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CHEBI:142842 - andrastin A

ChEBI IDCHEBI:142842
ChEBI Nameandrastin A
Stars
DefinitionA 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.
Last Modified6 November 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC28H38O7
Net Charge0
Average Mass486.605
Monoisotopic Mass486.26175
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=O
InChIInChI=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
InChIKeySNSSSENJBPCLPM-OXILWVMOSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Penicillium roqueforti (ncbitaxon:5082)
- PubMed (19837474)
- PubMed (15826038)
Penicillium albocoremium (ncbitaxon:74831) - PubMed (16279417)
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:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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-carboxylateIUPAC
Manual XrefsDatabases
Andrastin_AWikipedia
Registry NumbersSources
CAS:174232-42-9ChEBI
Citations