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

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

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ChEBI ID	CHEBI:132128
ChEBI Name	(3R)-farnesyl-6-hydroxy-2,3,5-trimethyl-4-oxocyclohexa-1,5-diene-1-carboxylic acid
Stars
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.
Last Modified	7 January 2019
Submitter	Steve
Downloads	Molfile

Formula	C25H36O4
Net Charge	0
Average Mass	400.559
Monoisotopic Mass	400.26136
SMILES	CC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]1(C)C(=O)C(C)=C(O)C(C(=O)O)=C1C
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

Species of Metabolite	Component	Source	Comments
Aspergillus terreus NIH2624 (ncbitaxon:341663)	-	PubMed (25671343)	Strain: NIH2624

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:	Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .

ChEBI Ontology

Outgoing Relation(s)
	(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 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 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 conjugate acid of (3R)-farnesyl-2,3,5-trimethyl-6-oxido-4-oxocyclohexa-1,5-diene-1-carboxylate (CHEBI:131857)
Incoming Relation(s)
Incoming Relation(s)	(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