CHEBI:88046 - cylindrospermopsin

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ChEBI Name cylindrospermopsin
ChEBI ID CHEBI:88046
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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5110067, eMolecules:713318
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Formula C15H21N5O7S
Net Charge 0
Average Mass 415.423
Monoisotopic Mass 415.11617
InChI 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]
Metabolite of Species Details
Oscillatoria sp. (NCBI:txid1159) of strain PCC 6506 See: PubMed
Aphanizomenon ovalisporum (NCBI:txid75695) See: PubMed
Cylindrospermopsis raciborskii (NCBI:txid77022) See: PubMed
Roles Classification
Biological Role(s): 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.
hepatotoxic agent
A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing 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 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 Sources
(−)-cylindrospermopsin ChEBI
CYL ChEBI
CYN ChEBI
Manual Xrefs Databases
C19999 KEGG COMPOUND
Cylindrospermopsin Wikipedia
View more database links
Registry Number Type Source
143545-90-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11535093 PubMed citation Europe PMC
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Last Modified
16 May 2019