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Showing Compound 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) (FDB008272)

Record Information
Version1.0
Creation date2010-04-08 22:08:00 UTC
Update date2020-09-17 15:40:41 UTC
Primary IDFDB008272
Secondary Accession Numbers
  • FDB020197
Chemical Information
FooDB Name2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto)
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 humans, 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 humans, phenylpyruvic acid is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). 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. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. Metabolites of this transamination reaction include phenylacetate, Phenylpyruvic acid and phenethylamine. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed.
CAS Number156-06-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
2-Hydroxy-3-phenyl-2-propenoic acid, 9CIdb_source
2-oxo-3-PhenylpropanoateHMDB
3-PHENYLPYRUVIC ACIDChEBI
a-oxo-BenzenepropanoateGenerator
a-oxo-Benzenepropanoic acidGenerator
a-Oxobenzenepropanoic acid, 9CIdb_source
alpha-oxo-BenzenepropanoateGenerator
alpha-oxo-Benzenepropanoic acidChEBI
keto-PhenylpyruvateChEBI
PhenylpyroracemateHMDB
Phenylpyroracemic acidHMDB
α-ketohydrocinnamateGenerator
α-ketohydrocinnamic acidGenerator
α-oxo-benzenepropanoateGenerator
α-oxo-benzenepropanoic acidGenerator
β-phenylpyruvateGenerator
β-phenylpyruvic acidGenerator
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O3
IUPAC name2-oxo-3-phenylpropanoic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)C(=O)CC1=CC=CC=C1
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
Classification
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 65.85%; H 4.91%; O 29.24%DFC
Melting PointMp 157° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-9300000000-d1a7d23e7c5270b168832014-09-20View Spectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS, GC-MS Spectrumsplash10-00ko-9700000000-1a891469df1de787159bSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-0006-1900000000-7dc1a5344d13e4dc19acSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-bbbc84c54d03c4a14e51Spectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-00b547b0371603520b61Spectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS; 1 MEOX, GC-MS Spectrumsplash10-00di-9100000000-fdd48b632e63c8478078Spectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000f-9300000000-8cd32f87e04ae0b6d6fbSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-014u-9720000000-7a0b66e6c18ff42ac05eSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 2 TMS, GC-MS Spectrumsplash10-0006-9760000000-d94111a7b9babceb265bSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-00ko-9700000000-1a891469df1de787159bSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-00di-9100000000-fdd48b632e63c8478078Spectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-000f-9300000000-8cd32f87e04ae0b6d6fbSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-014u-9720000000-7a0b66e6c18ff42ac05eSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-0006-9760000000-d94111a7b9babceb265bSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-000f-9300000000-8cd32f87e04ae0b6d6fbSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-014u-9720000000-7a0b66e6c18ff42ac05eSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-0006-9760000000-d94111a7b9babceb265bSpectrum
GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrumsplash10-00ko-9700000000-cec4a53271b8d66c2abcSpectrum
Predicted GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9300000000-9a8a36c751256480752eSpectrum
Predicted GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r6-9500000000-3e83cb905f1fd4362497Spectrum
Predicted GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-066r-0900000000-ceb2ce23352e0f45ee332012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9200000000-ed4a6740d574858da9822012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-c239a9a599daa607e47f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-36e00f6baa5d907e851b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-014i-0900000000-843a66173124c8fdf1842020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0900000000-272f6079d347e1b34e862021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-1900000000-5d025096b1bb0e80dc1c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3900000000-9d0be907ecb6cc5efe8c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-a4fc563b3536eafc044d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-0f660ae6dc074d9394042016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1900000000-d229883bf098b04e0fcb2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5900000000-a107b725b71a6441a80c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-1900000000-8ba05dd4c5612aae9f502021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-946fa61c2a2596d7592d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-fa13a9bfbb6c03b2e12d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-4900000000-2d56731d3ebcebf8079a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-9b3ae8fbf3992b1b2f282021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-089373761153dce3ca742021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID972
ChEMBL IDCHEMBL1162488
KEGG Compound IDC00166
Pubchem Compound ID997
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB03884
HMDB IDHMDB00205
CRC / DFC (Dictionary of Food Compounds) IDDFK71-H:DFK71-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34111
KNApSAcK IDC00000751
HET IDPPY
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Tyrosine aminotransferaseTATP17735
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Macrophage migration inhibitory factorMIFP14174
Pathways
NameSMPDB LinkKEGG Link
Phenylalanine and Tyrosine MetabolismSMP00008 map00360
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference