CHEBI:88049 - 7-epi-cylindrospermopsin

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ChEBI Name 7-epi-cylindrospermopsin
ChEBI ID CHEBI:88049
ChEBI ASCII Name 7-epi-cylindrospermopsin
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.
Stars This entity has been manually annotated by the ChEBI Team.
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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-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]
Metabolite of Species Details
Oscillatoria sp. (NCBI:txid1159) of strain PCC 6506 See: PubMed
Aphanizomenon ovalisporum (NCBI:txid75695) 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.
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 exihibiting 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.
(via alkaloid )
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ChEBI Ontology
Outgoing 7-epi-cylindrospermopsin (CHEBI:88049) has role cyanotoxin (CHEBI:88048)
7-epi-cylindrospermopsin (CHEBI:88049) has role genotoxin (CHEBI:50902)
7-epi-cylindrospermopsin (CHEBI:88049) has role hepatotoxic agent (CHEBI:50908)
7-epi-cylindrospermopsin (CHEBI:88049) has role protein synthesis inhibitor (CHEBI:48001)
7-epi-cylindrospermopsin (CHEBI:88049) is a alkaloid (CHEBI:22315)
7-epi-cylindrospermopsin (CHEBI:88049) is a cylindrospermopsins (CHEBI:88045)
7-epi-cylindrospermopsin (CHEBI:88049) is a organic sulfate (CHEBI:25704)
7-epi-cylindrospermopsin (CHEBI:88049) is a pyrimidone (CHEBI:38337)
7-epi-cylindrospermopsin (CHEBI:88049) is a secondary alcohol (CHEBI:35681)
7-epi-cylindrospermopsin (CHEBI:88049) is a triazaacenaphthylene (CHEBI:88047)
7-epi-cylindrospermopsin (CHEBI:88049) is tautomer of 7-epi-cylindrospermopsin zwitterion (CHEBI:143707)
Incoming 7-epi-cylindrospermopsin zwitterion (CHEBI:143707) is tautomer of 7-epi-cylindrospermopsin (CHEBI:88049)
IUPAC Name
(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
Synonyms Sources
(-)-Epicyclindrospermopsin KNApSAcK
7-epicylindrospermopsin ChEBI
epicylindrospermopsin ChEBI
Manual Xrefs Databases
C00027774 KNApSAcK
Cylindrospermopsin Wikipedia
View more database links
Registry Number Type Source
265652-18-4 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
10757726 PubMed citation Europe PMC
11535093 PubMed citation Europe PMC
11942831 PubMed citation Europe PMC
11982346 PubMed citation Europe PMC
15170307 PubMed citation Europe PMC
20525864 PubMed citation Europe PMC
21404419 PubMed citation Europe PMC
Last Modified
29 September 2015