4-hydroxyphenylpyruvic acid (CHEBI:15999)

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ChEBI Name	4-hydroxyphenylpyruvic acid

ChEBI ID	CHEBI:15999

Definition	A 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group.

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

Secondary ChEBI IDs	CHEBI:20426, CHEBI:42422, CHEBI:1431

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

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Wikipedia	License
4-Hydroxyphenylpyruvic acid (4-HPPA) is an intermediate in the metabolism of the amino acid phenylalanine. The aromatic side chain of phenylalanine is hydroxylated by the enzyme phenylalanine hydroxylase to form tyrosine. The conversion from tyrosine to 4-HPPA is in turn catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. It is an intermediary compound in the biosynthesis of scytonemin.
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Formula

C9H8O4

Net Charge

Average Mass

180.159

Monoisotopic Mass

180.04226

InChI

InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)

InChIKey

KKADPXVIOXHVKN-UHFFFAOYSA-N

SMILES

OC(=O)C(=O)CC1=CC=C(O)C=C1

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):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

ChEBI Ontology
Outgoing	4-hydroxyphenylpyruvic acid (CHEBI:15999) has functional parent pyruvic acid (CHEBI:32816) 4-hydroxyphenylpyruvic acid (CHEBI:15999) has role human metabolite (CHEBI:77746) 4-hydroxyphenylpyruvic acid (CHEBI:15999) is a 2-oxo monocarboxylic acid (CHEBI:35910) 4-hydroxyphenylpyruvic acid (CHEBI:15999) is a phenols (CHEBI:33853) 4-hydroxyphenylpyruvic acid (CHEBI:15999) is conjugate acid of 3-(4-hydroxyphenyl)pyruvate (CHEBI:36242)

Incoming	4-hydroxyphenylpyruvic acid oxime (CHEBI:131385) has functional parent 4-hydroxyphenylpyruvic acid (CHEBI:15999) 3-(4-hydroxyphenyl)pyruvate (CHEBI:36242) is conjugate base of 4-hydroxyphenylpyruvic acid (CHEBI:15999)

IUPAC Name

3-(4-hydroxyphenyl)-2-oxopropanoic acid

Synonyms	Sources
(4-hydroxyphenyl)pyruvic acid	ChEBI
(p-hydroxyphenyl)pyruvic acid	NIST Chemistry WebBook
3-(4-HYDROXY-PHENYL)PYRUVIC ACID	PDBeChem
3-(4-hydroxyphenyl)pyruvic acid	ChEBI
3-(p-hydroxyphenyl)-2-oxopropanoic acid	NIST Chemistry WebBook
4-hydroxy α-oxobenzenepropanoic acid	ChemIDplus
4-hydroxyphenylpyruvic acid	ChEBI
p-Hydroxyphenylpyruvic acid	KEGG COMPOUND

Last Modified

26 March 2021