CHEBI:142862 - andrastin B

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ChEBI Name andrastin B
ChEBI ID CHEBI:142862
Definition A 17-oxo steroid that is andrastin C in which a hydrogen of the methyl group at position 19 has been replaced by a hydroxy group. 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 C28H40O7
Net Charge 0
Average Mass 488.614
Monoisotopic Mass 488.27740
InChI InChI=1S/C28H40O7/c1-15-13-19-25(6,28(23(33)34-8)22(32)16(2)21(31)26(15,28)7)11-9-18-24(4,5)20(35-17(3)30)10-12-27(18,19)14-29/h13,18-20,29,32H,9-12,14H2,1-8H3/t18-,19-,20+,25+,26+,27+,28-/m1/s1
InChIKey HWVZMVZNLKRRLT-OXILWVMOSA-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])CO)[H])(C)C)OC(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 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 B (CHEBI:142862) has functional parent andrastin C (CHEBI:142867)
andrastin B (CHEBI:142862) has role Penicillium metabolite (CHEBI:76964)
andrastin B (CHEBI:142862) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
andrastin B (CHEBI:142862) is a 15-hydroxy steroid (CHEBI:38089)
andrastin B (CHEBI:142862) is a 17-oxo steroid (CHEBI:19168)
andrastin B (CHEBI:142862) is a 19-hydroxy steroid (CHEBI:36842)
andrastin B (CHEBI:142862) is a 5β steroid (CHEBI:136889)
andrastin B (CHEBI:142862) is a acetate ester (CHEBI:47622)
andrastin B (CHEBI:142862) is a enol (CHEBI:33823)
andrastin B (CHEBI:142862) is a meroterpenoid (CHEBI:64419)
andrastin B (CHEBI:142862) is a methyl ester (CHEBI:25248)
andrastin B (CHEBI:142862) is a primary alcohol (CHEBI:15734)
andrastin B (CHEBI:142862) is conjugate acid of andrastin B(1−) (CHEBI:142822)
Incoming andrastin A (CHEBI:142842) has functional parent andrastin B (CHEBI:142862)
andrastin B(1−) (CHEBI:142822) is conjugate base of andrastin B (CHEBI:142862)
IUPAC Name
methyl 3β-(acetyloxy)-15,19-dihydroxy-4,4,8,12,16-pentamethyl-17-oxo-5β,8α,9β,10α,13α-androsta-11,15-diene-14-carboxylate
Synonym Source
methyl (3β,5β,8α,9β,10α,13α)-3-(acetyloxy)-15,19-dihydroxy-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
8682716 PubMed citation Europe PMC
8682717 PubMed citation Europe PMC
Last Modified
09 January 2019