CHEBI:142842 - andrastin A

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ChEBI Name andrastin A
ChEBI ID CHEBI:142842
Definition A 19-oxo steroid that is that is andrastin B in which the hydroxy group at position 19 has been oxidised to give the corresponding aldehyde. 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.
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Formula C28H38O7
Net Charge 0
Average Mass 486.598
Monoisotopic Mass 486.26175
InChI InChI=1S/C28H38O7/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/h13-14,18-20,32H,9-12H2,1-8H3/t18-,19-,20+,25+,26+,27+,28-/m1/s1
InChIKey SNSSSENJBPCLPM-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])C=O)[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 roqueforti (NCBI:txid5082) See: PubMed
Penicillium simplicissimum (NCBI:txid69488) of strain FO-3929 See: PubMed
Penicillium albocoremium (NCBI:txid74831) 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 A (CHEBI:142842) has functional parent andrastin B (CHEBI:142862)
andrastin A (CHEBI:142842) has role Penicillium metabolite (CHEBI:76964)
andrastin A (CHEBI:142842) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
andrastin A (CHEBI:142842) is a 15-hydroxy steroid (CHEBI:38089)
andrastin A (CHEBI:142842) is a 17-oxo steroid (CHEBI:19168)
andrastin A (CHEBI:142842) is a 19-oxo steroid (CHEBI:38149)
andrastin A (CHEBI:142842) is a 5β steroid (CHEBI:136889)
andrastin A (CHEBI:142842) is a acetate ester (CHEBI:47622)
andrastin A (CHEBI:142842) is a enol (CHEBI:33823)
andrastin A (CHEBI:142842) is a meroterpenoid (CHEBI:64419)
andrastin A (CHEBI:142842) is a methyl ester (CHEBI:25248)
andrastin A (CHEBI:142842) is a steroid aldehyde (CHEBI:131565)
andrastin A (CHEBI:142842) is conjugate acid of andrastin A(1−) (CHEBI:142823)
Incoming andrastin A(1−) (CHEBI:142823) is conjugate base of andrastin A (CHEBI:142842)
IUPAC Name
methyl 3β-acetoxy-15-hydroxy-4,4,8α,12,16-pentamethyl-17,19-dioxo-5β,9β,10α,13α-androsta-11,15-diene-14-carboxylate
Synonym Source
methyl (3β,5β,8α,9β,10α,13α)-3-acetoxy-15-hydroxy-4,4,8,12,16-pentamethyl-17,19-dioxoandrosta-11,15-diene-14-carboxylate IUPAC
Manual Xref Database
Andrastin_A Wikipedia
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Registry Number Type Source
174232-42-9 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
16279417 PubMed citation Europe PMC
19837474 PubMed citation Europe PMC
26731665 PubMed citation Europe PMC
28529508 PubMed citation Europe PMC
28799296 PubMed citation Europe PMC
29270163 PubMed citation Europe PMC
29853169 PubMed citation Europe PMC
8682716 PubMed citation Europe PMC
8682717 PubMed citation Europe PMC
9531989 PubMed citation Europe PMC
Last Modified
06 November 2019