Phenylpyruvic acid (PAMDB000084)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000084
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
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 164.158
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as phenylpyruvic acid derivatives. These 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 ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct Parent Phenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Phenylpyruvate
  • 3-phenylpropanoic-acid
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 154
Experimental Properties:
PropertyValueSource
Water Solubility:112 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.932 mg/mLALOGPS
logP1.3ALOGPS
logP1.9ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.71 m3·mol-1ChemAxon
Polarizability15.75 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + 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
Hydrogen ion + 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
Pathways:
  • Phenylalanine metabolism pae00360
  • Phenylalanine, tyrosine and tryptophan biosynthesis pae00400
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00ko-9700000000-1a891469df1de787159bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0006-1900000000-7dc1a5344d13e4dc19acView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001i-0900000000-bbbc84c54d03c4a14e51View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4i-0900000000-00b547b0371603520b61View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX)splash10-00di-9100000000-fdd48b632e63c8478078View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000f-9300000000-8cd32f87e04ae0b6d6fbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-014u-9720000000-7a0b66e6c18ff42ac05eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0006-9760000000-d94111a7b9babceb265bView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-066r-0900000000-ceb2ce23352e0f45ee33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9200000000-ed4a6740d574858da982View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-c239a9a599daa607e47fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00kf-9300000000-d1a7d23e7c5270b16883View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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)
External Links:
ResourceLink
CHEBI ID18005
HMDB IDHMDB00205
Pubchem Compound ID997
Kegg IDC00166
ChemSpider ID972
Wikipedia IDNot Available
BioCyc IDPHENYL-PYRUVATE
EcoCyc IDPHENYL-PYRUVATE
Ligand ExpoPPY