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Record Information
Version	2.0
Creation Date	2012-05-31 10:23:39 -0600
Update Date	2015-09-13 12:56:06 -0600
Secondary Accession Numbers	ECMDB00205
Identification
Name:	Phenylpyruvic acid
Description	Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Phenylalanine is converted to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa8c1fa90> Close
Synonyms:	α-ketohydrocinnamate α-ketohydrocinnamic acid 2-Keto-phenyl-pyruvate 2-Keto-phenyl-pyruvic acid 2-Oxo-3-phenylpropanoate 2-Oxo-3-phenylpropanoic acid 3-Phenyl-2-oxopropanoate 3-Phenyl-2-oxopropanoic acid 3-Phenylpyruvate 3-Phenylpyruvic acid a-Ketohydrocinnamate a-Ketohydrocinnamic acid Alpha-Ketohydrocinnamate Alpha-Ketohydrocinnamic acid B-Phenylpyruvate B-Phenylpyruvic acid Beta-Phenylpyruvate Beta-Phenylpyruvic acid Keto-Phenylpyruvate Keto-Phenylpyruvic acid Phenylpyroracemate Phenylpyroracemic acid Phenylpyruvate α-Ketohydrocinnamate α-Ketohydrocinnamic acid β-Phenylpyruvate β-Phenylpyruvic acid
Chemical Formula:	C9H8O3
Weight:	Average: 164.158 Monoisotopic: 164.047344122
InChI Key:	BTNMPGBKDVTSJY-UHFFFAOYSA-N
InChI:	InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
CAS number:	156-06-9
IUPAC Name:	2-oxo-3-phenylpropanoic acid
Traditional IUPAC Name:	phenylpyruvic acid
SMILES:	OC(=O)C(=O)CC1=CC=CC=C1
Chemical Taxonomy
Description	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.
Kingdom	Organic compounds
Super Class	Benzenoids
Class	Benzene and substituted derivatives
Sub Class	Phenylpyruvic acid derivatives
Direct Parent	Phenylpyruvic acid derivatives
Alternative Parents	Phenylpropanoic acids Alpha-keto acids and derivatives Alpha-hydroxy ketones Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Phenylpyruvate 3-phenylpropanoic-acid Keto acid Alpha-keto acid Alpha-hydroxy ketone Ketone Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	2-oxo monocarboxylic acid (CHEBI:30851 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	154
Experimental Properties:	Property Value Source Water Solubility: 112 mg/mL [HMP experimental] PhysProp
Predicted Properties	Property Value Source logP 1.9 ChemAxon pKa (Strongest Acidic) 3.33 ChemAxon pKa (Strongest Basic) -9.8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 54.37 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 42.71 m³·mol⁻¹ ChemAxon Polarizability 15.75 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid Hydrogen ion + Prephenate > Carbon dioxide + Water + Phenylpyruvic acid Prephenate <> Phenylpyruvic acid + Water + Carbon dioxide D-Phenylalanine + Water + Acceptor <> Phenylpyruvic acid + Ammonia + Reduced acceptor Phenylpyruvic acid + L-Glutamate <> L-Phenylalanine + Oxoglutaric acid Prephenate > Phenylpyruvic acid + Water + Carbon dioxide Phenylpyruvic acid + Ammonia + cytochrome c nitrite reductase <> D-Phenylalanine + Water + cytochrome c nitrite reductase Phenylpyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Phenylalanine + L-Phenylalanine L-Phenylalanine + Oxygen + L-Phenylalanine <> Oxoglutaric acid + Phenylpyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid Hydrogen ion + Prephenate > Carbon dioxide + Water + Phenylpyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid
SMPDB Pathways:	Phenylalanine metabolism PW000921 phenylalanine biosynthesis PW000807
KEGG Pathways:	Phenylalanine metabolism ec00360 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:	phenylalanine biosynthesis I PHESYN
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 90± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 195± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 148± 0 uM K12 NCM3722 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) splash10-00ko-9700000000-1a891469df1de787159b View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0006-1900000000-7dc1a5344d13e4dc19ac View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-001i-0900000000-bbbc84c54d03c4a14e51 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0a4i-0900000000-00b547b0371603520b61 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX) splash10-00di-9100000000-fdd48b632e63c8478078 View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) splash10-000f-9300000000-8cd32f87e04ae0b6d6fb View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) splash10-014u-9720000000-7a0b66e6c18ff42ac05e View in MoNA GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-0006-9760000000-d94111a7b9babceb265b View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00ko-9700000000-1a891469df1de787159b View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00di-9100000000-fdd48b632e63c8478078 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-000f-9300000000-8cd32f87e04ae0b6d6fb View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-014u-9720000000-7a0b66e6c18ff42ac05e View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0006-9760000000-d94111a7b9babceb265b View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-000f-9300000000-8cd32f87e04ae0b6d6fb View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-014u-9720000000-7a0b66e6c18ff42ac05e View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0006-9760000000-d94111a7b9babceb265b View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00ko-9700000000-cec4a53271b8d66c2abc View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9300000000-9a8a36c751256480752e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-00r6-9500000000-3e83cb905f1fd4362497 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-066r-0900000000-ceb2ce23352e0f45ee33 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-004i-9200000000-ed4a6740d574858da982 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-004i-9000000000-c239a9a599daa607e47f View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QFT , negative splash10-014i-0900000000-36e00f6baa5d907e851b View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative splash10-014i-0900000000-843a66173124c8fdf184 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Negative splash10-014i-0900000000-272f6079d347e1b34e86 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014j-1900000000-5d025096b1bb0e80dc1c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014m-3900000000-9d0be907ecb6cc5efe8c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9200000000-a4fc563b3536eafc044d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-1900000000-0f660ae6dc074d939404 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-014j-1900000000-d229883bf098b04e0fcb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014i-5900000000-a107b725b71a6441a80c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03xr-1900000000-8ba05dd4c5612aae9f50 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-9300000000-946fa61c2a2596d7592d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9200000000-fa13a9bfbb6c03b2e12d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014l-4900000000-2d56731d3ebcebf8079a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-9200000000-9b3ae8fbf3992b1b2f28 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9000000000-089373761153dce3ca74 View in MoNA MS Mass Spectrum (Electron Ionization) splash10-00kf-9300000000-d1a7d23e7c5270b16883 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621 Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. Pubmed: 14708889 Cassidei L, Dell'atti A, Sciacovelli O: Improvement of the FeCl3 test for phenylpyruvic acid. Clin Chim Acta. 1978 Dec 1;90(2):121-7. Pubmed: 719897 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. Pubmed: 22080510 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. Pubmed: 21097882 Lasala JM, Coscia CJ: Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science. 1979 Jan 19;203(4377):283-4. Pubmed: 153583 Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. Pubmed: 9869358 Michals K, Matalon R: Phenylalanine metabolites, attention span and hyperactivity. Am J Clin Nutr. 1985 Aug;42(2):361-5. Pubmed: 4025205 Nakahara T, Ishida J, Yamaguchi M, Nakamura M: Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection. Anal Biochem. 1990 Nov 1;190(2):309-13. Pubmed: 2291475 Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685 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. Pubmed: 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. Pubmed: 18331064 Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Synthesis Reference:	Li, Hongbin; Luo, Yuzhong. Preparation of phenyl-pyruvic acid by dicarbonylation of benzyl halide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1996), 5 pp.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 18005 HMDB ID HMDB00205 Pubchem Compound ID 997 Kegg ID C00166 ChemSpider ID 972 Wikipedia ID Phenylpyruvic_acid BioCyc ID PHENYL-PYRUVATE EcoCyc ID PHENYL-PYRUVATE Ligand Expo PPY

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