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Accession:CHEBI:88049 term browser browse the term
Definition:A triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer in which the carbon bearing the hydroxy group has S configuration). It is a cyanotoxin produced by several species of freshwater cyanobacteria, such as Aphanizomenon ovalisporum.
Synonyms:exact_synonym: (2aS,3R,4S,5aS,7R)-7-[(S)-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl]-3-methyl-2a,3,4,5,5a,6,7,8-octahydro-2H-1,8,8b-triazaacenaphthylen-4-yl hydrogen sulfate
 related_synonym: (-)-Epicyclindrospermopsin;   7-epicylindrospermopsin;   Formula=C15H21N5O7S;   InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/t6-,7+,8-,10-,11+,13+/m1/s1;   InChIKey=LHJPHMKIGRLKDR-YUQKHPEDSA-N;   SMILES=[C@@]12(C[C@@H]([C@@H]([C@@]3(N1C(N[C@](C2)([C@@H](C4=CC(NC(N4)=O)=O)O)[H])=NC3)[H])C)OS(O)(=O)=O)[H];   epicylindrospermopsin
 xref: CAS:265652-18-4 "KNApSAcK";   KNApSAcK:C00027774;   PMID:10757726 "Europe PMC";   PMID:11535093 "Europe PMC";   PMID:11942831 "Europe PMC";   PMID:11982346 "Europe PMC";   PMID:15170307 "Europe PMC";   PMID:20525864 "Europe PMC";   PMID:21404419 "Europe PMC";   Wikipedia:Cylindrospermopsin
 cyclic_relationship: is_tautomer_of CHEBI:143707

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  CHEBI ontology 19596
    role 19539
      biological role 19537
        aetiopathogenetic role 18679
          genotoxin 16021
            7-epi-cylindrospermopsin 0
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                                chalcogen oxoacid 11367
                                  sulfur oxoacid 10954
                                    sulfuric acid 7898
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