2.0 2012-05-31 13:00:38 -0600 2015-10-15 16:13:47 -0600 ECMDB00707 M2MDB000176 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. (p-hydroxyphenyl)-Pyruvate (p-hydroxyphenyl)-Pyruvic acid (p-Hydroxyphenyl)pyruvate (p-Hydroxyphenyl)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-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-Hydroxyphenylpyruvate 4-Hydroxyphenylpyruvic acid 4HPPA <i>p</i>-hydroxyphenylpyruvate HPP HPPA Hydroxyphenylpyruvate Hydroxyphenylpyruvic acid P-Hydroxyphenylpyruvate P-Hydroxyphenylpyruvic P-Hydroxyphenylpyruvic acid Testacid C9H8O4 180.1574 180.042258744 3-(4-hydroxyphenyl)-2-oxopropanoic acid 4-hydroxyphenylpyruvic acid 156-39-8 OC(=O)C(=O)CC1=CC=C(O)C=C1 InChI=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-N Solid Cytosol logp 1.12 ALOGPS logs -2.08 ALOGPS solubility 1.49e+00 g/l ALOGPS melting_point 219-220 oC logp 1.6 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -6 ChemAxon iupac 3-(4-hydroxyphenyl)-2-oxopropanoic acid ChemAxon average_mass 180.1574 ChemAxon mono_mass 180.042258744 ChemAxon smiles OC(=O)C(=O)CC1=CC=C(O)C=C1 ChemAxon formula C9H8O4 ChemAxon 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) ChemAxon inchikey KKADPXVIOXHVKN-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 44.69 ChemAxon polarizability 16.75 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Tyrosine metabolism ec00350 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Novobiocin biosynthesis ec00401 Methane metabolism ec00680 Ubiquinone and other terpenoid-quinone biosynthesis ec00130 tyrosine biosynthesis I TYRSYN Specdb::CMs 618 Specdb::CMs 619 Specdb::CMs 1524 Specdb::CMs 1628 Specdb::CMs 1690 Specdb::CMs 1718 Specdb::CMs 2896 Specdb::CMs 30095 Specdb::CMs 30454 Specdb::CMs 30811 Specdb::CMs 31199 Specdb::CMs 31200 Specdb::CMs 31201 Specdb::CMs 31202 Specdb::CMs 31845 Specdb::CMs 31846 Specdb::CMs 37707 Specdb::CMs 156073 Specdb::CMs 1072545 Specdb::CMs 1072547 Specdb::CMs 1072549 Specdb::CMs 1072551 Specdb::CMs 1072552 Specdb::CMs 1072554 Specdb::CMs 1072556 Specdb::EiMs 845 Specdb::NmrOneD 1492 Specdb::NmrOneD 4999 Specdb::NmrOneD 5000 Specdb::MsMs 990 Specdb::MsMs 991 Specdb::MsMs 992 Specdb::MsMs 4481 Specdb::MsMs 4482 Specdb::MsMs 4483 Specdb::MsMs 4484 Specdb::MsMs 4485 Specdb::MsMs 9803 Specdb::MsMs 9804 Specdb::MsMs 9805 Specdb::MsMs 16475 Specdb::MsMs 16476 Specdb::MsMs 16477 Specdb::MsMs 437781 Specdb::MsMs 437782 Specdb::MsMs 437783 Specdb::MsMs 437784 Specdb::MsMs 437785 Specdb::MsMs 451975 Specdb::MsMs 2252675 Specdb::MsMs 2253795 Specdb::MsMs 2254772 Specdb::MsMs 2255816 Specdb::MsMs 2256706 Specdb::NmrTwoD 1032 Specdb::NmrTwoD 1438 HMDB00707 979 11596439 C01179 P-HYDROXY-PHENYLPYRUVATE Hydroxyphenylpyruvic acid Keseler, 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. 21097882 Kanehisa, 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. 22080510 van 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. 17765195 Winder, 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. 18331064 Billek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54. http://hmdb.ca/system/metabolites/msds/000/000/626/original/HMDB00707.pdf?1358462345 Aspartate aminotransferase P00509 AAT_ECOLI aspC http://ecmdb.ca/proteins/P00509.xml Aromatic-amino-acid aminotransferase P04693 TYRB_ECOLI tyrB http://ecmdb.ca/proteins/P04693.xml Histidinol-phosphate aminotransferase P06986 HIS8_ECOLI hisC http://ecmdb.ca/proteins/P06986.xml T-protein P07023 TYRA_ECOLI tyrA http://ecmdb.ca/proteins/P07023.xml alpha-Ketoglutarate + L-Tyrosine <> 4-Hydroxyphenylpyruvic acid + L-Glutamate R00734 NAD + Prephenate > 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH R01728 PREPHENATEDEHYDROG-RXN Prephenate + NAD <> 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH + Hydrogen ion R01728 L-Tyrosine + Oxoglutaric acid <> 4-Hydroxyphenylpyruvic acid + L-Glutamate TYRAMINOTRANS-RXN