andrastin D (CHEBI:142874)

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CHEBI:142874 - andrastin D

ChEBI ID	CHEBI:142874
ChEBI Name	andrastin D
Stars
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.
Last Modified	10 January 2019
Submitter	Gareth Owen
Downloads	Molfile

Formula	C26H36O5
Net Charge	0
Average Mass	428.569
Monoisotopic Mass	428.25627
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(=O)CC[C@@]21C
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

Species of Metabolite	Component	Source	Comments
Penicillium roqueforti (ncbitaxon:5082)
	-	PubMed (15826038)
	-	PubMed (19837474)
Penicillium simplicissimum (ncbitaxon:69488)	-	PubMed (9031675)	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 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 Relation(s)
	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 Xrefs	Databases
C00016286	KNApSAcK

Registry Numbers	Sources
CAS:184432-08-4	KNApSAcK

Citations