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CHEBI:88046 - cylindrospermopsin

Default Structure
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
Aphanizomenon ovalisporum (ncbitaxon:75695) - PubMed (10757726)
Cylindrospermopsis raciborskii (ncbitaxon:77022) - PubMed (14559084)
Oscillatoria sp. (ncbitaxon:1159) - PubMed (20525864) Strain: PCC 6506
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.
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.
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
CYLChEBI
(−)-cylindrospermopsinChEBI
CYNChEBI
Manual XrefsDatabases
C19999KEGG COMPOUND
CylindrospermopsinWikipedia
Registry NumbersSources
CAS:143545-90-8ChemIDplus
Citations