Record Information
Version1.0
Creation Date2016-09-30 22:26:40 UTC
Update Date2020-06-04 19:47:16 UTC
BMDB IDBMDB0000205
Secondary Accession Numbers
  • BMDB00205
Metabolite Identification
Common NamePhenylpyruvic acid
DescriptionPhenylpyruvic acid, also known as keto-phenylpyruvate or a-ketohydrocinnamate, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylpyruvic acid exists in all living species, ranging from bacteria to humans. Within cattle, phenylpyruvic acid participates in a number of enzymatic reactions. In particular, phenylpyruvic acid and L-glutamic acid can be biosynthesized from L-phenylalanine and oxoglutaric acid; which is mediated by the enzyme aspartate aminotransferase, cytoplasmic. In addition, phenylpyruvic acid can be biosynthesized from L-phenylalanine through the action of the enzyme L-amino-acid oxidase. In cattle, phenylpyruvic acid is involved in the metabolic pathway called the phenylalanine and tyrosine metabolism pathway. Phenylpyruvic acid is a potentially toxic compound. Phenylpyruvic acid, with regard to humans, has been found to be associated with the diseases such as primary biliary cirrhosis; phenylpyruvic acid has also been linked to the inborn metabolic disorder phenylketonuria.
Structure
Thumb
Synonyms
ValueSource
3-Phenyl-2-oxopropanoateChEBI
3-Phenyl-2-oxopropanoic acidChEBI
3-Phenylpyruvic acidChEBI
alpha-Ketohydrocinnamic acidChEBI
alpha-Oxo-benzenepropanoic acidChEBI
beta-Phenylpyruvic acidChEBI
Keto-phenylpyruvateChEBI
PhenylbrenztraubensaeureChEBI
PhenylpyruvateChEBI
3-PHENYLPYRUVateGenerator
a-KetohydrocinnamateGenerator
a-Ketohydrocinnamic acidGenerator
alpha-KetohydrocinnamateGenerator
α-KetohydrocinnamateGenerator
α-Ketohydrocinnamic acidGenerator
a-Oxo-benzenepropanoateGenerator
a-Oxo-benzenepropanoic acidGenerator
alpha-Oxo-benzenepropanoateGenerator
α-Oxo-benzenepropanoateGenerator
α-Oxo-benzenepropanoic acidGenerator
b-PhenylpyruvateGenerator
b-Phenylpyruvic acidGenerator
beta-PhenylpyruvateGenerator
β-PhenylpyruvateGenerator
β-Phenylpyruvic acidGenerator
keto-Phenylpyruvic acidGenerator
2-Oxo-3-phenylpropanoateHMDB, KEGG
2-Oxo-3-phenylpropanoic acidHMDB, Generator
a-Hydroxycinnamic acidHMDB
FEMA 3892HMDB
Phenylpyruvic acidChEBI
2-Oxo-3-phenylpropionic acidHMDB
3-Phenyl-2-oxopropionic acidHMDB
alpha-Oxobenzenepropanoic acidHMDB
alpha-Oxobenzenepropionic acidHMDB
α-Oxobenzenepropanoic acidHMDB
α-Oxobenzenepropionic acidHMDB
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name2-oxo-3-phenylpropanoic acid
Traditional Namephenylpyruvic acid
CAS Registry Number156-06-9
SMILES
OC(=O)C(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
InChI KeyBTNMPGBKDVTSJY-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point154 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility112 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.9ChemAxon
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.71 m³·mol⁻¹ChemAxon
Polarizability15.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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) (Non-derivatized)splash10-0006-1900000000-7dc1a5344d13e4dc19acView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0900000000-bbbc84c54d03c4a14e51View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)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-EI-TOF (Non-derivatized)splash10-00ko-9700000000-1a891469df1de787159bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9100000000-fdd48b632e63c8478078View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000f-9300000000-8cd32f87e04ae0b6d6fbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014u-9720000000-7a0b66e6c18ff42ac05eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9760000000-d94111a7b9babceb265bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000f-9300000000-8cd32f87e04ae0b6d6fbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014u-9720000000-7a0b66e6c18ff42ac05eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9760000000-d94111a7b9babceb265bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ko-9700000000-cec4a53271b8d66c2abcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-9a8a36c751256480752eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-9500000000-3e83cb905f1fd4362497View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-36e00f6baa5d907e851bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-014i-0900000000-843a66173124c8fdf184View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-272f6079d347e1b34e86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-1900000000-5d025096b1bb0e80dc1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3900000000-9d0be907ecb6cc5efe8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-a4fc563b3536eafc044dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-0f660ae6dc074d939404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1900000000-d229883bf098b04e0fcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-a107b725b71a6441a80cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-1900000000-8ba05dd4c5612aae9f50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-946fa61c2a2596d7592dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-fa13a9bfbb6c03b2e12dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-4900000000-2d56731d3ebcebf8079aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-9b3ae8fbf3992b1b2f28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-089373761153dce3ca74View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-9300000000-d1a7d23e7c5270b16883View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified16.7 +/- 13.5 uMNot SpecifiedBothNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000205
DrugBank IDDB03884
Phenol Explorer Compound IDNot Available
FooDB IDFDB008272
KNApSAcK IDC00000751
Chemspider ID972
KEGG Compound IDC00166
BioCyc IDPHENYL-PYRUVATE
BiGG ID34111
Wikipedia LinkPhenylpyruvic_acid
METLIN ID328
PubChem Compound997
PDB IDNot Available
ChEBI ID30851
References
Synthesis ReferenceLi, 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)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cytokine activity
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity (By similarity).
Gene Name:
MIF
Uniprot ID:
P80177
Molecular weight:
12343.0
General function:
Amino acid transport and metabolism
Specific function:
Biosynthesis of L-glutamate from L-aspartate or L-cysteine. Important regulator of levels of glutamate, the major excitatory neurotransmitter of the vertebrate central nervous system. Acts as a scavenger of glutamate in brain neuroprotection. The aspartate aminotransferase activity is involved in hepatic glucose synthesis during development and in adipocyte glyceroneogenesis. Using L-cysteine as substrate, regulates levels of mercaptopyruvate, an important source of hydrogen sulfide. Mercaptopyruvate is converted into H(2)S via the action of 3-mercaptopyruvate sulfurtransferase (3MST). Hydrogen sulfide is an important synaptic modulator and neuroprotectant in the brain (By similarity).
Gene Name:
GOT1
Uniprot ID:
P33097
Molecular weight:
46399.0
Reactions
L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic aciddetails
General function:
Amino acid transport and metabolism
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity for phenylalanine (By similarity).
Gene Name:
TAT
Uniprot ID:
Q58CZ9
Molecular weight:
49691.0
Reactions
L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic aciddetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
IL4I1
Uniprot ID:
F1N191
Molecular weight:
64479.0
Reactions
L-Phenylalanine + Water + Oxygen → Phenylpyruvic acid + Ammonia + Hydrogen peroxidedetails