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CHEBI:142862 - andrastin B

ChEBI IDCHEBI:142862
ChEBI Nameandrastin B
Stars
DefinitionA 17-oxo steroid that is andrastin C in which a hydrogen of the methyl group at position 19 has been replaced by a hydroxy group.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.
Last Modified9 January 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC28H40O7
Net Charge0
Average Mass488.621
Monoisotopic Mass488.27740
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@@]21CO
InChIInChI=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
InChIKeyHWVZMVZNLKRRLT-OXILWVMOSA-N
Species of MetaboliteComponentSourceComments
Penicillium roqueforti (ncbitaxon:5082) - PubMed (15826038)
Penicillium simplicissimum (ncbitaxon:69488) - PubMed (8682716) Strain: FO-3929
Penicillium camponotum (ncbitaxon:2072477) - PubMed (27616792)
Penicillium cataractarum (ncbitaxon:2100454) - PubMed (27616792)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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-carboxylateIUPAC
Citations