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CHEBI:23527 - cytochalasin B

Default Structure
ChEBI IDCHEBI:23527
ChEBI Namecytochalasin B
Stars
DefinitionAn organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.
Last Modified27 August 2021
DownloadsMolfile
FormulaC29H37NO5
Net Charge0
Average Mass479.617
Monoisotopic Mass479.26717
SMILES[H][C@]12[C@H](Cc3ccccc3)NC(=O)[C@]13OC(=O)/C=C/[C@H](O)CCC[C@@H](C)C/C=C/[C@@]3([H])[C@H](O)C(=C)[C@H]2C
InChIInChI=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
InChIKeyGBOGMAARMMDZGR-TYHYBEHESA-N
Wikipedia
Roles Classification
Biological Roles:
actin polymerisation inhibitor  Any substance that inhibits the polymerisation of the protein actin.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
mycotoxin  Poisonous substance produced by fungi.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
cytochalasin B (CHEBI:23527) has role actin polymerisation inhibitor (CHEBI:70728)
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
PhominChEBI
UniProt Name  Source
cytochalasin BUniProt
Manual XrefsDatabases
C00011322KNApSAcK
C19954KEGG COMPOUND
CPD-20745MetaCyc
Cytochalasin_BWikipedia
LMPK11000002LIPID MAPS
Registry NumbersSources
Reaxys:1096210Reaxys
CAS:14930-96-2ChemIDplus
Citations