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CHEBI:88046 - cylindrospermopsin

ChEBI IDCHEBI:88046
ChEBI Namecylindrospermopsin
Stars
DefinitionA 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.
Last Modified16 May 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC15H21N5O7S
Net Charge0
Average Mass415.428
Monoisotopic Mass415.11617
SMILES[H][C@@]12C[C@H](OS(=O)(=O)O)[C@H](C)[C@@]3([H])CN=C(N[C@@]([H])([C@@H](O)c4cc(=O)nc(=O)n4)C1)N23
InChIInChI=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
InChIKeyLHJPHMKIGRLKDR-VDPNAHCISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cylindrospermopsis raciborskii (ncbitaxon:77022) - PubMed (14559084)
Oscillatoria sp. (ncbitaxon:1159) - PubMed (20525864) Strain: PCC 6506
Aphanizomenon ovalisporum (ncbitaxon:75695) - PubMed (10757726)
Roles Classification
Biological Roles:
genotoxin  A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
hepatotoxic agent  A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
cyanotoxin  Any toxin produced by cyanobacteria (blue-green algae).
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
cylindrospermopsin (CHEBI:88046) has role cyanotoxin (CHEBI:88048)
cylindrospermopsin (CHEBI:88046) has role genotoxin (CHEBI:50902)
cylindrospermopsin (CHEBI:88046) has role hepatotoxic agent (CHEBI:50908)
cylindrospermopsin (CHEBI:88046) has role protein synthesis inhibitor (CHEBI:48001)
cylindrospermopsin (CHEBI:88046) is a alkaloid (CHEBI:22315)
cylindrospermopsin (CHEBI:88046) is a cylindrospermopsins (CHEBI:88045)
cylindrospermopsin (CHEBI:88046) is a organic sulfate (CHEBI:25704)
cylindrospermopsin (CHEBI:88046) is a pyrimidone (CHEBI:38337)
cylindrospermopsin (CHEBI:88046) is a secondary alcohol (CHEBI:35681)
cylindrospermopsin (CHEBI:88046) is a triazaacenaphthylene (CHEBI:88047)
cylindrospermopsin (CHEBI:88046) is tautomer of cylindrospermopsin zwitterion (CHEBI:88044)
Incoming Relation(s)
cylindrospermopsin zwitterion (CHEBI:88044) is tautomer of cylindrospermopsin (CHEBI:88046)
IUPAC Name 
(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
Synonyms  Source
(−)-cylindrospermopsinChEBI
CYNChEBI
CYLChEBI
Manual XrefsDatabases
CylindrospermopsinWikipedia
C19999KEGG COMPOUND
Registry NumbersSources
CAS:143545-90-8ChemIDplus
Citations