CHEBI:132128 - (3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid

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ChEBI Name (3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid
ChEBI ID CHEBI:132128
ChEBI ASCII Name (3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid
Definition A sesterterpenoid that is 4-oxocyclohexa-1,5-diene-1-carboxylic acid carrying three additional methyl substituents at positions 2, 3 and 5 as well as farnsyl and hydroxy substituents at positions 3 and 6 respectively. An intermediate in the biosynthesis of terretonin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000535385293
Download Molfile XML SDF
Formula C25H36O4
Net Charge 0
Average Mass 400.552
Monoisotopic Mass 400.26136
InChI InChI=1S/C25H36O4/c1-16(2)10-8-11-17(3)12-9-13-18(4)14-15-25(7)20(6)21(24(28)29)22(26)19(5)23(25)27/h10,12,14,26H,8-9,11,13,15H2,1-7H3,(H,28,29)/b17-12+,18-14+/t25-/m1/s1
InChIKey BAJLPQKQXYOBIY-MNPZXIHOSA-N
SMILES C1([C@@](C(=C(C(=C1C)O)C(=O)O)C)(C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)C)=O
Metabolite of Species Details
Aspergillus terreus NIH2624 (NCBI:txid341663) of strain NIH2624 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) has role Aspergillus metabolite (CHEBI:76956)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is a 3-hydroxy monocarboxylic acid (CHEBI:35969)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is a 5-oxo monocarboxylic acid (CHEBI:35952)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is a cyclic terpene ketone (CHEBI:36130)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is a enol (CHEBI:33823)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is a enone (CHEBI:51689)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is a sesterterpenoid (CHEBI:26660)
(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128) is conjugate acid of (3R)-farnesyl-2,3,5-trimethyl-6-oxido-4-oxocyclohexa-1,5-diene-1-carboxylate (CHEBI:131857)
Incoming (3R)-farnesyl-2,3,5-trimethyl-6-oxido-4-oxocyclohexa-1,5-diene-1-carboxylate (CHEBI:131857) is conjugate base of (3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid (CHEBI:132128)
IUPAC Name
(3R)-6-hydroxy-2,3,5-trimethyl-4-oxo-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]cyclohexa-1,5-diene-1-carboxylic acid
Citations
Matsuda Y, Awakawa T, Itoh T, Wakimoto T, Kushiro T, Fujii I, Ebizuka Y, Abe I (2012)
Terretonin biosynthesis requires methylation as essential step for cyclization.
Chembiochem : a European journal of chemical biology 13, 1738-1741 [PubMed:22782788]
Guo CJ, Knox BP, Chiang YM, Lo HC, Sanchez JF, Lee KH, Oakley BR, Bruno KS, Wang CC (2012)
Molecular genetic characterization of a cluster in A. terreus for biosynthesis of the meroterpenoid terretonin.
Organic letters 14, 5684-5687 [PubMed:23116177]
[show Abstract]
Last Modified
07 January 2019