CHEBI:142867 - andrastin C

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ChEBI Name andrastin C
ChEBI ID CHEBI:142867
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H40O6
Net Charge 0
Average Mass 472.615
Monoisotopic Mass 472.28249
InChI InChI=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
InChIKey COPIXBGZYYCWRA-QUQNHZJXSA-N
SMILES C1C[C@@H](C([C@@]2([C@@]1([C@]3([C@](CC2)([C@]4([C@@](C(=C3)C)(C(C(=C4O)C)=O)C)C(OC)=O)C)[H])C)[H])(C)C)OC(C)=O
Metabolite of Species Details
Penicillium camponotum (NCBI:txid2072477) See: PubMed
Penicillium cataractarum (NCBI:txid2100454) See: PubMed
Penicillium costaricense (NCBI:txid2100456) See: PubMed
Penicillium roqueforti (NCBI:txid5082) See: PubMed
Penicillium simplicissimum (NCBI:txid69488) of strain FO-3929 See: PubMed
Roles Classification
Biological Role(s): 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.
Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via meroterpenoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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-carboxylate IUPAC
Citations Waiting for Citations Types Sources
15826038 PubMed citation Europe PMC
23106671 PubMed citation Europe PMC
26863302 PubMed citation Europe PMC
8682716 PubMed citation Europe PMC
8682717 PubMed citation Europe PMC
Last Modified
09 January 2019