4-Hydroxyphenylpyruvic acid

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4-Hydroxyphenylpyruvic acid

IUPAC name 3-(4-hydroxyphenyl)-2-oxo-propanoic acid
Identifiers
CAS number	156-39-8
PubChem	979
ChemSpider	954^Y
DrugBank	DB07718
KEGG	C01179^Y
ChEBI	CHEBI:15999^Y
ChEMBL	CHEMBL607712^Y
Jmol-3D images	Image 1
SMILES O=C(O)C(=O)Cc1ccc(O)cc1
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)^Y Key: KKADPXVIOXHVKN-UHFFFAOYSA-N^Y InChI=1/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13) Key: KKADPXVIOXHVKN-UHFFFAOYAH
Properties
Molecular formula	C₉H₈O₄
Molar mass	180.157 g/mol
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[1] Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment.^[2]

References

^ Brand, Larry; Harper, Alfred (1974). "Effect of glucagon on phenylalanine metabolism and phenylalanine-degrading enzymes in the rat". Biochemical Journal 142 (2): 231–45. PMC 1168273. PMID 4155291. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1168273.
^ Denoya, Claudio; Skinner, Deborah; Morgenstern, Margaret (September 1994). Journal of Bacteriology 1 (17): 5312–5319. http://jb.asm.org/cgi/reprint/176/17/5312. Retrieved 18 July 2011.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

G→pyruvate→citrate

glycine→serine→

3-Phosphoglyceric acid

glycine→creatine: Glycocyamine · Phosphocreatine · Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid · Imidazol-4-one-5-propionic acid · Formiminoglutamic acid · Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Ornithine · Putrescine · Agmatine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

G→fumarate


phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid · Homogentisic acid · 4-Maleylacetoacetate

G→oxaloacetate

see urea cycle

Other


Cysteine metabolism	Cysteine sulfinic acid

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

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