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CHEBI:2766 - aphidicolin

Default Structure
ChEBI IDCHEBI:2766
ChEBI Nameaphidicolin
Stars
DefinitionA 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.
Last Modified3 June 2021
DownloadsMolfile
FormulaC20H34O4
Net Charge0
Average Mass338.488
Monoisotopic Mass338.24571
SMILES[H][C@@]12CC[C@]3([H])[C@](C)(CC[C@@H](O)[C@@]3(C)CO)[C@]13CC[C@](O)(CO)[C@H](C2)C3
InChIInChI=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
InChIKeyNOFOAYPPHIUXJR-APNQCZIXSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Aspergillus oryzae (ncbitaxon:5062) - PubMed (29191129)
Cephalosporium aphidicola (ncbitaxon:291364) - PubMed (21812410)
Tolypocladium inflatum (ncbitaxon:29910) - PubMed (21812410) Ethylacetate extract and fungus isolated from a soil sample on fruiting body of Cordyceps sinensis
Roles Classification
Biological Roles:
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).
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
antimitotic  Any compound that inhibits cell division (mitosis).
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
aphidicolin (CHEBI:2766) has role Aspergillus metabolite (CHEBI:76956)
aphidicolin (CHEBI:2766) has role antimicrobial agent (CHEBI:33281)
aphidicolin (CHEBI:2766) has role antimitotic (CHEBI:64911)
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  Source
(3α,4α,5α,17α)-3,17-dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanolChEBI
AphidicolinKEGG COMPOUND
aphidocolinChEBI
Manual XrefsDatabases
10280269ChemSpider
2ZEPDBeChem
AphidicolinWikipedia
C00000873KNApSAcK
C06088KEGG COMPOUND
CPD-11426MetaCyc
LSM-45486LINCS
US3761512Patent
Registry NumbersSources
Reaxys:2055641Reaxys
Beilstein:4689958Beilstein
CAS:38966-21-1KEGG COMPOUND
CAS:38966-21-1ChemIDplus
Citations