1.02011-09-21 00:09:53 UTC2019-11-26 03:21:01 UTCFDB0221934-Hydroxyphenylpyruvic acid4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase [EC 1.1.1.222] and is formed during tyrosine metabolism (KEGG). There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction of 4-hydroxyphenylpyruvic acid to homogentisic acid in the tyrosine catabolism pathway. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718). [HMDB](p-hydroxyphenyl)-Pyruvate(p-hydroxyphenyl)-Pyruvic acid(p-Hydroxyphenyl)pyruvate(p-Hydroxyphenyl)pyruvic acid3-(4-HYDROXY-phenyl)pyruvate3-(4-HYDROXY-phenyl)pyruvIC ACID3-(4-hydroxyphenyl)-2-oxo-propanoate3-(4-hydroxyphenyl)-2-oxo-propanoic acid3-(4-Hydroxyphenyl)-2-oxopropionate3-(4-Hydroxyphenyl)-2-oxopropionic acid3-(4-Hydroxyphenyl)pyruvate3-(4-Hydroxyphenyl)pyruvic acid3-(P-Hydroxyphenyl)-2-oxopropanoate3-(P-Hydroxyphenyl)-2-oxopropanoic acid3-(p-Hydroxyphenyl)-2-oxopropionate3-(p-Hydroxyphenyl)-2-oxopropionic acid3-(p-Hydroxyphenyl)pyruvate3-(p-Hydroxyphenyl)pyruvic acid4-Hydroxy a-oxobenzenepropanoate4-Hydroxy a-oxobenzenepropanoic acid4-Hydroxy alpha-oxobenzenepropanoate4-Hydroxy alpha-oxobenzenepropanoic acid4-Hydroxy α-oxobenzenepropanoate4-Hydroxy α-oxobenzenepropanoic acid4-Hydroxy-a-oxobenzenepropanoate4-Hydroxy-a-oxobenzenepropanoic acid4-Hydroxy-alpha-oxobenzenepropanoate4-Hydroxy-alpha-oxobenzenepropanoic acid4-hydroxyphenylpyruvate4HPPAHydroxyphenylpyruvateHydroxyphenylpyruvic acidP-Hydroxyphenylpyruvatep-hydroxyphenylpyruvicP-Hydroxyphenylpyruvic acidTestacidC9H8O4180.1574180.0422587443-hydroxy-2-oxo-3-phenylpropanoic acidHPPA156-39-8OC(C(=O)C(O)=O)C1=CC=CC=C1InChI=1S/C9H8O4/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7,10H,(H,12,13)ZHLWCBHWYUISFY-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.Phenylpyruvic acid derivativesOrganic compoundsBenzenoidsBenzene and substituted derivativesPhenylpyruvic acid derivativesAromatic homomonocyclic compoundsAcyloinsAlpha-hydroxy ketonesAlpha-keto acids and derivativesAromatic alcoholsBeta hydroxy acids and derivativesCarboxylic acidsHydrocarbon derivativesMonocarboxylic acids and derivativesMonosaccharidesOrganic oxidesPhenylpropanoic acidsSecondary alcohols3-phenylpropanoic-acidAcyloinAlcoholAlpha-hydroxy ketoneAlpha-keto acidAromatic alcoholAromatic homomonocyclic compoundBeta-hydroxy acidCarbonyl groupCarboxylic acidCarboxylic acid derivativeHydrocarbon derivativeHydroxy acidKeto acidKetoneMonocarboxylic acid or derivativesMonosaccharideOrganic oxideOrganic oxygen compoundOrganooxygen compoundPhenylpyruvateSecondary alcoholSolidlogp0.43logs-1.57solubility4.89e+00 g/llogp1.19pka_strongest_acidic2.98pka_strongest_basic-3.9iupac3-hydroxy-2-oxo-3-phenylpropanoic acidaverage_mass180.1574mono_mass180.042258744smilesOC(C(=O)C(O)=O)C1=CC=CC=C1formulaC9H8O4inchiInChI=1S/C9H8O4/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7,10H,(H,12,13)inchikeyZHLWCBHWYUISFY-UHFFFAOYSA-Npolar_surface_area74.6refractivity44.05polarizability16.64rotatable_bond_count3acceptor_count4donor_count2physiological_charge-1formal_charge0Phenylalanine and Tyrosine MetabolismSMP00008map00360Tyrosine MetabolismSMP00006map00350Specdb::CMs3062Specdb::MsMs29558Specdb::MsMs29559Specdb::MsMs29560Specdb::MsMs36116Specdb::MsMs36117Specdb::MsMs36118HMDB00707ENO#<Reference:0x0000555675574718>#<Reference:0x0000555675574538>#<Reference:0x00005556755742e0>#<Reference:0x00005556755740b0>#<Reference:0x0000555675573ef8>#<Reference:0x0000555675573d18>#<Reference:0x0000555675573a48>#<Reference:0x0000555675573868>Milk (Cow)Type 2specificAspartate aminotransferase, cytoplasmicP17174GOT1Aspartate aminotransferase, mitochondrialP00505GOT2Macrophage migration inhibitory factorP14174MIFTyrosine aminotransferaseP17735TAT