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CHEBI:529996 - cytochalasin D

ChEBI IDCHEBI:529996
ChEBI Namecytochalasin D
Stars
DefinitionAn organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.
Last Modified7 February 2018
DownloadsMolfile
FormulaC30H37NO6
Net Charge0
Average Mass507.627
Monoisotopic Mass507.26209
SMILES[H][C@]12[C@H](Cc3ccccc3)NC(=O)[C@@]13C(/C=C/C[C@H](C)C(=O)[C@](C)(O)/C=C/[C@H]3OC(C)=O)[C@H](O)C(=C)[C@H]2C
InChIInChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/b13-9+,15-14+/t17-,18+,22?,23-,24+,25-,26+,29+,30+/m0/s1
InChIKeySDZRWUKZFQQKKV-FJUULPFHSA-N
Wikipedia
Roles Classification
Biological Roles:
actin polymerisation inhibitor  Any substance that inhibits the polymerisation of the protein actin.
mycotoxin  Poisonous substance produced by fungi.
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
cytochalasin D (CHEBI:529996) has role actin polymerisation inhibitor (CHEBI:70728)
cytochalasin D (CHEBI:529996) has role antineoplastic agent (CHEBI:35610)
cytochalasin D (CHEBI:529996) has role DNA synthesis inhibitor (CHEBI:59517)
cytochalasin D (CHEBI:529996) has role mycotoxin (CHEBI:25442)
cytochalasin D (CHEBI:529996) is a acetate ester (CHEBI:47622)
cytochalasin D (CHEBI:529996) is a alkaloid (CHEBI:22315)
cytochalasin D (CHEBI:529996) is a cyclic ketone (CHEBI:3992)
cytochalasin D (CHEBI:529996) is a cytochalasin (CHEBI:23528)
cytochalasin D (CHEBI:529996) is a organic heterotricyclic compound (CHEBI:26979)
cytochalasin D (CHEBI:529996) is a secondary alcohol (CHEBI:35681)
cytochalasin D (CHEBI:529996) is a tertiary alcohol (CHEBI:26878)
cytochalasin D (CHEBI:529996) is a tertiary α-hydroxy ketone (CHEBI:139592)
cytochalasin D (CHEBI:529996) is a γ-lactam (CHEBI:74222)
IUPAC Name 
(3S,3aR,4S,6S,7E,10S,12R,13E,15R,15aR)-3-benzyl-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-1,11-dioxo-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-1H-cycloundeca[d]isoindol-15-yl acetate
Synonyms  Source
Zygosporin AChemIDplus
Cytohalasin DChemIDplus
Lygosporin AChemIDplus
7,18-Dihydroxy-10-phenyl-5,16,18-trimethyl-(11)cytochalas-21-acetoxy-6(12),13,19-trien-17-oneChemIDplus
Manual XrefsDatabases
Cytochalasin_DWikipedia
CY9PDBeChem
Registry NumbersSources
Reaxys:1632828Reaxys
CAS:22144-77-0ChemIDplus
Citations