CHEBI:2766 - aphidicolin

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ChEBI Name aphidicolin
ChEBI ID CHEBI:2766
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
InChIKey NOFOAYPPHIUXJR-APNQCZIXSA-N
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 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
A DNA polymerase inhibitor that interferes with the action of a DNA-directed DNA polymerase (EC 2.7.7.7).
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 2.7.7.7 (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)
IUPAC Name
(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol
Synonyms Sources
(3α,4α,5α,17α)-3,17-dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol ChEBI
Aphidicolin KEGG COMPOUND
aphidocolin
Note: (2015-04-15) rare variant spelling
ChEBI
Manual Xrefs Databases
Aphidicolin Wikipedia
C00000873 KNApSAcK
C00023944 KNApSAcK
C06088 KEGG COMPOUND
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