1.0 2011-09-21 00:09:53 UTC 2019-11-26 03:21:01 UTC FDB022193 4-Hydroxyphenylpyruvic acid 4-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 acid 3-(4-HYDROXY-phenyl)pyruvate 3-(4-HYDROXY-phenyl)pyruvIC ACID 3-(4-hydroxyphenyl)-2-oxo-propanoate 3-(4-hydroxyphenyl)-2-oxo-propanoic acid 3-(4-Hydroxyphenyl)-2-oxopropionate 3-(4-Hydroxyphenyl)-2-oxopropionic acid 3-(4-Hydroxyphenyl)pyruvate 3-(4-Hydroxyphenyl)pyruvic acid 3-(P-Hydroxyphenyl)-2-oxopropanoate 3-(P-Hydroxyphenyl)-2-oxopropanoic acid 3-(p-Hydroxyphenyl)-2-oxopropionate 3-(p-Hydroxyphenyl)-2-oxopropionic acid 3-(p-Hydroxyphenyl)pyruvate 3-(p-Hydroxyphenyl)pyruvic acid 4-Hydroxy a-oxobenzenepropanoate 4-Hydroxy a-oxobenzenepropanoic acid 4-Hydroxy alpha-oxobenzenepropanoate 4-Hydroxy alpha-oxobenzenepropanoic acid 4-Hydroxy α-oxobenzenepropanoate 4-Hydroxy α-oxobenzenepropanoic acid 4-Hydroxy-a-oxobenzenepropanoate 4-Hydroxy-a-oxobenzenepropanoic acid 4-Hydroxy-alpha-oxobenzenepropanoate 4-Hydroxy-alpha-oxobenzenepropanoic acid 4-hydroxyphenylpyruvate 4HPPA Hydroxyphenylpyruvate Hydroxyphenylpyruvic acid P-Hydroxyphenylpyruvate p-hydroxyphenylpyruvic P-Hydroxyphenylpyruvic acid Testacid C9H8O4 180.1574 180.042258744 3-hydroxy-2-oxo-3-phenylpropanoic acid HPPA 156-39-8 OC(C(=O)C(O)=O)C1=CC=CC=C1 InChI=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 derivatives Organic compounds Benzenoids Benzene and substituted derivatives Phenylpyruvic acid derivatives Aromatic homomonocyclic compounds Acyloins Alpha-hydroxy ketones Alpha-keto acids and derivatives Aromatic alcohols Beta hydroxy acids and derivatives Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharides Organic oxides Phenylpropanoic acids Secondary alcohols 3-phenylpropanoic-acid Acyloin Alcohol Alpha-hydroxy ketone Alpha-keto acid Aromatic alcohol Aromatic homomonocyclic compound Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxy acid Keto acid Ketone Monocarboxylic acid or derivatives Monosaccharide Organic oxide Organic oxygen compound Organooxygen compound Phenylpyruvate Secondary alcohol Solid logp 0.43 ALOGPS logs -1.57 ALOGPS solubility 4.89e+00 g/l ALOGPS logp 1.19 ChemAxon pka_strongest_acidic 2.98 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 3-hydroxy-2-oxo-3-phenylpropanoic acid ChemAxon average_mass 180.1574 ChemAxon mono_mass 180.042258744 ChemAxon smiles OC(C(=O)C(O)=O)C1=CC=CC=C1 ChemAxon formula C9H8O4 ChemAxon inchi InChI=1S/C9H8O4/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7,10H,(H,12,13) ChemAxon inchikey ZHLWCBHWYUISFY-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 44.05 ChemAxon polarizability 16.64 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Phenylalanine and Tyrosine Metabolism SMP00008 map00360 Tyrosine Metabolism SMP00006 map00350 Specdb::CMs 3062 Specdb::MsMs 29558 Specdb::MsMs 29559 Specdb::MsMs 29560 Specdb::MsMs 36116 Specdb::MsMs 36117 Specdb::MsMs 36118 HMDB00707 ENO #<Reference:0x000055ce3193e860> #<Reference:0x000055ce3193e6a8> #<Reference:0x000055ce3193e4f0> #<Reference:0x000055ce3193e338> #<Reference:0x000055ce3193e180> #<Reference:0x000055ce3193dfc8> #<Reference:0x000055ce3193de10> #<Reference:0x000055ce3193dc58> Milk (Cow) Type 2 specific Aspartate aminotransferase, cytoplasmic P17174 GOT1 Aspartate aminotransferase, mitochondrial P00505 GOT2 Macrophage migration inhibitory factor P14174 MIF Tyrosine aminotransferase P17735 TAT