosa","Detected in a sample of cyanobacterial scum collected at Green Lake, Seattle. Stereochemistry assumed based on other MC congeners."
CyanoMetDB_2046,"[D-Asp3,(E)‐Dhb7]MC‐HtyW","[D-Asp3,Dhb7]MC-HtyW",,Microcystin,C57H70N8O13,1075.21,1074.506235,O=C(N/C(C(N[C@@H](C1=O)C)=O)=C/C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CNC4=C3C=CC=C4)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC5=CC=C(O)C=C5)=O)=O)=O)=O,"InChI=1S/C57H70N8O13/c1-7-41-53(71)59-35(5)52(70)63-44(24-20-36-18-21-39(66)22-19-36)54(72)65-47(57(76)77)30-50(68)61-46(29-38-31-58-43-16-12-11-15-40(38)43)55(73)62-42(34(4)51(69)64-45(56(74)75)25-26-49(67)60-41)23-17-32(2)27-33(3)48(78-6)28-37-13-9-8-10-14-37/h7-19,21-23,27,31,33-35,42,44-48,58,66H,20,24-26,28-30H2,1-6H3,(H,59,71)(H,60,67)(H,61,68)(H,62,73)(H,63,70)(H,64,69)(H,65,72)(H,74,75)(H,76,77)/b23-17+,32-27+,41-7+/t33-,34-,35+,42-,44-,45+,46-,47+,48-/m0/s1",AQBLNSUXUYUERE-KDEIUMRESA-N,"(5R,8S,11R,15S,18S,19S,22R,E)-15-((1H-indol-3-yl)methyl)-2-ethylidene-8-(4-hydroxyphenethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-5,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684778,,10.1007/s13659-013-0001-3,http://link.springer.com/10.1007/s13659-013-0001-3,"Isolation of Microcystins from the Cyanobacterium Planktothrix rubescens Strain No80;Natural Products and Bioprospecting;4;1;;2014;journalArticle;10.1007/s13659-013-0001-3;Niedermeyer, Timo H. J.; Schmieder, Peter; Kurmayer, Rainer",Oscillatoria/Planktothrix,rubescens,80,,"Stereochemistry assumed based on relative MC congeners, synthesised by the same synthetase enzyme."
CyanoMetDB_2047,MC‐RY(OMe),,,Microcystin,C53H74N10O14,1075.21,1074.538597,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C(OC)=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C53H74N10O14/c1-28(24-29(2)41(76-8)26-34-14-11-10-12-15-34)17-19-36-30(3)45(66)60-38(51(72)73)20-22-43(65)63(7)33(6)48(69)57-32(5)47(68)59-37(16-13-23-56-53(54)55)49(70)62-44(52(74)75)31(4)46(67)61-39(50(71)58-36)25-35-18-21-40(64)42(27-35)77-9/h10-12,14-15,17-19,21,24,27,29-32,36-39,41,44,64H,6,13,16,20,22-23,25-26H2,1-5,7-9H3,(H,57,69)(H,58,71)(H,59,68)(H,60,66)(H,61,67)(H,62,70)(H,72,73)(H,74,75)(H4,54,55,56)/b19-17+,28-24+/t29-,30-,31-,32+,36-,37-,38+,39-,41-,44+/m0/s1",KVGCOYJJGOCUHW-IQEZPTFASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(3-guanidinopropyl)-15-(4-hydroxy-3-methoxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684760,,10.1016/j.toxicon.2013.03.016,https://linkinghub.elsevier.com/retrieve/pii/S0041010113001116,"Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC–MS with thiol derivatization;Toxicon;70;;;2013;journalArticle;10.1016/j.toxicon.2013.03.016;Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Rundberget, Thomas; Wilkins, Alistair L.; Rise, Frode; Ballot, Andreas",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry assumed based on other MC congeners. Location of methylation on tyrosine is assumed. Detected in microcystin-containing cyanobacterial bloom samples (20 L) from Mwanza Gulf in Lake Victoria, Tanzania, in 2010. MS2 available in the article."
CyanoMetDB_2048,[D-Asp³]MC‐Htyr(OMe)R,,,Microcystin,C53H74N10O14,1075.21,1074.538597,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C(OC)=C3)=O)=O)=O)=O,"InChI=1S/C53H74N10O14/c1-29(25-30(2)42(76-7)26-34-13-10-9-11-14-34)16-19-36-31(3)46(67)61-39(51(72)73)21-23-45(66)63(6)33(5)48(69)57-32(4)47(68)60-38(20-17-35-18-22-41(64)43(27-35)77-8)50(71)62-40(52(74)75)28-44(65)58-37(49(70)59-36)15-12-24-56-53(54)55/h9-11,13-14,16,18-19,22,25,27,30-32,36-40,42,64H,5,12,15,17,20-21,23-24,26,28H2,1-4,6-8H3,(H,57,69)(H,58,65)(H,59,70)(H,60,68)(H,61,67)(H,62,71)(H,72,73)(H,74,75)(H4,54,55,56)/b19-16+,29-25+/t30-,31-,32+,36-,37-,38-,39+,40+,42-/m0/s1",ZPYMAPRFVXDPFZ-DNLKICPHSA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8-(4-methoxyphenethyl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684788,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,Stereochemistry assumed based on other MC congeners. Position of extra OCH2 on Hty not confirmed
CyanoMetDB_2049,MC‐Y(OMe)R,,,Microcystin,C53H74N10O14,1075.21,1074.538597,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=C(O)C(OC)=C3)=O)=O)=O)=O,"InChI=1S/C53H74N10O14/c1-28(24-29(2)41(76-8)26-34-14-11-10-12-15-34)17-19-36-30(3)45(66)60-38(51(72)73)20-22-43(65)63(7)33(6)48(69)57-32(5)47(68)61-39(25-35-18-21-40(64)42(27-35)77-9)50(71)62-44(52(74)75)31(4)46(67)59-37(49(70)58-36)16-13-23-56-53(54)55/h10-12,14-15,17-19,21,24,27,29-32,36-39,41,44,64H,6,13,16,20,22-23,25-26H2,1-5,7-9H3,(H,57,69)(H,58,70)(H,59,67)(H,60,66)(H,61,68)(H,62,71)(H,72,73)(H,74,75)(H4,54,55,56)/b19-17+,28-24+/t29-,30-,31-,32+,36-,37-,38+,39-,41-,44+/m0/s1",QKOFRVHIRGJZFD-IQEZPTFASA-N,"10-(3-((diaminomethylene)amino)propyl)-3-(4-hydroxybenzyl)-13-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-7,14,21,25-tetramethyl-22-methylene-4,8,11,15,20,23,26-heptaoxo-1-oxa-2,5,9,12,16,21,24-heptaazacycloheptacosane-6,17-dicarboxylic acid",155802286,,10.1071/MF13153,http://www.publish.csiro.au/?paper=MF13153,"Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa;Marine and Freshwater Research;65;2;;2014;journalArticle;10.1071/MF13153;Ballot, Andreas; Sandvik, Morten; Rundberget, Thomas; Botha, Christo J.; Miles, Christopher O.",Microcystis,aeruginosa,AB2011/53 and AQUAMEB-24,,MS2 available in the article. Position of extra OCH2 on Tyr not confirmed.
CyanoMetDB_2050,[seco‐4/5]MC‐HtyR,,,Microcystin,C53H76N10O14,1077.23,1076.554247,N[C@@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)[C@H](C)C(N[C@@H](C(O)=O)CCC(N(C)C(C(N[C@H](C)C(N[C@@H](CCC2=CC=C(O)C=C2)C(N[C@@H](C(O)=O)[C@H](C)C(N[C@@H](CCCNC(N)=N)C(O)=O)=O)=O)=O)=O)=C)=O)=O,"InChI=1S/C53H76N10O14/c1-29(27-30(2)42(77-8)28-36-13-10-9-11-14-36)16-22-38(54)31(3)45(66)61-41(51(73)74)24-25-43(65)63(7)34(6)48(69)58-33(5)47(68)59-39(23-19-35-17-20-37(64)21-18-35)49(70)62-44(52(75)76)32(4)46(67)60-40(50(71)72)15-12-26-57-53(55)56/h9-11,13-14,16-18,20-22,27,30-33,38-42,44,64H,6,12,15,19,23-26,28,54H2,1-5,7-8H3,(H,58,69)(H,59,68)(H,60,67)(H,61,66)(H,62,70)(H,71,72)(H,73,74)(H,75,76)(H4,55,56,57)/b22-16+,29-27+/t30-,31-,32-,33+,38-,39-,40-,41+,42-,44+/m0/s1",WTVAONJAVUUYCZ-CWXGWYCISA-N,"(29E,31E)-1,28-diamino-34-benzyl-13-(4-hydroxyphenethyl)-1-imino-9,16,20,27,31,33-hexamethyl-19-methylene-8,12,15,18,21,26-hexaoxo-35-oxa-2,7,11,14,17,20,25-heptaazahexatriaconta-29,31-diene-6,10,24-tricarboxylic acid",146684789,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,MS2 available in the article
CyanoMetDB_2051,[ADMAdda5]MC‐(H4)YR,,,Microcystin,C53H76N10O14,1077.23,1076.554247,O=C(CC[C@@H](NC([C@H]([C@@H](NC([C@@H](NC([C@H]([C@@H](NC([C@H](C[C@]1([H])CC[C@@H](O)C=C1)N2)=O)C(O)=O)C)=O)CCCNC(N)=N)=O)/C=C/C(C)=C/[C@@H]([C@H](CC3=CC=CC=C3)OC(C)=O)C)C)=O)C(O)=O)N(C(C(N[C@H](C)C2=O)=O)=C)C,"InChI=1S/C53H76N10O14/c1-28(25-29(2)42(77-34(7)64)27-35-13-10-9-11-14-35)16-21-38-30(3)45(67)60-40(51(73)74)22-23-43(66)63(8)33(6)48(70)57-32(5)47(69)61-41(26-36-17-19-37(65)20-18-36)50(72)62-44(52(75)76)31(4)46(68)59-39(49(71)58-38)15-12-24-56-53(54)55/h9-11,13-14,16-17,19,21,25,29-32,36-42,44,65H,6,12,15,18,20,22-24,26-27H2,1-5,7-8H3,(H,57,70)(H,58,71)(H,59,68)(H,60,67)(H,61,69)(H,62,72)(H,73,74)(H,75,76)(H4,54,55,56)/b21-16+,28-25+/t29-,30-,31-,32+,36-,37-,38-,39-,40+,41-,42-,44+/m0/s1",QHOIFLBUBXSKFD-CVMCXGGVSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684742,,10.1094/MPMI-22-6-0695,http://apsjournals.apsnet.org/doi/10.1094/MPMI-22-6-0695,"Microcystin Production in the Tripartite Cyanolichen Peltigera leucophlebia;Molecular Plant-Microbe Interactions;22;6;;2009;journalArticle;10.1094/MPMI-22-6-0695;Kaasalainen, Ulla; Jokela, Jouni; Fewer, David P.; Sivonen, Kaarina; Rikkinen, Jouko",Nostoc,sp.,[Nostoc sp.]UK18,,Stereochemistry inferred based on other MC congeners.
CyanoMetDB_2052,[Mser7]MC‐HtyR,,,Microcystin,C53H76N10O14,1077.23,1076.554247,O=C(N(C)[C@@H](CO)C(N[C@H](C)C1=O)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C53H76N10O14/c1-29(26-30(2)42(77-7)27-35-12-9-8-10-13-35)15-21-37-31(3)45(67)61-40(51(73)74)23-24-43(66)63(6)41(28-64)50(72)57-33(5)47(69)60-39(22-18-34-16-19-36(65)20-17-34)49(71)62-44(52(75)76)32(4)46(68)59-38(48(70)58-37)14-11-25-56-53(54)55/h8-10,12-13,15-17,19-21,26,30-33,37-42,44,64-65H,11,14,18,22-25,27-28H2,1-7H3,(H,57,72)(H,58,70)(H,59,68)(H,60,69)(H,61,67)(H,62,71)(H,73,74)(H,75,76)(H4,54,55,56)/b21-15+,29-26+/t30-,31-,32-,33+,37-,38-,39-,40+,41-,42-,44+/m0/s1",NIQDHGDEFXYGRF-AHSSRTABSA-N,"15-(3-((diaminomethylene)amino)propyl)-2-(hydroxymethyl)-8-(4-hydroxyphenethyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684790,,10.1021/es5029102,https://pubs.acs.org/doi/10.1021/es5029102,"Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656;Environmental Science & Technology;48;22;;2014;journalArticle;10.1021/es5029102;Miles, Christopher O.; Melanson, Jeremy E.; Ballot, Andreas",Anabaena/Dolichospermum,flos aquae,NIVA-CYA 656,,MS2 available in the article
CyanoMetDB_2053,"[D-Leu1,ADMAdda5]MC‐LHar",,,Microcystin,C54H82N10O13,1079.29,1078.606283,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C54H82N10O13/c1-29(2)25-41-50(71)62-42(26-30(3)4)51(72)63-45(53(75)76)34(8)47(68)59-39(19-15-16-24-57-54(55)56)49(70)58-38(21-20-31(5)27-32(6)43(77-36(10)65)28-37-17-13-12-14-18-37)33(7)46(67)60-40(52(73)74)22-23-44(66)64(11)35(9)48(69)61-41/h12-14,17-18,20-21,27,29-30,32-34,38-43,45H,9,15-16,19,22-26,28H2,1-8,10-11H3,(H,58,70)(H,59,68)(H,60,67)(H,61,69)(H,62,71)(H,63,72)(H,73,74)(H,75,76)(H4,55,56,57)/b21-20+,31-27+/t32-,33-,34-,38-,39-,40+,41+,42-,43-,45+/m0/s1",GZTFDRHWSWDGLX-COJYQKBUSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-5,8-diisobutyl-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802078,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,Stereochemistry inferred from other MC congeners. Bioaccumulated in lichen. Identified in Peltigera sp. (lichen species)
CyanoMetDB_2054,[ADMAdda5]MC‐RHar,,,Microcystin,C51H77N13O13,1080.24,1079.57638,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C51H77N13O13/c1-27(25-28(2)39(77-33(7)65)26-34-15-10-9-11-16-34)19-20-35-29(3)42(67)62-38(48(73)74)21-22-40(66)64(8)32(6)45(70)58-31(5)44(69)61-37(18-14-24-57-51(54)55)47(72)63-41(49(75)76)30(4)43(68)60-36(46(71)59-35)17-12-13-23-56-50(52)53/h9-11,15-16,19-20,25,28-31,35-39,41H,6,12-14,17-18,21-24,26H2,1-5,7-8H3,(H,58,70)(H,59,71)(H,60,68)(H,61,69)(H,62,67)(H,63,72)(H,73,74)(H,75,76)(H4,52,53,56)(H4,54,55,57)/b20-19+,27-25+/t28-,29-,30-,31+,35-,36-,37-,38+,39-,41+/m0/s1",AJYXDJVURKMIBH-DBOZVMTDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-8-(3-guanidinopropyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801629,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,Stereochemistry inferred from other MC congeners. Bioaccumulated in lichen. Identified in Nephroma parile (lichen species)
CyanoMetDB_2055,[D-Leu1]MC-RR,,,Microcystin,C52H81N13O12,1080.28,1079.612765,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C52H81N13O12/c1-28(2)25-39-48(72)61-37(18-14-24-58-52(55)56)47(71)64-42(50(75)76)32(6)44(68)60-36(17-13-23-57-51(53)54)46(70)59-35(20-19-29(3)26-30(4)40(77-9)27-34-15-11-10-12-16-34)31(5)43(67)62-38(49(73)74)21-22-41(66)65(8)33(7)45(69)63-39/h10-12,15-16,19-20,26,28,30-32,35-40,42H,7,13-14,17-18,21-25,27H2,1-6,8-9H3,(H,59,70)(H,60,68)(H,61,72)(H,62,67)(H,63,69)(H,64,71)(H,73,74)(H,75,76)(H4,53,54,57)(H4,55,56,58)/b20-19+,29-26+/t30-,31-,32-,35-,36-,37-,38+,39+,40-,42+/m0/s1",BMULUGRVOLWIKI-AHYMVQLDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684772,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Phormidium,sp.,[Phormidium sp.]CENA270,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_2056,MC‐OiaR,MC‐OiaR (oxidised W),,Microcystin,C54H73N11O13,1084.22,1083.538932,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3C(C=CC=C4)=C4NC3=O)=O)=O)=O)=O,"InChI=1S/C54H73N11O13/c1-28(25-29(2)42(78-8)26-34-15-10-9-11-16-34)20-21-37-30(3)45(67)62-40(52(74)75)22-23-43(66)65(7)33(6)48(70)58-32(5)47(69)63-41(27-36-35-17-12-13-18-38(35)60-49(36)71)51(73)64-44(53(76)77)31(4)46(68)61-39(50(72)59-37)19-14-24-57-54(55)56/h9-13,15-18,20-21,25,29-32,36-37,39-42,44H,6,14,19,22-24,26-27H2,1-5,7-8H3,(H,58,70)(H,59,72)(H,60,71)(H,61,68)(H,62,67)(H,63,69)(H,64,73)(H,74,75)(H,76,77)(H4,55,56,57)/b21-20+,28-25+/t29-,30-,31-,32+,36?,37-,39-,40+,41-,42-,44+/m0/s1",RTWKALOUNJLWMT-JFXBHVICSA-N,"15-(3-((diaminomethylene)amino)propyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-((2-oxoindolin-3-yl)methyl)-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683828,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,," MS/MS with Bruker AmaZon X ESI MS, HRMS with Bruker MicrOTOF MS"
CyanoMetDB_2057,"[D-Met(O)1,D-MeO-Glu6]MC‐LR","[D-Met(O)1,Glu(OMe)6]MC‐LR",,Microcystin,C52H80N10O13S,1085.32,1084.562704,O=C(N(C)C(C(N[C@@H](C1=O)CCS(C)=O)=O)=C)CC[C@H](C(OC)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C52H80N10O13S/c1-29(2)26-40-49(69)61-43(50(70)71)33(6)45(65)57-37(18-15-24-55-52(53)54)47(67)56-36(20-19-30(3)27-31(4)41(74-9)28-35-16-13-12-14-17-35)32(5)44(64)59-39(51(72)75-10)21-22-42(63)62(8)34(7)46(66)58-38(48(68)60-40)23-25-76(11)73/h12-14,16-17,19-20,27,29,31-33,36-41,43H,7,15,18,21-26,28H2,1-6,8-11H3,(H,56,67)(H,57,65)(H,58,66)(H,59,64)(H,60,68)(H,61,69)(H,70,71)(H4,53,54,55)/b20-19+,30-27+/t31-,32-,33-,36-,37-,38+,39+,40-,41-,43+,76?/m0/s1",RHTINHKLEAGZRI-MPCZMROASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-22-(methoxycarbonyl)-1,12,19-trimethyl-2-methylene-5-(2-(methylsulfinyl)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11-carboxylic acid",146683875,,10.1002/rcm.7098,http://doi.wiley.com/10.1002/rcm.7098,"Seven new microcystin variants discovered from a native Microcystis aeruginosa strain - unambiguous assignment of product ions by tandem mass spectrometry: Discovery of microcystins by MS/MS;Rapid Communications in Mass Spectrometry;29;2;;2015;journalArticle;10.1002/rcm.7098;Qi, Yulin; Rosso, Lorena; Sedan, Daniela; Giannuzzi, Leda; Andrinolo, Dario; Volmer, Dietrich A.",Microcystis,aeruginosa,[Microcystis aeruginosa] CAAT 2005-3,,Stereochemistry assumed based on other MC congeners (identification by MS only). Also detected in Peltigera degenii (lichen species)
CyanoMetDB_2058,[D-Leu1]MC-HphR,,,Microcystin,C56H80N10O12,1085.29,1084.595718,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C56H80N10O12/c1-32(2)29-44-53(73)62-42(25-23-38-17-12-10-13-18-38)52(72)65-47(55(76)77)36(6)49(69)61-41(21-16-28-59-56(57)58)51(71)60-40(24-22-33(3)30-34(4)45(78-9)31-39-19-14-11-15-20-39)35(5)48(68)63-43(54(74)75)26-27-46(67)66(8)37(7)50(70)64-44/h10-15,17-20,22,24,30,32,34-36,40-45,47H,7,16,21,23,25-29,31H2,1-6,8-9H3,(H,60,71)(H,61,69)(H,62,73)(H,63,68)(H,64,70)(H,65,72)(H,74,75)(H,76,77)(H4,57,58,59)/b24-22+,33-30+/t34-,35-,36-,40-,41-,42-,43+,44+,45-,47+/m0/s1",ZDUORUGJYRAXQK-AWTKRBTQSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-8-phenethyl-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684773,,10.1186/1471-2148-13-86,http://bmcevolbiol.biomedcentral.com/articles/10.1186/1471-2148-13-86,"Convergent evolution of [D-Leucine1] microcystin-LR in taxonomically disparate cyanobacteria;BMC Evolutionary Biology;13;1;;2013;journalArticle;10.1186/1471-2148-13-86;Shishido, Tânia; Kaasalainen, Ulla; Fewer, David P; Rouhiainen, Leo; Jokela, Jouni; Wahlsten, Matti; Fiore, Marli; Yunes, João; Rikkinen, Jouko; Sivonen, Kaarina",Microcystis,sp.,RST9501,,"Identification primarily by LC-MS/MS with stereochemical analysis of alanine, leucine, arginine and homoargenine residues. Remainder of stereochemistry assumed based on other MC congeners."
CyanoMetDB_2059,[D-Leu1]MC-M(O2)R,,,Microcystin,C51H78N10O14S,1087.3,1086.54197,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCS(C)(=O)=O)=O)=O)=O)=O,"InChI=1S/C51H78N10O14S/c1-28(2)25-39-48(68)57-37(22-24-76(10,73)74)47(67)60-42(50(71)72)32(6)44(64)56-36(17-14-23-54-51(52)53)46(66)55-35(19-18-29(3)26-30(4)40(75-9)27-34-15-12-11-13-16-34)31(5)43(63)58-38(49(69)70)20-21-41(62)61(8)33(7)45(65)59-39/h11-13,15-16,18-19,26,28,30-32,35-40,42H,7,14,17,20-25,27H2,1-6,8-10H3,(H,55,66)(H,56,64)(H,57,68)(H,58,63)(H,59,65)(H,60,67)(H,69,70)(H,71,72)(H4,52,53,54)/b19-18+,29-26+/t30-,31-,32-,35-,36-,37-,38+,39+,40-,42+/m0/s1",PSBIEJGKICVXRC-OIGYFXLDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-8-(2-(methylsulfonyl)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802273,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ",Seen as autoxidation artefact (synthetic)
CyanoMetDB_2060,[ADMAdda5]MC‐(H4)YHar,,,Microcystin,C54H78N10O14,1091.26,1090.569898,O=C(CC[C@@H](NC([C@H]([C@@H](NC([C@@H](NC([C@H]([C@@H](NC([C@H](C[C@]1([H])CC[C@@H](O)C=C1)N2)=O)C(O)=O)C)=O)CCCCNC(N)=N)=O)/C=C/C(C)=C/[C@@H]([C@H](CC3=CC=CC=C3)OC(C)=O)C)C)=O)C(O)=O)N(C(C(N[C@H](C)C2=O)=O)=C)C,"InChI=1S/C54H78N10O14/c1-29(26-30(2)43(78-35(7)65)28-36-14-10-9-11-15-36)17-22-39-31(3)46(68)61-41(52(74)75)23-24-44(67)64(8)34(6)49(71)58-33(5)48(70)62-42(27-37-18-20-38(66)21-19-37)51(73)63-45(53(76)77)32(4)47(69)60-40(50(72)59-39)16-12-13-25-57-54(55)56/h9-11,14-15,17-18,20,22,26,30-33,37-43,45,66H,6,12-13,16,19,21,23-25,27-28H2,1-5,7-8H3,(H,58,71)(H,59,72)(H,60,69)(H,61,68)(H,62,70)(H,63,73)(H,74,75)(H,76,77)(H4,55,56,57)/b22-17+,29-26+/t30-,31-,32-,33+,37-,38-,39-,40-,41+,42-,43-,45+/m0/s1",OCQCDEXNHUNYCY-BPLSHEKDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-15-(4-guanidinobutyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684743,,10.1094/MPMI-22-6-0695,http://apsjournals.apsnet.org/doi/10.1094/MPMI-22-6-0695,"Microcystin Production in the Tripartite Cyanolichen Peltigera leucophlebia;Molecular Plant-Microbe Interactions;22;6;;2009;journalArticle;10.1094/MPMI-22-6-0695;Kaasalainen, Ulla; Jokela, Jouni; Fewer, David P.; Sivonen, Kaarina; Rikkinen, Jouko",Nostoc,sp.,[Nostoc sp.]UK18,,Stereochemistry inferred based on other MC congeners.
CyanoMetDB_2061,MC‐NfkR,MC‐NfkR (oxidised W),,Microcystin,C54H73N11O14,1100.22,1099.533846,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C(C=CC=C3)=C3NC=O)=O)=O)=O)=O)=O,"InChI=1S/C54H73N11O14/c1-29(25-30(2)43(79-8)26-35-15-10-9-11-16-35)20-21-37-31(3)46(69)62-40(52(75)76)22-23-44(68)65(7)34(6)49(72)59-33(5)48(71)63-41(27-42(67)36-17-12-13-18-38(36)58-28-66)51(74)64-45(53(77)78)32(4)47(70)61-39(50(73)60-37)19-14-24-57-54(55)56/h9-13,15-18,20-21,25,28,30-33,37,39-41,43,45H,6,14,19,22-24,26-27H2,1-5,7-8H3,(H,58,66)(H,59,72)(H,60,73)(H,61,70)(H,62,69)(H,63,71)(H,64,74)(H,75,76)(H,77,78)(H4,55,56,57)/b21-20+,29-25+/t30-,31-,32-,33+,37-,39-,40+,41-,43-,45+/m0/s1",SFEHDORCXZBIOU-CFJCUTGNSA-N,"15-(3-((diaminomethylene)amino)propyl)-8-(2-(2-formamidophenyl)-2-oxoethyl)-18-((1E,3E)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683829,,10.3390/md11083025,http://www.mdpi.com/1660-3397/11/8/3025,"Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues;Marine Drugs;11;8;;2013;journalArticle;10.3390/md11083025;Puddick, Jonathan; Prinsep, Michèle; Wood, Susanna; Miles, Christopher; Rise, Frode; Cary, Stephen; Hamilton, David; Wilkins, Alistair",Microcystis,sp.,[Microcystis sp.]CAWBG11,," MS/MS with Bruker AmaZon X ESI MS, HRMS with Bruker MicrOTOF MS"
CyanoMetDB_2062,[D-Leu1]MC‐HtyR,,,Microcystin,C56H80N10O13,1101.29,1100.590633,O=C(N(C)C(C(N[C@@H](C1=O)CC(C)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C56H80N10O13/c1-31(2)28-44-53(74)62-42(24-20-37-18-21-39(67)22-19-37)52(73)65-47(55(77)78)35(6)49(70)61-41(16-13-27-59-56(57)58)51(72)60-40(23-17-32(3)29-33(4)45(79-9)30-38-14-11-10-12-15-38)34(5)48(69)63-43(54(75)76)25-26-46(68)66(8)36(7)50(71)64-44/h10-12,14-15,17-19,21-23,29,31,33-35,40-45,47,67H,7,13,16,20,24-28,30H2,1-6,8-9H3,(H,60,72)(H,61,70)(H,62,74)(H,63,69)(H,64,71)(H,65,73)(H,75,76)(H,77,78)(H4,57,58,59)/b23-17+,32-29+/t33-,34-,35-,40-,41-,42-,43+,44+,45-,47+/m0/s1",NIUNWCDFPXGJEK-QXTGSMIGSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(4-hydroxyphenethyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802223,,10.1073/pnas.1200279109,http://www.pnas.org/cgi/doi/10.1073/pnas.1200279109,"Cyanobacteria produce a high variety of hepatotoxic peptides in lichen symbiosis;Proceedings of the National Academy of Sciences;109;15;;2012;journalArticle;10.1073/pnas.1200279109;Kaasalainen, U.; Fewer, D. P.; Jokela, J.; Wahlsten, M.; Sivonen, K.; Rikkinen, J.",n.a.,n.a.,n.a.,,"Stereochemistry assumed based on other MC congeners. Bioaccumulated in lichen. Identified in Peltigera membranacea, Peltigera degenii, Nostoc sp. strain 89.II, Peltigera membranacea, Nostoc sp. strain 92.II and Peltigera degenii. Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_2063,"[D-Leu1,Ser7]MC-HtyR","[D-Leu1,L-Ser7]MC-HtyR",,Microcystin,C55H80N10O14,1105.28,1104.585547,O=C(N[C@@H](CO)C(N[C@@H](C1=O)CC(C)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C55H80N10O14/c1-30(2)26-42-51(73)62-40(22-18-35-16-19-37(67)20-17-35)50(72)65-46(54(77)78)34(6)48(70)61-39(14-11-25-58-55(56)57)49(71)60-38(21-15-31(3)27-32(4)44(79-7)28-36-12-9-8-10-13-36)33(5)47(69)63-41(53(75)76)23-24-45(68)59-43(29-66)52(74)64-42/h8-10,12-13,15-17,19-21,27,30,32-34,38-44,46,66-67H,11,14,18,22-26,28-29H2,1-7H3,(H,59,68)(H,60,71)(H,61,70)(H,62,73)(H,63,69)(H,64,74)(H,65,72)(H,75,76)(H,77,78)(H4,56,57,58)/b21-15+,31-27+/t32-,33-,34-,38-,39-,40-,41+,42+,43-,44-,46+/m0/s1",LPFSGSMIIHIZHU-HRPRKDRMSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-2-(hydroxymethyl)-8-(4-hydroxyphenethyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-12,19-dimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146683808,,10.3390/toxins11110619,https://www.mdpi.com/2072-6651/11/11/619,"A Data-Independent Methodology for the Structural Characterization of Microcystins and Anabaenopeptins Leading to the Identification of Four New Congeners;Toxins;11;11;;2019;journalArticle;10.3390/toxins11110619;Roy-Lachapelle, Audrey; Solliec, Morgan; Sauvé, Sébastien; Gagnon, Christian",n.a.,n.a.,n.a.,"field samples, blooms located in Canada, United Kingdom and France",
CyanoMetDB_2064,[Mdha-Cys7]MC-LR,"[L‐MeLan7]MC‐LR, MC-LR-Cys",,Microcystin,C52H81N11O14S,1116.33,1115.568517,O=C(N(C1([H])CSC[C@@H](C(O)=O)N)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C52H81N11O14S/c1-27(2)22-38-47(69)62-42(51(75)76)31(6)44(66)59-36(16-13-21-56-52(54)55)46(68)58-35(18-17-28(3)23-29(4)40(77-9)24-33-14-11-10-12-15-33)30(5)43(65)60-37(50(73)74)19-20-41(64)63(8)39(26-78-25-34(53)49(71)72)48(70)57-32(7)45(67)61-38/h10-12,14-15,17-18,23,27,29-32,34-40,42H,13,16,19-22,24-26,53H2,1-9H3,(H,57,70)(H,58,68)(H,59,66)(H,60,65)(H,61,67)(H,62,69)(H,71,72)(H,73,74)(H,75,76)(H4,54,55,56)/b18-17+,28-23+/t29-,30-,31-,32+,34-,35-,36-,37+,38-,39?,40-,42+/m0/s1",VXYRNKOTKQZSDD-SZEQAKQOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-amino-2-carboxyethyl)thio)methyl)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802384,,10.1021/tx00029a002,https://pubs.acs.org/doi/abs/10.1021/tx00029a002,"Formation, characterization, and toxicity of the glutathione and cysteine conjugates of toxic heptapeptide microcystins;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a002;Kondo, Fumio; Ikai, Yoshitomo; Oka, Hisao; Okumura, Masanao; Ishikawa, Naohisa; Harada, Kenichi; Matsuura, Kenji; Murata, Hideaki; Suzuki, Makoto",n.a.,n.a.,n.a.,"Parent compound derived from field sample, surface bloom collected from Lake Suwa, Japan","Semisynthetic. Kondo et al. prepared this compound synthetically, but anticipated in biological samples. Stereochemistry at Mdha-Cys undefined in cited literature. All other stereochemical centers assumed based on other MC congeners."
CyanoMetDB_2065,"[D-Leu1,Mdha-Cys7]MC-LR",,,Microcystin,C55H87N11O14S,1158.41,1157.61547,O=C(N(C1([H])CSC[C@@H](C(O)=O)N)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](CC(C)C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C55H87N11O14S/c1-29(2)23-40-49(71)63-41(24-30(3)4)50(72)65-45(54(78)79)34(8)47(69)61-38(17-14-22-59-55(57)58)48(70)60-37(19-18-31(5)25-32(6)43(80-10)26-35-15-12-11-13-16-35)33(7)46(68)62-39(53(76)77)20-21-44(67)66(9)42(51(73)64-40)28-81-27-36(56)52(74)75/h11-13,15-16,18-19,25,29-30,32-34,36-43,45H,14,17,20-24,26-28,56H2,1-10H3,(H,60,70)(H,61,69)(H,62,68)(H,63,71)(H,64,73)(H,65,72)(H,74,75)(H,76,77)(H,78,79)(H4,57,58,59)/b19-18+,31-25+/t32-,33-,34-,36-,37-,38-,39+,40+,41-,42?,43-,45+/m0/s1",CMGBBWNITZBJCW-QRELNUNZSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-amino-2-carboxyethyl)thio)methyl)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802015,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Confirmed by semi-synthesis from [Leu1]MC-LR, not thiol reactive, oxidised by H2O2"
CyanoMetDB_2066,MC‐RY,,,Microcystin,C52H72N10O13,1045.19,1044.528033,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C52H72N10O13/c1-28(25-29(2)41(75-8)27-34-13-10-9-11-14-34)16-21-37-30(3)44(65)59-39(50(71)72)22-23-42(64)62(7)33(6)47(68)56-32(5)46(67)58-38(15-12-24-55-52(53)54)48(69)61-43(51(73)74)31(4)45(66)60-40(49(70)57-37)26-35-17-19-36(63)20-18-35/h9-11,13-14,16-21,25,29-32,37-41,43,63H,6,12,15,22-24,26-27H2,1-5,7-8H3,(H,56,68)(H,57,70)(H,58,67)(H,59,65)(H,60,66)(H,61,69)(H,71,72)(H,73,74)(H4,53,54,55)/b21-16+,28-25+/t29-,30-,31-,32+,37-,38-,39+,40-,41-,43+/m0/s1",YCVNLMLOLNNEKI-GJRPNUFSSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(3-guanidinopropyl)-15-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",139597972,,10.1002/tox.20522,http://doi.wiley.com/10.1002/tox.20522,"Occurrence of microcystin-producing cyanobacteria in Ugandan freshwater habitats;Environmental Toxicology;25;4;;2009;journalArticle;10.1002/tox.20522;Okello, William; Portmann, Cyril; Erhard, Marcel; Gademann, Karl; Kurmayer, Rainer",n.a.,n.a.,n.a.,"field sample, Microcystis bloom","Stereochemistry well defined by NMR. Detected in microcystin-containing cyanobacterial bloom samples (20 L) from Mwanza Gulf in Lake Victoria, Tanzania, in 2010. MS2 available in the article"
CyanoMetDB_2067,[Mdha-Cys7]MC-YR,,,Microcystin,C55H79N11O15S,1166.35,1165.547782,O=C(N(C1([H])CSC[C@@H](C(O)=O)N)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C55H79N11O15S/c1-29(24-30(2)43(81-7)26-34-12-9-8-10-13-34)15-20-38-31(3)46(69)63-40(53(77)78)21-22-44(68)66(6)42(28-82-27-37(56)52(75)76)51(74)60-33(5)48(71)64-41(25-35-16-18-36(67)19-17-35)50(73)65-45(54(79)80)32(4)47(70)62-39(49(72)61-38)14-11-23-59-55(57)58/h8-10,12-13,15-20,24,30-33,37-43,45,67H,11,14,21-23,25-28,56H2,1-7H3,(H,60,74)(H,61,72)(H,62,70)(H,63,69)(H,64,71)(H,65,73)(H,75,76)(H,77,78)(H,79,80)(H4,57,58,59)/b20-15+,29-24+/t30-,31-,32-,33+,37-,38-,39-,40+,41-,42?,43-,45+/m0/s1",GCAHWPNUAYNFOD-PJRXKZDCSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-amino-2-carboxyethyl)thio)methyl)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802058,,10.1021/tx00029a002,https://pubs.acs.org/doi/abs/10.1021/tx00029a002,"Formation, characterization, and toxicity of the glutathione and cysteine conjugates of toxic heptapeptide microcystins;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a002;Kondo, Fumio; Ikai, Yoshitomo; Oka, Hisao; Okumura, Masanao; Ishikawa, Naohisa; Harada, Kenichi; Matsuura, Kenji; Murata, Hideaki; Suzuki, Makoto",n.a.,n.a.,n.a.,"field sample, surface bloom collected from Lake Suwa, Japan","Semisynthetic Kondo et al. formed this compound chemically. Nevertheless, anticipated in organisms."
CyanoMetDB_2068,"[D-Leu1,Mdha-Cys(O)7]MC-LR",,,Microcystin,C55H87N11O15S,1174.41,1173.61038,O=C(N(C1([H])CS(C[C@@H](C(O)=O)N)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](CC(C)C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C55H87N11O15S/c1-29(2)23-40-49(71)63-41(24-30(3)4)50(72)65-45(54(78)79)34(8)47(69)61-38(17-14-22-59-55(57)58)48(70)60-37(19-18-31(5)25-32(6)43(81-10)26-35-15-12-11-13-16-35)33(7)46(68)62-39(53(76)77)20-21-44(67)66(9)42(51(73)64-40)28-82(80)27-36(56)52(74)75/h11-13,15-16,18-19,25,29-30,32-34,36-43,45H,14,17,20-24,26-28,56H2,1-10H3,(H,60,70)(H,61,69)(H,62,68)(H,63,71)(H,64,73)(H,65,72)(H,74,75)(H,76,77)(H,78,79)(H4,57,58,59)/b19-18+,31-25+/t32-,33-,34-,36-,37-,38-,39+,40+,41-,42?,43-,45+,82?/m0/s1",MTXIGOBZSPZTQX-CMHNIRSYSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-amino-2-carboxyethyl)sulfinyl)methyl)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802200,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Confirmed by semi-synthesis from [Leu1]MC-LR, not thiol reactive"
CyanoMetDB_2069,[Mdha-NAcCys7]MC-RR,,,Microcystin,C54H84N14O15S,1201.39,1200.596129,O=C(N(C1([H])CSC[C@@H](C(O)=O)NC(C)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C54H84N14O15S/c1-28(24-29(2)41(83-8)25-34-14-10-9-11-15-34)18-19-35-30(3)44(71)66-38(50(77)78)20-21-42(70)68(7)40(27-84-26-39(51(79)80)62-33(6)69)49(76)61-32(5)46(73)65-37(17-13-23-60-54(57)58)48(75)67-43(52(81)82)31(4)45(72)64-36(47(74)63-35)16-12-22-59-53(55)56/h9-11,14-15,18-19,24,29-32,35-41,43H,12-13,16-17,20-23,25-27H2,1-8H3,(H,61,76)(H,62,69)(H,63,74)(H,64,72)(H,65,73)(H,66,71)(H,67,75)(H,77,78)(H,79,80)(H,81,82)(H4,55,56,59)(H4,57,58,60)/b19-18+,28-24+/t29-,30-,31-,32+,35-,36-,37-,38+,39-,40?,41-,43+/m0/s1",DNHZIEKBSAAFQR-KRMQMZFJSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-acetamido-2-carboxyethyl)thio)methyl)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802034,,10.1016/j.aquatox.2013.12.001,https://linkinghub.elsevier.com/retrieve/pii/S0166445X13003408,"Rapid conversion and reversible conjugation of glutathione detoxification of microcystins in bighead carp (Aristichthys nobilis);Aquatic Toxicology;147;;;2014;journalArticle;10.1016/j.aquatox.2013.12.001;Li, Wei; Chen, Jun; Xie, Ping; He, Jun; Guo, Xiaochun; Tuo, Xun; Zhang, Wei; Wu, Laiyan",n.a.,n.a.,n.a.,,"Bioaccumulated in bighead carp (Aristichthys nobilis). Semisynthesis, LC-MS."
CyanoMetDB_2070,"[D-Leu1,Mdha-GluCys7]MC-LR",,,Microcystin,C60H94N12O17S,1287.52,1286.65806,O=C(N(C1([H])CSC[C@@H](C(O)=O)NC(CC[C@H](N)C(O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](CC(C)C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C60H94N12O17S/c1-31(2)25-42-53(78)69-43(26-32(3)4)54(79)71-49(59(87)88)36(8)51(76)67-40(17-14-24-64-60(62)63)52(77)66-39(20-18-33(5)27-34(6)46(89-10)28-37-15-12-11-13-16-37)35(7)50(75)68-41(57(83)84)21-23-48(74)72(9)45(55(80)70-42)30-90-29-44(58(85)86)65-47(73)22-19-38(61)56(81)82/h11-13,15-16,18,20,27,31-32,34-36,38-46,49H,14,17,19,21-26,28-30,61H2,1-10H3,(H,65,73)(H,66,77)(H,67,76)(H,68,75)(H,69,78)(H,70,80)(H,71,79)(H,81,82)(H,83,84)(H,85,86)(H,87,88)(H4,62,63,64)/b20-18+,33-27+/t34-,35-,36-,38-,39-,40-,41+,42+,43-,44-,45?,46-,49+/m0/s1",WRJSBJQBDKYVCM-STYWWRLESA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-2-carboxyethyl)thio)methyl)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802401,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Confirmed by semi-synthesis from [Leu1]MC-LR, not thiol reactive"
CyanoMetDB_2071,[Mdha-GSH7]MC-LR,MC-LR-GSH,,Microcystin,C59H91N13O18S,1302.5,1301.632574,O=C(N(C1([H])CSC[C@@H](C(NCC(O)=O)=O)NC(CC[C@H](N)C(O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C59H91N13O18S/c1-30(2)24-41-54(82)71-48(58(88)89)34(6)50(78)68-39(16-13-23-63-59(61)62)53(81)67-38(19-17-31(3)25-32(4)44(90-9)26-36-14-11-10-12-15-36)33(5)49(77)69-40(57(86)87)20-22-46(74)72(8)43(55(83)65-35(7)51(79)70-41)29-91-28-42(52(80)64-27-47(75)76)66-45(73)21-18-37(60)56(84)85/h10-12,14-15,17,19,25,30,32-35,37-44,48H,13,16,18,20-24,26-29,60H2,1-9H3,(H,64,80)(H,65,83)(H,66,73)(H,67,81)(H,68,78)(H,69,77)(H,70,79)(H,71,82)(H,75,76)(H,84,85)(H,86,87)(H,88,89)(H4,61,62,63)/b19-17+,31-25+/t32-,33-,34-,35+,37-,38-,39-,40+,41-,42-,43?,44-,48+/m0/s1",VLOIKSDQZCUMEK-XUMORHROSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-3-((carboxymethyl)amino)-3-oxopropyl)thio)methyl)-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802378,,10.1021/tx00029a002,https://pubs.acs.org/doi/abs/10.1021/tx00029a002,"Formation, characterization, and toxicity of the glutathione and cysteine conjugates of toxic heptapeptide microcystins;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a002;Kondo, Fumio; Ikai, Yoshitomo; Oka, Hisao; Okumura, Masanao; Ishikawa, Naohisa; Harada, Kenichi; Matsuura, Kenji; Murata, Hideaki; Suzuki, Makoto",n.a.,n.a.,n.a.,,Semisynthetic. Original paper by Kondo et al. demonstrated the chemical formation of this compound. Multiple subsequent papers have detected these conjugates in biological extracts.
CyanoMetDB_2072,"[D-Leu1,Mdha-GluCys(O)7]MC-LR",,,Microcystin,C60H94N12O18S,1303.52,1302.65297,O=C(N(C1([H])CS(C[C@@H](C(O)=O)NC(CC[C@H](N)C(O)=O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](CC(C)C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C60H94N12O18S/c1-31(2)25-42-53(78)69-43(26-32(3)4)54(79)71-49(59(87)88)36(8)51(76)67-40(17-14-24-64-60(62)63)52(77)66-39(20-18-33(5)27-34(6)46(90-10)28-37-15-12-11-13-16-37)35(7)50(75)68-41(57(83)84)21-23-48(74)72(9)45(55(80)70-42)30-91(89)29-44(58(85)86)65-47(73)22-19-38(61)56(81)82/h11-13,15-16,18,20,27,31-32,34-36,38-46,49H,14,17,19,21-26,28-30,61H2,1-10H3,(H,65,73)(H,66,77)(H,67,76)(H,68,75)(H,69,78)(H,70,80)(H,71,79)(H,81,82)(H,83,84)(H,85,86)(H,87,88)(H4,62,63,64)/b20-18+,33-27+/t34-,35-,36-,38-,39-,40-,41+,42+,43-,44-,45?,46-,49+,91?/m0/s1",KMKFAGRMGIMMRM-ZJDQKBGBSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-2-carboxyethyl)sulfinyl)methyl)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802162,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Confirmed by semi-synthesis from [Leu1]MC-LR, not thiol reactive"
CyanoMetDB_2073,"[D-Asp3,Mdha-GSH7]MC-RR",[D-Asp3]MC-RR-GSH,,Microcystin,C58H90N16O18S,1331.5,1330.633971,O=C(N(C1([H])CSC[C@@H](C(NCC(O)=O)=O)NC(CC[C@H](N)C(O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC(C[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C58H90N16O18S/c1-30(24-31(2)43(92-6)25-34-12-8-7-9-13-34)16-18-36-32(3)48(80)72-39(55(88)89)19-21-46(77)74(5)42(29-93-28-41(50(82)66-27-47(78)79)69-44(75)20-17-35(59)54(86)87)53(85)67-33(4)49(81)71-38(15-11-23-65-58(62)63)52(84)73-40(56(90)91)26-45(76)68-37(51(83)70-36)14-10-22-64-57(60)61/h7-9,12-13,16,18,24,31-33,35-43H,10-11,14-15,17,19-23,25-29,59H2,1-6H3,(H,66,82)(H,67,85)(H,68,76)(H,69,75)(H,70,83)(H,71,81)(H,72,80)(H,73,84)(H,78,79)(H,86,87)(H,88,89)(H,90,91)(H4,60,61,64)(H4,62,63,65)/b18-16+,30-24+/t31-,32-,33+,35-,36-,37-,38-,39+,40+,41-,42?,43-/m0/s1",PXEOFGCLNPSOIR-AJXKSCHMSA-N,"(5R,8S,11R,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-3-((carboxymethyl)amino)-3-oxopropyl)thio)methyl)-8,15-bis(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684920,,10.3390/md17110643,https://www.mdpi.com/1660-3397/17/11/643,"Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling;Marine Drugs;17;11;;2019;journalArticle;10.3390/md17110643;Mallia, Vittoria; Uhlig, Silvio; Rafuse, Cheryl; Meija, Juris; Miles, Christopher O.",Planktothrix,prolifica,NIVA-CYA 544,,"Confirmed by semi-synthesis from [Asp3]MC-RR, not thiol reactive, LC-HRMS/MS"
CyanoMetDB_2074,"[D-Leu1,Mdha-GSH7]MC-LR",,,Microcystin,C62H97N13O18S,1344.57,1343.67952,O=C(N(C1([H])CSC[C@@H](C(NCC(O)=O)=O)NC(CC[C@H](N)C(O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](CC(C)C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C62H97N13O18S/c1-32(2)25-43-56(84)72-44(26-33(3)4)57(85)74-51(61(91)92)37(8)53(81)70-41(17-14-24-66-62(64)65)55(83)69-40(20-18-34(5)27-35(6)47(93-10)28-38-15-12-11-13-16-38)36(7)52(80)71-42(60(89)90)21-23-49(77)75(9)46(58(86)73-43)31-94-30-45(54(82)67-29-50(78)79)68-48(76)22-19-39(63)59(87)88/h11-13,15-16,18,20,27,32-33,35-37,39-47,51H,14,17,19,21-26,28-31,63H2,1-10H3,(H,67,82)(H,68,76)(H,69,83)(H,70,81)(H,71,80)(H,72,84)(H,73,86)(H,74,85)(H,78,79)(H,87,88)(H,89,90)(H,91,92)(H4,64,65,66)/b20-18+,34-27+/t35-,36-,37-,39-,40-,41-,42+,43+,44-,45-,46?,47-,51+/m0/s1",MVFPUYGZNZXUAN-HSROGDTGSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-3-((carboxymethyl)amino)-3-oxopropyl)thio)methyl)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802204,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Confirmed by semi-synthesis from [Leu1]MC-LR, not thiol reactive, oxidised by H2O2"
CyanoMetDB_2075,[ADMAdda5]MC‐RR,,,Microcystin,C50H75N13O13,1066.21,1065.5607,O=C(N(C)C(C(N[C@H](C)C1=O)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC(C)=O)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C50H75N13O13/c1-26(24-27(2)38(76-32(7)64)25-33-14-10-9-11-15-33)18-19-34-28(3)41(66)61-37(47(72)73)20-21-39(65)63(8)31(6)44(69)57-30(5)43(68)60-36(17-13-23-56-50(53)54)46(71)62-40(48(74)75)29(4)42(67)59-35(45(70)58-34)16-12-22-55-49(51)52/h9-11,14-15,18-19,24,27-30,34-38,40H,6,12-13,16-17,20-23,25H2,1-5,7-8H3,(H,57,69)(H,58,70)(H,59,67)(H,60,68)(H,61,66)(H,62,71)(H,72,73)(H,74,75)(H4,51,52,55)(H4,53,54,56)/b19-18+,26-24+/t27-,28-,29-,30+,34-,35-,36-,37+,38-,40+/m0/s1",XRUQQFIWAFYUJA-SXWZSMJNSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-acetoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-8,15-bis(3-guanidinopropyl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684855,,10.1002/rcm.4006,http://doi.wiley.com/10.1002/rcm.4006,"Liquid chromatography coupled to quadruple time-of-flight tandem mass spectrometry for microcystin analysis in freshwaters: method performances and characterisation of a novel variant of microcystin-RR;Rapid Communications in Mass Spectrometry;23;9;;2009;journalArticle;10.1002/rcm.4006;Ferranti, Pasquale; Fabbrocino, Serena; Nasi, Antonella; Caira, Simonetta; Bruno, Milena; Serpe, Luigi; Gallo, Pasquale",n.a.,n.a.,n.a.,"field sample: lake Averno, Italy, 2007, Planktothrix rubescens","Stereochemistry assumed based on other MC congeners. [Ferranti 2009] Detected in field sample of Planktothrix rubescens collected from Lake Averno, Italy, in March / June 2007; [Kaasalanien 2012] Bioaccumulated in lichen. Identified in Nephroma parile, Peltigera hymenina, Peltigera collina, Peltigera leucophlebia and Peltigera praetextata (liquen species). Extent of characterisation by LC-MS(/MS) is not explicitly defined in the article, with the compound mentioned only in SI materials."
CyanoMetDB_2076,[Mdha-GSH7]MC-YR,MC-YR-GSH,,Microcystin,C62H89N13O19S,1352.51,1351.611839,O=C(N(C1([H])CSC[C@@H](C(NCC(O)=O)=O)NC(CC[C@H](N)C(O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](C)NC1=O)=O)CC3=CC=C(O)C=C3)=O)=O)=O)=O,"InChI=1S/C62H89N13O19S/c1-32(26-33(2)47(94-7)28-37-12-9-8-10-13-37)15-21-41-34(3)52(81)72-43(60(90)91)22-24-49(78)75(6)46(31-95-30-45(55(84)67-29-50(79)80)69-48(77)23-20-40(63)59(88)89)58(87)68-36(5)54(83)73-44(27-38-16-18-39(76)19-17-38)57(86)74-51(61(92)93)35(4)53(82)71-42(56(85)70-41)14-11-25-66-62(64)65/h8-10,12-13,15-19,21,26,33-36,40-47,51,76H,11,14,20,22-25,27-31,63H2,1-7H3,(H,67,84)(H,68,87)(H,69,77)(H,70,85)(H,71,82)(H,72,81)(H,73,83)(H,74,86)(H,79,80)(H,88,89)(H,90,91)(H,92,93)(H4,64,65,66)/b21-15+,32-26+/t33-,34-,35-,36+,40-,41-,42-,43+,44-,45-,46?,47-,51+/m0/s1",CKZRRTHAVWEPNI-ZXQDSRFFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-3-((carboxymethyl)amino)-3-oxopropyl)thio)methyl)-15-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802013,,10.1021/tx00029a002,https://pubs.acs.org/doi/abs/10.1021/tx00029a002,"Formation, characterization, and toxicity of the glutathione and cysteine conjugates of toxic heptapeptide microcystins;Chemical Research in Toxicology;5;5;;1992;journalArticle;10.1021/tx00029a002;Kondo, Fumio; Ikai, Yoshitomo; Oka, Hisao; Okumura, Masanao; Ishikawa, Naohisa; Harada, Kenichi; Matsuura, Kenji; Murata, Hideaki; Suzuki, Makoto",n.a.,n.a.,n.a.,"field sample, surface bloom collected from Lake Suwa, Japan","Semisynthetic. Kondo et al. prepared this compound synthetically, but anticipated in biological samples."
CyanoMetDB_2077,"[D-Leu1,Mdha-GS(O)H7]MC-LR",,,Microcystin,C62H97N13O19S,1360.57,1359.67444,O=C(N(C1([H])CS(C[C@@H](C(NCC(O)=O)=O)NC(CC[C@H](N)C(O)=O)=O)=O)C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](NC([C@@H](CC(C)C)NC1=O)=O)CC(C)C)=O)=O)=O)=O,"InChI=1S/C62H97N13O19S/c1-32(2)25-43-56(84)72-44(26-33(3)4)57(85)74-51(61(91)92)37(8)53(81)70-41(17-14-24-66-62(64)65)55(83)69-40(20-18-34(5)27-35(6)47(94-10)28-38-15-12-11-13-16-38)36(7)52(80)71-42(60(89)90)21-23-49(77)75(9)46(58(86)73-43)31-95(93)30-45(54(82)67-29-50(78)79)68-48(76)22-19-39(63)59(87)88/h11-13,15-16,18,20,27,32-33,35-37,39-47,51H,14,17,19,21-26,28-31,63H2,1-10H3,(H,67,82)(H,68,76)(H,69,83)(H,70,81)(H,71,80)(H,72,84)(H,73,86)(H,74,85)(H,78,79)(H,87,88)(H,89,90)(H,91,92)(H4,64,65,66)/b20-18+,34-27+/t35-,36-,37-,39-,40-,41-,42+,43+,44-,45-,46?,47-,51+,95?/m0/s1",BHNCNWZXUZEONF-YNKVSUOUSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-2-((((R)-2-((S)-4-amino-4-carboxybutanamido)-3-((carboxymethyl)amino)-3-oxopropyl)sulfinyl)methyl)-15-(3-guanidinopropyl)-5,8-diisobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801652,,10.1016/j.hal.2018.10.006,https://linkinghub.elsevier.com/retrieve/pii/S1568988318301525,"Analysis of free and metabolized microcystins in samples following a bird mortality event;Harmful Algae;80;;;2018;journalArticle;10.1016/j.hal.2018.10.006;Foss, Amanda J.; Miles, Christopher O.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Wilkins, Alistair L.; Rise, Frode; Jaabæk, J. Atle H.; McGowan, Peter C.; Aubel, Mark T.",n.a.,n.a.,n.a.,"field sample, Chesapeake Bay off Poplar Island, Maryland, USA of cyanobacteria bloom containing Microcystis ","Confirmed by semi-synthesis from [Leu1]MC-LR, not thiol reactive"
CyanoMetDB_2078,[D-Asp3]MC-RE,,,Microcystin,C47H68N10O14,997.08,996.4916469,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCC(O)=O)NC(C[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C47H68N10O14/c1-25(22-26(2)36(71-7)23-30-12-9-8-10-13-30)15-16-31-27(3)40(62)55-34(45(67)68)17-19-38(59)57(6)29(5)42(64)51-28(4)41(63)54-32(14-11-21-50-47(48)49)43(65)56-35(46(69)70)24-37(58)52-33(44(66)53-31)18-20-39(60)61/h8-10,12-13,15-16,22,26-28,31-36H,5,11,14,17-21,23-24H2,1-4,6-7H3,(H,51,64)(H,52,58)(H,53,66)(H,54,63)(H,55,62)(H,56,65)(H,60,61)(H,67,68)(H,69,70)(H4,48,49,50)/b16-15+,25-22+/t26-,27-,28+,31-,32-,33-,34+,35+,36-/m0/s1",UPXKDXCMCOZZFB-KAXOOBBASA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(2-carboxyethyl)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684957,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/15,,
CyanoMetDB_2079,MC-RE,,,Microcystin,C48H70N10O14,1011.11,1010.507297,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCC(O)=O)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C48H70N10O14/c1-25(23-26(2)36(72-8)24-31-13-10-9-11-14-31)16-17-32-27(3)40(62)56-35(46(68)69)18-20-37(59)58(7)30(6)43(65)52-29(5)42(64)55-33(15-12-22-51-48(49)50)45(67)57-39(47(70)71)28(4)41(63)54-34(44(66)53-32)19-21-38(60)61/h9-11,13-14,16-17,23,26-29,32-36,39H,6,12,15,18-22,24H2,1-5,7-8H3,(H,52,65)(H,53,66)(H,54,63)(H,55,64)(H,56,62)(H,57,67)(H,60,61)(H,68,69)(H,70,71)(H4,49,50,51)/b17-16+,25-23+/t26-,27-,28-,29+,32-,33-,34-,35+,36-,39+/m0/s1",KGCDSBLLONXKBZ-CGABAVKJSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(2-carboxyethyl)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684958,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,"AB2017/14, AB2017/15",,
CyanoMetDB_2080,MC-(H2)YG,,,Microcystin,C48H65N7O13,948.05,947.4640352,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC(CNC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC[C@@H](O)C=C3)=O)=O)=O)=O,"InChI=1S/C48H65N7O13/c1-26(22-27(2)38(68-8)24-32-12-10-9-11-13-32)14-19-35-28(3)43(60)52-36(47(64)65)20-21-40(58)55(7)31(6)45(62)50-30(5)44(61)53-37(23-33-15-17-34(56)18-16-33)46(63)54-41(48(66)67)29(4)42(59)49-25-39(57)51-35/h9-17,19,22,27-30,34-38,41,56H,6,18,20-21,23-25H2,1-5,7-8H3,(H,49,59)(H,50,62)(H,51,57)(H,52,60)(H,53,61)(H,54,63)(H,64,65)(H,66,67)/b19-14+,26-22+/t27-,28-,29-,30+,34-,35-,36+,37-,38-,41+/m0/s1",ZZJCPJLRGNEYDX-DELIWHFPSA-N,"(5R,8S,11R,12S,18S,19S,22R)-8-(((R)-4-hydroxycyclohexa-1,5-dien-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684959,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,
CyanoMetDB_2081,MC-RM,,,Microcystin,C48H72N10O12S,1013.17,1012.505189,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCSC)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCCNC(N)=N)=O)=O)=O)=O,"InChI=1S/C48H72N10O12S/c1-26(24-27(2)37(70-8)25-32-14-11-10-12-15-32)17-18-33-28(3)40(60)56-36(46(66)67)19-20-38(59)58(7)31(6)43(63)52-30(5)42(62)55-34(16-13-22-51-48(49)50)45(65)57-39(47(68)69)29(4)41(61)54-35(21-23-71-9)44(64)53-33/h10-12,14-15,17-18,24,27-30,33-37,39H,6,13,16,19-23,25H2,1-5,7-9H3,(H,52,63)(H,53,64)(H,54,61)(H,55,62)(H,56,60)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b18-17+,26-24+/t27-,28-,29-,30+,33-,34-,35-,36+,37-,39+/m0/s1",GCIDJNJNMDMVFQ-MCUDKQGFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(3-guanidinopropyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-15-(2-(methylthio)ethyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684960,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,
CyanoMetDB_2082,MC-(H2)YA,,,Microcystin,C49H67N7O13,962.08,961.4796852,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](C)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC[C@@H](O)C=C3)=O)=O)=O)=O,"InChI=1S/C49H67N7O13/c1-26(23-27(2)39(69-9)25-33-13-11-10-12-14-33)15-20-36-28(3)42(59)53-37(48(65)66)21-22-40(58)56(8)32(7)46(63)51-31(6)45(62)54-38(24-34-16-18-35(57)19-17-34)47(64)55-41(49(67)68)29(4)43(60)50-30(5)44(61)52-36/h10-18,20,23,27-31,35-39,41,57H,7,19,21-22,24-25H2,1-6,8-9H3,(H,50,60)(H,51,63)(H,52,61)(H,53,59)(H,54,62)(H,55,64)(H,65,66)(H,67,68)/b20-15+,26-23+/t27-,28-,29-,30-,31+,35-,36-,37+,38-,39-,41+/m0/s1",YEHMHZLOSXGLLR-NMBLAQOHSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(((R)-4-hydroxycyclohexa-1,5-dien-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684961,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,
CyanoMetDB_2083,MC-EE,,,Microcystin,C47H65N7O16,984.04,983.448779,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCC(O)=O)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CCC(O)=O)=O)=O)=O)=O,"InChI=1S/C47H65N7O16/c1-24(22-25(2)35(70-8)23-30-12-10-9-11-13-30)14-15-31-26(3)40(60)52-34(46(66)67)16-19-36(55)54(7)29(6)43(63)48-28(5)42(62)51-33(18-21-38(58)59)45(65)53-39(47(68)69)27(4)41(61)50-32(44(64)49-31)17-20-37(56)57/h9-15,22,25-28,31-35,39H,6,16-21,23H2,1-5,7-8H3,(H,48,63)(H,49,64)(H,50,61)(H,51,62)(H,52,60)(H,53,65)(H,56,57)(H,58,59)(H,66,67)(H,68,69)/b15-14+,24-22+/t25-,26-,27-,28+,31-,32-,33-,34+,35-,39+/m0/s1",DRSTXSHKTFWNFL-CUTXYPRISA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(2-carboxyethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684962,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,"AB2017/14, AB2017/15",,
CyanoMetDB_2084,[Asp3]MC-LE,,,Microcystin,C47H67N7O14,954.05,953.4745999,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCC(O)=O)NC(C[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C47H67N7O14/c1-25(2)21-35-45(63)53-36(47(66)67)24-38(55)49-33(18-20-40(57)58)44(62)50-32(16-15-26(3)22-27(4)37(68-9)23-31-13-11-10-12-14-31)28(5)41(59)51-34(46(64)65)17-19-39(56)54(8)30(7)43(61)48-29(6)42(60)52-35/h10-16,22,25,27-29,32-37H,7,17-21,23-24H2,1-6,8-9H3,(H,48,61)(H,49,55)(H,50,62)(H,51,59)(H,52,60)(H,53,63)(H,57,58)(H,64,65)(H,66,67)/b16-15+,26-22+/t27-,28-,29+,32-,33-,34+,35-,36+,37-/m0/s1",HQMYLLJIOJVPHJ-DLGNEXPNSA-N,"(5R,8S,11R,15S,18S,19S,22R)-15-(2-carboxyethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684963,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,"AB2017/14, AB2017/15",,
CyanoMetDB_2085,MC-LE,,,Microcystin,C48H69N7O14,968.08,967.4902499,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCC(O)=O)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C48H69N7O14/c1-25(2)22-36-46(64)54-40(48(67)68)29(6)42(60)51-34(19-21-39(57)58)45(63)50-33(17-16-26(3)23-27(4)37(69-10)24-32-14-12-11-13-15-32)28(5)41(59)52-35(47(65)66)18-20-38(56)55(9)31(8)44(62)49-30(7)43(61)53-36/h11-17,23,25,27-30,33-37,40H,8,18-22,24H2,1-7,9-10H3,(H,49,62)(H,50,63)(H,51,60)(H,52,59)(H,53,61)(H,54,64)(H,57,58)(H,65,66)(H,67,68)/b17-16+,26-23+/t27-,28-,29-,30+,33-,34-,35+,36-,37-,40+/m0/s1",OYGLUIQXUNEURB-BRMCJMJMSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(2-carboxyethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684964,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,"AB2017/14, AB2017/15",,
CyanoMetDB_2086,MC-HilA,,,Microcystin,C47H69N7O12,924.07,923.5004207,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](C)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)C[C@@H](C)CC)=O)=O)=O)=O,"InChI=1S/C47H69N7O12/c1-12-25(2)23-36-45(61)53-39(47(64)65)29(6)41(57)48-30(7)42(58)50-34(19-18-26(3)22-27(4)37(66-11)24-33-16-14-13-15-17-33)28(5)40(56)51-35(46(62)63)20-21-38(55)54(10)32(9)44(60)49-31(8)43(59)52-36/h13-19,22,25,27-31,34-37,39H,9,12,20-21,23-24H2,1-8,10-11H3,(H,48,57)(H,49,60)(H,50,58)(H,51,56)(H,52,59)(H,53,61)(H,62,63)(H,64,65)/b19-18+,26-22+/t25-,27-,28-,29-,30-,31+,34-,35+,36-,37-,39+/m0/s1",WWIGXTSAJMYWND-JSIJJRETSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684965,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,
CyanoMetDB_2087,MC-HilAba,MC-HilAbu,,Microcystin,C48H71N7O12,938.1,937.5160707,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CC)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)C[C@@H](C)CC)=O)=O)=O)=O,"InChI=1S/C48H71N7O12/c1-12-26(3)24-37-46(62)54-40(48(65)66)30(7)42(58)50-34(13-2)45(61)51-35(20-19-27(4)23-28(5)38(67-11)25-33-17-15-14-16-18-33)29(6)41(57)52-36(47(63)64)21-22-39(56)55(10)32(9)44(60)49-31(8)43(59)53-37/h14-20,23,26,28-31,34-38,40H,9,12-13,21-22,24-25H2,1-8,10-11H3,(H,49,60)(H,50,58)(H,51,61)(H,52,57)(H,53,59)(H,54,62)(H,63,64)(H,65,66)/b20-19+,27-23+/t26-,28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1",RHSLRMNOYRZULY-LKKIUZQFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-ethyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-8-((S)-2-methylbutyl)-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684966,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,
CyanoMetDB_2088,MC-FV,,,Microcystin,C51H69N7O12,972.12,971.5004207,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](C(C)C)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CC=CC=C3)=O)=O)=O)=O,"InChI=1S/C51H69N7O12/c1-28(2)42-49(65)53-37(22-21-29(3)25-30(4)40(70-10)27-36-19-15-12-16-20-36)31(5)44(60)54-38(50(66)67)23-24-41(59)58(9)34(8)47(63)52-33(7)46(62)55-39(26-35-17-13-11-14-18-35)48(64)57-43(51(68)69)32(6)45(61)56-42/h11-22,25,28,30-33,37-40,42-43H,8,23-24,26-27H2,1-7,9-10H3,(H,52,63)(H,53,65)(H,54,60)(H,55,62)(H,56,61)(H,57,64)(H,66,67)(H,68,69)/b22-21+,29-25+/t30-,31-,32-,33+,37-,38+,39-,40-,42-,43+/m0/s1",WUWYXSBHLMCHEO-LKCZJABDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-benzyl-15-isopropyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684967,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,
CyanoMetDB_2089,MC-WV,,,Microcystin,C53H70N8O12,1011.15,1010.51132,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](C(C)C)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC3=CNC4=C3C=CC=C4)=O)=O)=O)=O,"InChI=1S/C53H70N8O12/c1-28(2)44-51(68)56-38(21-20-29(3)24-30(4)42(73-10)25-35-16-12-11-13-17-35)31(5)46(63)57-40(52(69)70)22-23-43(62)61(9)34(8)49(66)55-33(7)48(65)58-41(26-36-27-54-39-19-15-14-18-37(36)39)50(67)60-45(53(71)72)32(6)47(64)59-44/h11-21,24,27-28,30-33,38,40-42,44-45,54H,8,22-23,25-26H2,1-7,9-10H3,(H,55,66)(H,56,68)(H,57,63)(H,58,65)(H,59,64)(H,60,67)(H,69,70)(H,71,72)/b21-20+,29-24+/t30-,31-,32-,33+,38-,40+,41-,42-,44-,45+/m0/s1",UFZRCMUIGPFEPT-CGEDUOAOSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-((1H-indol-3-yl)methyl)-15-isopropyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",146684968,,10.3390/toxins12040232,https://www.mdpi.com/2072-6651/12/4/232,"Cylindrospermopsin- and Deoxycylindrospermopsin-Producing Raphidiopsis raciborskii and Microcystin-Producing Microcystis spp. in Meiktila Lake, Myanmar;Toxins;12;4;;2020;journalArticle;10.3390/toxins12040232;Ballot, Andreas; Swe, Thida; Mjelde, Marit; Cerasino, Leonardo; Hostyeva, Vladyslava; Miles, Christopher O.",Microcystis,n.a.,AB2017/14,,
CyanoMetDB_2090,"[Asp3,Mdha-unknown]MC-RR ",,,Microcystin,C93H145N21O33S,2117.15,2116.00344,,,,,,,10.3390/md17110643,https://www.mdpi.com/1660-3397/17/11/643,"Novel Microcystins from Planktothrix prolifica NIVA-CYA 544 Identified by LC-MS/MS, Functional Group Derivatization and 15N-labeling;Marine Drugs;17;11;;2019;journalArticle;10.3390/md17110643;Mallia, Vittoria; Uhlig, Silvio; Rafuse, Cheryl; Meija, Juris; Miles, Christopher O.",Planktothrix,prolifica,NIVA-CYA 544,,"only the miscrcoystin part of the molecule is structurally known, the conjugated portion has not been identified to date (July 2020)"
CyanoMetDB_2140,[D-Ser1]MC-LA,,,Microcystin,C46H67N7O13,926.06,925.479685,O=C(N(C)C(C(N[C@@H](C1=O)CO)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](C)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C46H67N7O13/c1-24(2)20-34-43(60)52-38(46(64)65)28(6)40(57)47-29(7)41(58)48-32(17-16-25(3)21-26(4)36(66-10)22-31-14-12-11-13-15-31)27(5)39(56)49-33(45(62)63)18-19-37(55)53(9)30(8)42(59)51-35(23-54)44(61)50-34/h11-17,21,24,26-29,32-36,38,54H,8,18-20,22-23H2,1-7,9-10H3,(H,47,57)(H,48,58)(H,49,56)(H,50,61)(H,51,59)(H,52,60)(H,62,63)(H,64,65)/b17-16+,25-21+/t26-,27-,28-,29-,32-,33+,34-,35+,36-,38+/m0/s1",PDWZTSUQEQIELX-VSFOPFNBSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-5-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,15,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802261,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,"Thiol-reactive, reported in dietary supplement"
CyanoMetDB_2141,[NMe-Ser7]MC-LA,[Mser7]MC-LA,,Microcystin,C46H69N7O13,928.08,927.4953353,O=C(N(C)[C@@H](CO)C(N[C@@H](C1=O)C)=O)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC2=CC=CC=C2)NC([C@H](C)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C46H69N7O13/c1-24(2)20-34-43(60)52-38(46(64)65)28(6)40(57)47-29(7)41(58)49-32(17-16-25(3)21-26(4)36(66-10)22-31-14-12-11-13-15-31)27(5)39(56)50-33(45(62)63)18-19-37(55)53(9)35(23-54)44(61)48-30(8)42(59)51-34/h11-17,21,24,26-30,32-36,38,54H,18-20,22-23H2,1-10H3,(H,47,57)(H,48,61)(H,49,58)(H,50,56)(H,51,59)(H,52,60)(H,62,63)(H,64,65)/b17-16+,25-21+/t26-,27-,28-,29-,30+,32-,33+,34-,35-,36-,38+/m0/s1",XJANOPPLSDSWNH-XEBJKPBESA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-2-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,15,19-pentamethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802417,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,Not thiol-reactive
CyanoMetDB_2142,[dm(1)Adda5]MC-LR,[8-desmethylAdda5]MC-LR,,Microcystin,C48H72N10O12,981.15,980.5331181,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/C[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)CC(C)C)=O)=O)=O)=O,"InChI=1S/C48H72N10O12/c1-26(2)24-37-45(65)57-39(47(68)69)29(5)41(61)54-35(16-13-23-51-48(49)50)44(64)53-34(20-18-27(3)17-19-33(70-9)25-32-14-11-10-12-15-32)28(4)40(60)55-36(46(66)67)21-22-38(59)58(8)31(7)43(63)52-30(6)42(62)56-37/h10-12,14-15,17-18,20,26,28-30,33-37,39H,7,13,16,19,21-25H2,1-6,8-9H3,(H,52,63)(H,53,64)(H,54,61)(H,55,60)(H,56,62)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b20-18+,27-17+/t28-,29-,30+,33+,34-,35-,36+,37-,39+/m0/s1",IPPFKMQSFNLDEL-WCJDNOPASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-isobutyl-18-((R,1E,3E)-6-methoxy-3-methyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802111,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,"algal dietary supplements; Position of de-methylation on Adda not fully defined - InChI and SMILES corresponding to [(8-desmethyl)-Adda]MC-LR. Position of de-methylation on Adda not fully defined (2, 6 or 8-position), but distinct from O-demethyl; thiol-reactive; dietary supplement. Stereochemistry assumed based on other MC congeners."
CyanoMetDB_2143,[dm(2)Adda5]MC-LR,[(6-desmethyl)-Adda5]MC-LR,,Microcystin,C48H72N10O12,981.15,980.5331181,CC(C)C[C@@H]1NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@H](\C=C\C=C\[C@H](C)[C@H](Cc2ccccc2)OC)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC1=O)C(=O)O)C(=O)O,"InChI=1S/C48H72N10O12/c1-26(2)24-36-45(65)57-39(47(68)69)29(5)41(61)54-34(20-15-23-51-48(49)50)44(64)53-33(19-14-13-16-27(3)37(70-9)25-32-17-11-10-12-18-32)28(4)40(60)55-35(46(66)67)21-22-38(59)58(8)31(7)43(63)52-30(6)42(62)56-36/h10-14,16-19,26-30,33-37,39H,7,15,20-25H2,1-6,8-9H3,(H,52,63)(H,53,64)(H,54,61)(H,55,60)(H,56,62)(H,57,65)(H,66,67)(H,68,69)(H4,49,50,51)/b16-13+,19-14+/t27-,28-,29-,30+,33-,34-,35+,36-,37-,39+/m0/s1",XOMCQYCXQBXGJI-JHGSTUCVSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-18-((1E,3E,5S,6S)-7-(cyclohexa-2,4-dien-1-yl)-6-methoxy-5-methylhepta-1,3-dien-1-yl)-15-(3-guanidinopropyl)-8-isobutyl-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802422,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,"algal dietary supplements; Position of de-methylation on Adda not fully defined - InChI and SMILES corresponding to [(6-desmethyl)-Adda]MC-LR. Position of de-methylation on Adda not fully defined (2, 6 or 8-position), but distinct from O-demethyl; thiol-reactive; dietary supplement. Stereochemistry assumed based on other MC congeners."
CyanoMetDB_2144,[D-Aba1]MC-LR,[D-Abu1]MC-LR,,Microcystin,C50H76N10O12,1009.2,1008.564418,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C50H76N10O12/c1-11-34-45(65)58-38(24-27(2)3)47(67)59-41(49(70)71)31(7)43(63)56-36(18-15-23-53-50(51)52)46(66)55-35(20-19-28(4)25-29(5)39(72-10)26-33-16-13-12-14-17-33)30(6)42(62)57-37(48(68)69)21-22-40(61)60(9)32(8)44(64)54-34/h12-14,16-17,19-20,25,27,29-31,34-39,41H,8,11,15,18,21-24,26H2,1-7,9-10H3,(H,54,64)(H,55,66)(H,56,63)(H,57,62)(H,58,65)(H,59,67)(H,68,69)(H,70,71)(H4,51,52,53)/b20-19+,28-25+/t29-,30-,31-,34+,35-,36-,37+,38-,39-,41+/m0/s1",HZMZGNIOSQSPQA-PTZXCAQDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-5-ethyl-15-(3-guanidinopropyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802105,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,algal dietary supplements; Stereochemistry assumed based on other MC congeners.
CyanoMetDB_2145,[D-Ser1]MC-LR,,,Microcystin,C49H74N10O13,1011.17,1010.543682,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CO)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C49H74N10O13/c1-26(2)22-36-45(66)58-40(48(70)71)30(6)42(63)54-34(16-13-21-52-49(50)51)44(65)53-33(18-17-27(3)23-28(4)38(72-9)24-32-14-11-10-12-15-32)29(5)41(62)55-35(47(68)69)19-20-39(61)59(8)31(7)43(64)57-37(25-60)46(67)56-36/h10-12,14-15,17-18,23,26,28-30,33-38,40,60H,7,13,16,19-22,24-25H2,1-6,8-9H3,(H,53,65)(H,54,63)(H,55,62)(H,56,67)(H,57,64)(H,58,66)(H,68,69)(H,70,71)(H4,50,51,52)/b18-17+,27-23+/t28-,29-,30-,33-,34-,35+,36-,37+,38-,40+/m0/s1",ILNAPLHZKJXPGS-GLDHPBRASA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-5-(hydroxymethyl)-8-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802109,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,algal dietary supplements; Stereochemistry assumed based on other MC congeners.
CyanoMetDB_2146,[dm(1)Adda5]MC-(H4)YR (isomer 1),[8-desmethylAdda5]MC-(H4)YR,,Microcystin,C51H74N10O13,1035.19,1034.543682,O=C(N(C)C(C(N[C@@H](C1=O)C)=O)=C)CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/C[C@@H](OC)CC2=CC=CC=C2)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N1)C[C@]3(C=C[C@@H](CC3)O)[H])=O)=O)=O)=O,"InChI=1S/C51H74N10O13/c1-28(15-21-36(74-7)26-33-12-9-8-10-13-33)16-22-37-29(2)43(64)58-39(49(70)71)23-24-41(63)61(6)32(5)46(67)55-31(4)45(66)59-40(27-34-17-19-35(62)20-18-34)48(69)60-42(50(72)73)30(3)44(65)57-38(47(68)56-37)14-11-25-54-51(52)53/h8-10,12-13,15-17,19,22,29-31,34-40,42,62H,5,11,14,18,20-21,23-27H2,1-4,6-7H3,(H,55,67)(H,56,68)(H,57,65)(H,58,64)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b22-16+,28-15+/t29-,30-,31+,34-,35-,36+,37-,38-,39+,40-,42+/m0/s1",XTXGUDSXHCIBAB-ZAKJOZQWSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-18-((R,1E,3E)-6-methoxy-3-methyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802426,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,algal dietary supplements; Stereochemistry assumed based on other MC congeners. Position of demethylation of Adda moiety is assumed (at position 8) but is distinct from the DMAdda moiety.
CyanoMetDB_2147,[dm(1)Adda5]MC-(H4)YR (isomer 2),[8-desmethylAdda5]MC-(H4)YR,,Microcystin,C51H74N10O13,1035.19,1034.543682,O[C@H]1C=C[C@@H](CC1)C[C@@H]1NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@@H](C)[C@H](\C=C\C=C\[C@H](C)[C@H](Cc2ccccc2)OC)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC1=O)C(=O)O)C(=O)O,"InChI=1S/C51H74N10O13/c1-28(40(74-7)27-33-15-9-8-10-16-33)14-11-12-17-36-29(2)43(64)58-38(49(70)71)23-24-41(63)61(6)32(5)46(67)55-31(4)45(66)59-39(26-34-19-21-35(62)22-20-34)48(69)60-42(50(72)73)30(3)44(65)57-37(47(68)56-36)18-13-25-54-51(52)53/h8-12,14-17,19,21,28-31,34-40,42,62H,5,13,18,20,22-27H2,1-4,6-7H3,(H,55,67)(H,56,68)(H,57,65)(H,58,64)(H,59,66)(H,60,69)(H,70,71)(H,72,73)(H4,52,53,54)/b14-11+,17-12+/t28-,29-,30-,31+,34-,35-,36-,37-,38+,39-,40-,42+/m0/s1",UHJPJYAHOVURPB-AGUNYHBDSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-5-methyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802354,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,algal dietary supplements; Stereochemistry assumed based on other MC congeners. Position of demethylation of Adda moiety is assumed (at position 6) but is distinct from the DMAdda moiety.
CyanoMetDB_2148,MC-(H4)Y(H4)Y,,,Microcystin,C55H77N7O14,1060.24,1059.55285,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](C[C@H]2C=C[C@H](O)CC2)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@H](C[C@H]2C=C[C@H](O)CC2)NC(=O)[C@@H](C)NC(=O)C(=C)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C55H77N7O14/c1-30(26-31(2)45(76-8)29-36-12-10-9-11-13-36)14-23-41-32(3)48(66)58-42(54(72)73)24-25-46(65)62(7)35(6)51(69)56-34(5)50(68)60-44(28-38-17-21-40(64)22-18-38)53(71)61-47(55(74)75)33(4)49(67)59-43(52(70)57-41)27-37-15-19-39(63)20-16-37/h9-15,17,19,21,23,26,31-34,37-45,47,63-64H,6,16,18,20,22,24-25,27-29H2,1-5,7-8H3,(H,56,69)(H,57,70)(H,58,66)(H,59,67)(H,60,68)(H,61,71)(H,72,73)(H,74,75)/b23-14+,30-26+/t31-,32-,33-,34+,37-,38-,39-,40-,41-,42+,43-,44-,45-,47+/m0/s1",IGYARPDFSSTKEZ-BQADBAKWSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802106,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,algal dietary supplements; Stereochemistry assumed based on other MC congeners. Position of hydroxyl group on tyrosine is assumed based on work of Parker et al. (2012).
CyanoMetDB_2149,[NMe-Ser7]MC-(H4)YR,[Mser7]MC-(H4)YR,,Microcystin,C52H78N10O14,1067.23,1066.569897,C[C@@H](\C=C(/C)\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](C)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](CO)N(C)C(=O)CC[C@@H](NC(=O)[C@H]1C)C(=O)O)C[C@H]1C=C[C@H](O)CC1)C(=O)O)[C@H](Cc1ccccc1)OC,"InChI=1S/C52H78N10O14/c1-28(24-29(2)41(76-7)26-33-12-9-8-10-13-33)15-20-36-30(3)44(66)59-38(50(72)73)21-22-42(65)62(6)40(27-63)49(71)56-32(5)46(68)60-39(25-34-16-18-35(64)19-17-34)48(70)61-43(51(74)75)31(4)45(67)58-37(47(69)57-36)14-11-23-55-52(53)54/h8-10,12-13,15-16,18,20,24,29-32,34-41,43,63-64H,11,14,17,19,21-23,25-27H2,1-7H3,(H,56,71)(H,57,69)(H,58,67)(H,59,66)(H,60,68)(H,61,70)(H,72,73)(H,74,75)(H4,53,54,55)/b20-15+,28-24+/t29-,30-,31-,32+,34-,35-,36-,37-,38+,39-,40-,41-,43+/m0/s1",DUDXLMLOMGZROM-KMPCJAIMSA-N,"(2S,5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(((1S,4R)-4-hydroxycyclohex-2-en-1-yl)methyl)-2-(hydroxymethyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155802037,,10.1016/j.phytochem.2012.03.005,https://pubs.acs.org/doi/10.1021/acs.jafc.0c02024,"Microcystin Toxins at Potentially Hazardous Levels in Algal Dietary Supplements Revealed by a Combination of Bioassay, Immunoassay, and Mass Spectrometric Methods;Journal of Agricultural and Food Chemistry;;;;2020;journalArticle;10.1021/acs.jafc.0c02024;Miller, Todd R.; Xiong, Ame; Deeds, Jonathan R.; Stutts, Whitney L.; Samdal, Ingunn A.; Løvberg, Kjersti E.; Miles, Christopher O.",n.a.,n.a.,n.a.,,algal dietary supplements; Stereochemistry assumed based on other MC congeners. Position of hydroxyl group on tyrosine is assumed based on work of Parker et al. (2012).
CyanoMetDB_2176,MC-AhppaAhppa,,,Microcystin,C59H77N7O14,1108.3,1107.55285,O=C(CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)NC([C@H](CCCC2=CC=C(O)C=C2)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N3)CCCC4=CC=C(O)C=C4)=O)=O)=O)=O)N(C)C(C(N[C@@H](C3=O)C)=O)=C,"InChI=1S/C59H77N7O14/c1-34(32-35(2)49(80-8)33-42-14-10-9-11-15-42)20-29-45-36(3)52(70)64-48(58(76)77)30-31-50(69)66(7)39(6)55(73)60-38(5)54(72)63-47(19-13-17-41-23-27-44(68)28-24-41)57(75)65-51(59(78)79)37(4)53(71)62-46(56(74)61-45)18-12-16-40-21-25-43(67)26-22-40/h9-11,14-15,20-29,32,35-38,45-49,51,67-68H,6,12-13,16-19,30-31,33H2,1-5,7-8H3,(H,60,73)(H,61,74)(H,62,71)(H,63,72)(H,64,70)(H,65,75)(H,76,77)(H,78,79)/b29-20+,34-32+/t35-,36-,37-,38+,45-,46-,47-,48+,49-,51+/m0/s1",BTTNRPYLPGDHOC-HRTZVOIPSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-(4-hydroxyphenyl)propyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",155801668,,10.1021/acs.jnatprod.7b00986,https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00986,"Microcystins Containing Doubly Homologated Tyrosine Residues from a Microcystis aeruginosa Bloom: Structures and Cytotoxicity;Journal of Natural Products;6;81;2018;journalArticle;10.1021/acs.jnatprod.7b00986;He, Haiyin; Wu, ShiBiao; Wahome, Paul G.; Bertin, Matthew J.; Pedone, Anna C.; Beauchesne, Kevin R.; Moeller, Peter D. R.; Carter, Guy T.",Microcystis ,aeruginosa,"field sample, bloom of Microcystis aeruginosa",,
CyanoMetDB_2177,MC-AhppaR,,,Microcystin,C54H76N10O13,1073.26,1072.55933,O=C(CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)NC([C@H](CCCNC(N)=N)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N2)CCCC3=CC=C(O)C=C3)=O)=O)=O)=O)N(C)C(C(N[C@@H](C2=O)C)=O)=C,"InChI=1S/C54H76N10O13/c1-30(28-31(2)43(77-8)29-37-14-10-9-11-15-37)19-24-39-32(3)46(67)62-42(52(73)74)25-26-44(66)64(7)35(6)49(70)58-34(5)48(69)61-40(17-12-16-36-20-22-38(65)23-21-36)51(72)63-45(53(75)76)33(4)47(68)60-41(50(71)59-39)18-13-27-57-54(55)56/h9-11,14-15,19-24,28,31-34,39-43,45,65H,6,12-13,16-18,25-27,29H2,1-5,7-8H3,(H,58,70)(H,59,71)(H,60,68)(H,61,69)(H,62,67)(H,63,72)(H,73,74)(H,75,76)(H4,55,56,57)/b24-19+,30-28+/t31-,32-,33-,34+,39-,40-,41-,42+,43-,45+/m0/s1",WWYZEFPPLXTSCI-FQEDTQHSSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-15-(3-guanidinopropyl)-8-(3-(4-hydroxyphenyl)propyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",145950954,,10.1021/acs.jnatprod.7b00986,https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00986,"Microcystins Containing Doubly Homologated Tyrosine Residues from a Microcystis aeruginosa Bloom: Structures and Cytotoxicity;Journal of Natural Products;6;81;2018;journalArticle;10.1021/acs.jnatprod.7b00986;He, Haiyin; Wu, ShiBiao; Wahome, Paul G.; Bertin, Matthew J.; Pedone, Anna C.; Beauchesne, Kevin R.; Moeller, Peter D. R.; Carter, Guy T.",Microcystis ,aeruginosa,"field sample, bloom of Microcystis aeruginosa",,
CyanoMetDB_2178,MC-HtyAhppa,,,Microcystin,C58H75N7O14,1094.27,1093.5372,O=C(CC[C@H](C(O)=O)NC([C@@H](C)[C@H](/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)NC([C@H](CCCC2=CC=C(O)C=C2)NC([C@@H](C)[C@H](C(O)=O)NC([C@@H](N3)CCC4=CC=C(O)C=C4)=O)=O)=O)=O)N(C)C(C(N[C@@H](C3=O)C)=O)=C,"InChI=1S/C58H75N7O14/c1-33(31-34(2)48(79-8)32-41-13-10-9-11-14-41)17-27-44-35(3)51(69)63-47(57(75)76)29-30-49(68)65(7)38(6)54(72)59-37(5)53(71)62-46(28-22-40-20-25-43(67)26-21-40)56(74)64-50(58(77)78)36(4)52(70)61-45(55(73)60-44)16-12-15-39-18-23-42(66)24-19-39/h9-11,13-14,17-21,23-27,31,34-37,44-48,50,66-67H,6,12,15-16,22,28-30,32H2,1-5,7-8H3,(H,59,72)(H,60,73)(H,61,70)(H,62,71)(H,63,69)(H,64,74)(H,75,76)(H,77,78)/b27-17+,33-31+/t34-,35-,36-,37+,44-,45-,46-,47+,48-,50+/m0/s1",NNMCUUKHSDLGJQ-PBKVJRLFSA-N,"(5R,8S,11R,12S,15S,18S,19S,22R)-8-(4-hydroxyphenethyl)-15-(3-(4-hydroxyphenyl)propyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,5,12,19-tetramethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid",145958986,,10.1021/acs.jnatprod.7b00986,https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00986,"Microcystins Containing Doubly Homologated Tyrosine Residues from a Microcystis aeruginosa Bloom: Structures and Cytotoxicity;Journal of Natural Products;6;81;2018;journalArticle;10.1021/acs.jnatprod.7b00986;He, Haiyin; Wu, ShiBiao; Wahome, Paul G.; Bertin, Matthew J.; Pedone, Anna C.; Beauchesne, Kevin R.; Moeller, Peter D. R.; Carter, Guy T.",Microcystis ,aeruginosa,"field sample, bloom of Microcystis aeruginosa",,