CHEBI:142874 - andrastin D

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ChEBI Name andrastin D
ChEBI ID CHEBI:142874
Definition A 3-oxo steroid that is andrastin C in which the acetoxy group at the 3beta position has undergone formal oxidative cleavage to afford the corresponding 3-oxo derivative. 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 C26H36O5
Net Charge 0
Average Mass 428.562
Monoisotopic Mass 428.25627
InChI InChI=1S/C26H36O5/c1-14-13-17-23(5)11-10-18(27)22(3,4)16(23)9-12-24(17,6)26(21(30)31-8)20(29)15(2)19(28)25(14,26)7/h13,16-17,29H,9-12H2,1-8H3/t16-,17+,23-,24+,25+,26-/m1/s1
InChIKey OVCUEWPSMQMSOY-UWWAQUNASA-N
SMILES C1CC(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)=O
Metabolite of Species Details
Penicillium camponotum (NCBI:txid2072477) See: PubMed
Penicillium cataractarum (NCBI:txid2100454) See: PubMed
Penicillium roqueforti (NCBI:txid5082) See: PubMed
Penicillium roqueforti (NCBI:txid5082) See: PubMed
Penicillium simplicissimum (NCBI:txid69488) of strain FO-3929 See: PubMed
Roles Classification
Biological Role(s): 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.
(via meroterpenoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing andrastin D (CHEBI:142874) has role Penicillium metabolite (CHEBI:76964)
andrastin D (CHEBI:142874) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
andrastin D (CHEBI:142874) is a 15-hydroxy steroid (CHEBI:38089)
andrastin D (CHEBI:142874) is a 17-oxo steroid (CHEBI:19168)
andrastin D (CHEBI:142874) is a 3-oxo steroid (CHEBI:47788)
andrastin D (CHEBI:142874) is a 5β steroid (CHEBI:136889)
andrastin D (CHEBI:142874) is a enol (CHEBI:33823)
andrastin D (CHEBI:142874) is a meroterpenoid (CHEBI:64419)
andrastin D (CHEBI:142874) is a methyl ester (CHEBI:25248)
andrastin D (CHEBI:142874) is conjugate acid of andrastin D(1−) (CHEBI:142819)
Incoming andrastin E (CHEBI:142875) has functional parent andrastin D (CHEBI:142874)
andrastin F (CHEBI:142878) has functional parent andrastin D (CHEBI:142874)
andrastin D(1−) (CHEBI:142819) is conjugate base of andrastin D (CHEBI:142874)
IUPAC Name
methyl 15-hydroxy-4,4,8α,12,16-pentamethyl-3,17-dioxo-5β,9β,10α,13α-androsta-11,15-diene-14-carboxylate
Synonym Source
methyl (5β,8α,9β,10α,13α)-15-hydroxy-4,4,8,12,16-pentamethyl-3,17-dioxoandrosta-11,15-diene-14-carboxylate IUPAC
Manual Xref Database
C00016286 KNApSAcK
View more database links
Registry Number Type Source
184432-08-4 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
15826038 PubMed citation Europe PMC
9031675 PubMed citation Europe PMC
Last Modified
10 January 2019