2.02012-05-31 13:00:38 -06002015-10-15 16:13:47 -0600ECMDB00707M2MDB0001764-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.(p-hydroxyphenyl)-Pyruvate(p-hydroxyphenyl)-Pyruvic acid(p-Hydroxyphenyl)pyruvate(p-Hydroxyphenyl)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-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-Hydroxyphenylpyruvate4-Hydroxyphenylpyruvic acid4HPPA<i>p</i>-hydroxyphenylpyruvateHPPHPPAHydroxyphenylpyruvateHydroxyphenylpyruvic acidP-HydroxyphenylpyruvateP-HydroxyphenylpyruvicP-Hydroxyphenylpyruvic acidTestacidC9H8O4180.1574180.0422587443-(4-hydroxyphenyl)-2-oxopropanoic acid4-hydroxyphenylpyruvic acid156-39-8OC(=O)C(=O)CC1=CC=C(O)C=C1InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)KKADPXVIOXHVKN-UHFFFAOYSA-NSolidCytosollogp1.12logs-2.08solubility1.49e+00 g/lmelting_point219-220 oClogp1.6pka_strongest_acidic2.91pka_strongest_basic-6iupac3-(4-hydroxyphenyl)-2-oxopropanoic acidaverage_mass180.1574mono_mass180.042258744smilesOC(=O)C(=O)CC1=CC=C(O)C=C1formulaC9H8O4inchiInChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)inchikeyKKADPXVIOXHVKN-UHFFFAOYSA-Npolar_surface_area74.6refractivity44.69polarizability16.75rotatable_bond_count3acceptor_count4donor_count2physiological_charge-1formal_charge0Tyrosine metabolismec00350Phenylalanine, tyrosine and tryptophan biosynthesisec00400Novobiocin biosynthesisec00401Methane metabolismec00680Ubiquinone and other terpenoid-quinone biosynthesisec00130tyrosine biosynthesis ITYRSYNSpecdb::CMs618Specdb::CMs619Specdb::CMs1524Specdb::CMs1628Specdb::CMs1690Specdb::CMs1718Specdb::CMs2896Specdb::CMs30095Specdb::CMs30454Specdb::CMs30811Specdb::CMs31199Specdb::CMs31200Specdb::CMs31201Specdb::CMs31202Specdb::CMs31845Specdb::CMs31846Specdb::CMs37707Specdb::CMs156073Specdb::CMs1072545Specdb::CMs1072547Specdb::CMs1072549Specdb::CMs1072551Specdb::CMs1072552Specdb::CMs1072554Specdb::CMs1072556Specdb::EiMs845Specdb::NmrOneD1492Specdb::NmrOneD4999Specdb::NmrOneD5000Specdb::MsMs990Specdb::MsMs991Specdb::MsMs992Specdb::MsMs4481Specdb::MsMs4482Specdb::MsMs4483Specdb::MsMs4484Specdb::MsMs4485Specdb::MsMs9803Specdb::MsMs9804Specdb::MsMs9805Specdb::MsMs16475Specdb::MsMs16476Specdb::MsMs16477Specdb::MsMs437781Specdb::MsMs437782Specdb::MsMs437783Specdb::MsMs437784Specdb::MsMs437785Specdb::MsMs451975Specdb::MsMs2252675Specdb::MsMs2253795Specdb::MsMs2254772Specdb::MsMs2255816Specdb::MsMs2256706Specdb::NmrTwoD1032Specdb::NmrTwoD1438HMDB0070797911596439C01179P-HYDROXY-PHENYLPYRUVATEHydroxyphenylpyruvic acidKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Billek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54. http://hmdb.ca/system/metabolites/msds/000/000/626/original/HMDB00707.pdf?1358462345Aspartate aminotransferaseP00509AAT_ECOLIaspChttp://ecmdb.ca/proteins/P00509.xmlAromatic-amino-acid aminotransferaseP04693TYRB_ECOLItyrBhttp://ecmdb.ca/proteins/P04693.xmlHistidinol-phosphate aminotransferaseP06986HIS8_ECOLIhisChttp://ecmdb.ca/proteins/P06986.xmlT-proteinP07023TYRA_ECOLItyrAhttp://ecmdb.ca/proteins/P07023.xmlalpha-Ketoglutarate + L-Tyrosine <> 4-Hydroxyphenylpyruvic acid + L-GlutamateR00734NAD + Prephenate > 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADHR01728PREPHENATEDEHYDROG-RXNPrephenate + NAD <> 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH + Hydrogen ionR01728L-Tyrosine + Oxoglutaric acid <> 4-Hydroxyphenylpyruvic acid + L-GlutamateTYRAMINOTRANS-RXN