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CHEBI:2766 - aphidicolin

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
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
Aspergillus oryzae (ncbitaxon:5062) - PubMed (29191129)
Roles Classification
Biological Roles:
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
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).
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.
antimitotic  Any compound that inhibits cell division (mitosis).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
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
AphidicolinKEGG COMPOUND
aphidocolinChEBI
(3α,4α,5α,17α)-3,17-dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanolChEBI
Manual XrefsDatabases
C06088KEGG COMPOUND
CPD-11426MetaCyc
AphidicolinWikipedia
US3761512Patent
C00000873KNApSAcK
2ZEPDBeChem
LSM-45486LINCS
10280269ChemSpider
Registry NumbersSources
Reaxys:2055641Reaxys
Beilstein:4689958Beilstein
CAS:38966-21-1KEGG COMPOUND
CAS:38966-21-1ChemIDplus
Citations