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CHEBI:142867 - andrastin C

ChEBI IDCHEBI:142867
ChEBI Nameandrastin C
Stars
DefinitionA 17-oxosteroid that is 17-oxo-5β,9β,10α,13α-androsta-11,15-dieneandroxta-11,15-diene which is substituted by an acetoxy group at the 3β position, methyl groups at the 4, 4, 8, 12, and 16 positions, a methoxycarbonyl group at position 14, and a hydroxy group at position 15. A farnesyltransferase inhibitor produced by Penicillium roqueforti, a filamentous fungus involved in the ripening of several kinds of blue cheeses.
Last Modified9 January 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC28H40O6
Net Charge0
Average Mass472.622
Monoisotopic Mass472.28249
SMILES[H][C@@]12C=C(C)[C@@]3(C)C(=O)C(C)=C(O)[C@@]3(C(=O)OC)[C@@]1(C)CC[C@]1([H])C(C)(C)[C@@H](OC(C)=O)CC[C@@]21C
InChIInChI=1S/C28H40O6/c1-15-14-19-25(6)12-11-20(34-17(3)29)24(4,5)18(25)10-13-26(19,7)28(23(32)33-9)22(31)16(2)21(30)27(15,28)8/h14,18-20,31H,10-13H2,1-9H3/t18-,19+,20+,25-,26+,27+,28-/m1/s1
InChIKeyCOPIXBGZYYCWRA-QUQNHZJXSA-N
Species of MetaboliteComponentSourceComments
Penicillium roqueforti (ncbitaxon:5082) - PubMed (15826038)
Penicillium simplicissimum (ncbitaxon:69488) - PubMed (8682716) Strain: FO-3929
Penicillium camponotum (ncbitaxon:2072477) - PubMed (27616792)
Penicillium cataractarum (ncbitaxon:2100454) - PubMed (27616792)
Penicillium costaricense (ncbitaxon:2100456) - PubMed (27616792)
Roles Classification
Biological Roles:
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
EC 2.5.1.58 (protein farnesyltransferase) inhibitor  An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein farnesyltransferase (EC 2.5.1.58), one of the three enzymes in the prenyltransferase group.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
andrastin C (CHEBI:142867) has role Penicillium metabolite (CHEBI:76964)
andrastin C (CHEBI:142867) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
andrastin C (CHEBI:142867) is a 15-hydroxy steroid (CHEBI:38089)
andrastin C (CHEBI:142867) is a 17-oxo steroid (CHEBI:19168)
andrastin C (CHEBI:142867) is a 5β steroid (CHEBI:136889)
andrastin C (CHEBI:142867) is a acetate ester (CHEBI:47622)
andrastin C (CHEBI:142867) is a enol (CHEBI:33823)
andrastin C (CHEBI:142867) is a meroterpenoid (CHEBI:64419)
andrastin C (CHEBI:142867) is a methyl ester (CHEBI:25248)
andrastin C (CHEBI:142867) is conjugate acid of andrastin C(1−) (CHEBI:142821)
Incoming Relation(s)
andrastin B (CHEBI:142862) has functional parent andrastin C (CHEBI:142867)
andrastin C(1−) (CHEBI:142821) is conjugate base of andrastin C (CHEBI:142867)
IUPAC Name 
methyl 3β-(acetyloxy)-15-hydroxy-4,4,8α,12,16-pentamethyl-17-oxo-5β,9β,10α,13α-androsta-11,15-diene-14-carboxylate
Synonym  Source
methyl (3β,5β,8α,9β,10α,13α)-3-(acetyloxy)-15-hydroxy-4,4,8,12,16-pentamethyl-17-oxoandrosta-11,15-diene-14-carboxylateIUPAC
Citations