CHEBI:529996 - cytochalasin D

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ChEBI Name cytochalasin D
ChEBI ID CHEBI:529996
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C30H37NO6
Net Charge 0
Average Mass 507.61790
Monoisotopic Mass 507.26209
InChI InChI=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
InChIKey SDZRWUKZFQQKKV-FJUULPFHSA-N
SMILES [H][C@]12[C@H](Cc3ccccc3)NC(=O)[C@]11[C@H](OC(C)=O)\C=C\[C@@](C)(O)C(=O)[C@@H](C)C\C=C\C1[C@H](O)C(=C)[C@H]2C
Roles Classification
Biological Role(s): DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
mycotoxin
Poisonous substance produced by fungi.
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.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 γ-lactam (CHEBI:74222)
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 α-hydroxy ketone (CHEBI:139592)
cytochalasin D (CHEBI:529996) is a tertiary alcohol (CHEBI:26878)
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 Sources
7,18-Dihydroxy-10-phenyl-5,16,18-trimethyl-(11)cytochalas-21-acetoxy-6(12),13,19-trien-17-one ChemIDplus
Cytohalasin D ChemIDplus
Lygosporin A ChemIDplus
Zygosporin A ChemIDplus
Manual Xrefs Databases
CY9 PDBeChem
Cytochalasin_D Wikipedia
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Registry Numbers Types Sources
1632828 Reaxys Registry Number Reaxys
1632828 Beilstein Registry Number Beilstein
22144-77-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20010439 PubMed citation Europe PMC
22305779 PubMed citation Europe PMC
22684244 PubMed citation Europe PMC
22728040 PubMed citation Europe PMC
23615686 PubMed citation Europe PMC
5800426 PubMed citation Europe PMC
7199049 PubMed citation Europe PMC
Last Modified
07 February 2018