Term: | cylindrospermopsin |
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Accession: | CHEBI:88046
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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 R 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-[(R)-(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: | CYL; CYN; 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-VDPNAHCISA-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] |
| xref: | CAS:143545-90-8; KEGG:C19999 |
| xref_mesh: | MESH:C089595 |
| xref: | PMID:11535093; PMID:12635096; PMID:18440200; PMID:24000190; PMID:24477983; PMID:24846598; PMID:25219470; PMID:25553582; PMID:25575781; PMID:25639895; PMID:25661706; PMID:25768423; PMID:26091872; PMID:26191986; PMID:26209169; Wikipedia:Cylindrospermopsin |
| cyclic_relationship: | is_tautomer_of CHEBI:88044 |
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