CHEBI:2766 - aphidicolin

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ChEBI Name aphidicolin
Definition A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H34O4
Net Charge 0
Average Mass 338.482
Monoisotopic Mass 338.24571
InChI InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
SMILES [C@]12([C@]([C@@]([C@@H](CC1)O)(CO)C)(CC[C@@]3([C@@]24CC[C@]([C@H](C3)C4)(O)CO)[H])[H])C
Metabolite of Species Details
Cephalosporium aphidicola (NCBI:txid291364) See: PubMed
Tolypocladium inflatum (NCBI:txid29910) Ethylacetate extract and fungus isolated from a soil sample on fruiting body of Cordyceps sinensis See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
EC (DNA-directed DNA polymerase) inhibitor
A DNA polymerase inhibitor that interferes with the action of a DNA-directed DNA polymerase (EC
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aphidicolin (CHEBI:2766) has role antimicrobial agent (CHEBI:33281)
aphidicolin (CHEBI:2766) has role antineoplastic agent (CHEBI:35610)
aphidicolin (CHEBI:2766) has role antiviral drug (CHEBI:36044)
aphidicolin (CHEBI:2766) has role apoptosis inducer (CHEBI:68495)
aphidicolin (CHEBI:2766) has role DNA synthesis inhibitor (CHEBI:59517)
aphidicolin (CHEBI:2766) has role EC (DNA-directed DNA polymerase) inhibitor (CHEBI:131699)
aphidicolin (CHEBI:2766) has role fungal metabolite (CHEBI:76946)
aphidicolin (CHEBI:2766) is a tetracyclic diterpenoid (CHEBI:52557)
Synonyms Sources
(3α,4α,5α,17α)-3,17-dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol ChEBI
Note: (2015-04-15) rare variant spelling
Manual Xrefs Databases
Aphidicolin Wikipedia
C00000873 KNApSAcK
C00023944 KNApSAcK
CPD-11426 MetaCyc
US3761512 Patent
View more database links
Registry Numbers Types Sources
2055641 Reaxys Registry Number Reaxys
38966-21-1 CAS Registry Number KEGG COMPOUND
38966-21-1 CAS Registry Number ChemIDplus
4689958 Beilstein Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
07 April 2016