CHEBI:23527 - cytochalasin B

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ChEBI Name cytochalasin B
ChEBI ID CHEBI:23527
Definition An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C29H37NO5
Net Charge 0
Average Mass 479.60780
Monoisotopic Mass 479.26717
InChI InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
InChIKey GBOGMAARMMDZGR-TYHYBEHESA-N
SMILES [H][C@@]12\C=C\C[C@H](C)CCC[C@@H](O)\C=C\C(=O)O[C@]11C(=O)N[C@@H](Cc3ccccc3)[C@]1([H])[C@H](C)C(=C)[C@H]2O
Roles Classification
Biological Role(s): mycotoxin
Poisonous substance produced by fungi.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
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ChEBI Ontology
Outgoing cytochalasin B (CHEBI:23527) has role metabolite (CHEBI:25212)
cytochalasin B (CHEBI:23527) has role mycotoxin (CHEBI:25442)
cytochalasin B (CHEBI:23527) has role platelet aggregation inhibitor (CHEBI:50427)
cytochalasin B (CHEBI:23527) is a cytochalasin (CHEBI:23528)
cytochalasin B (CHEBI:23527) is a lactam (CHEBI:24995)
cytochalasin B (CHEBI:23527) is a lactone (CHEBI:25000)
cytochalasin B (CHEBI:23527) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name
(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
Synonym Source
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Manual Xrefs Databases
C19954 KEGG COMPOUND
Cytochalasin_B Wikipedia
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Registry Numbers Types Sources
1096210 Reaxys Registry Number Reaxys
14930-96-2 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
22882828 PubMed citation Europe PMC
Last Modified
09 June 2014