prephenic acid (CHEBI:16666)

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ChEBI Name	prephenic acid

ChEBI ID	CHEBI:16666

Definition	An oxo dicarboxylic acid that consists of 4-hydroxycyclohexa-2,5-diene-1-carboxylic acid substituted by a 2-carboxy-2-oxoethyl group at position 1.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45028, CHEBI:8399, CHEBI:26257

Supplier Information	ChemicalBook:CB81303953

Download	Molfile XML SDF

Wikipedia	License
Prephenic acid, commonly also known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine, as well as of a large number of secondary metabolites of the shikimate pathway.
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Formula

C10H10O6

Net Charge

Average Mass

226.18280

Monoisotopic Mass

226.04774

InChI

InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)

InChIKey

FPWMCUPFBRFMLH-UHFFFAOYSA-N

SMILES

OC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O

Metabolite of Species	Details
Escherichia coli (NCBI:txid562)	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):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.

ChEBI Ontology
Outgoing	prephenic acid (CHEBI:16666) has role Escherichia coli metabolite (CHEBI:76971) prephenic acid (CHEBI:16666) has role plant metabolite (CHEBI:76924) prephenic acid (CHEBI:16666) is a oxo dicarboxylic acid (CHEBI:36145) prephenic acid (CHEBI:16666) is conjugate acid of (1s,4s)-prephenate(2−) (CHEBI:29934) prephenic acid (CHEBI:16666) is conjugate acid of prephenate(2−) (CHEBI:57852)

Incoming	(1s,4s)-prephenic acid (CHEBI:84387) is a prephenic acid (CHEBI:16666) (1s,4s)-prephenate(2−) (CHEBI:29934) is conjugate base of prephenic acid (CHEBI:16666) prephenate(2−) (CHEBI:57852) is conjugate base of prephenic acid (CHEBI:16666)

Synonyms	Sources
1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid	ChemIDplus
1-carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid	ChemIDplus
Prephenic acid	KEGG COMPOUND
PREPHENIC ACID	PDBeChem

Citations

Last Modified

16 July 2015