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Showing metabocard for Phenylpyruvic acid (HMDB0000205)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (8) Show 8 proteinsXML
enzymes (8) Show 8 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:12:43 UTC
HMDB IDHMDB0000205
Secondary Accession Numbers
  • HMDB0001237
  • HMDB00205
  • HMDB0031629
  • HMDB01237
  • HMDB31629
Metabolite Identification
Common NamePhenylpyruvic acid
DescriptionPhenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Levels of phenylpyruvate are normally very low in blood or urine. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but 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. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. 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. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. Phenylpyruvic acid is also a microbial metabolite, it can be produced by Lactobacillus plantarum (PMID: 9687465 ).
Structure
Data?1587397693
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000205 (Phenylpyruvic acid)


  Mrv1652304202017462D          

 12 12  0  0  0  0            999 V2000
   -0.7698    0.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843    0.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988    0.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -1.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    0.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735    0.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3734    1.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879    0.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000205 (Phenylpyruvic acid)

Download
3D SDF for HMDB0000205 (Phenylpyruvic acid)

  Mrv1652304202017462D          

 12 12  0  0  0  0            999 V2000
   -0.7698    0.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843    0.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988    0.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -1.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    0.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735    0.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3734    1.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879    0.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000205

> <DATABASE_NAME>
hmdb

> <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_KEY>
BTNMPGBKDVTSJY-UHFFFAOYSA-N

> <FORMULA>
C9H8O3

> <MOLECULAR_WEIGHT>
164.158

> <EXACT_MASS>
164.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.750874725076514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-oxo-3-phenylpropanoic acid

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
1.9002137729999997

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.097510920786018

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.332859227478436

> <JCHEM_PKA_STRONGEST_BASIC>
-9.757724229361303

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
42.711600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylpyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0000205 (Phenylpyruvic acid)
https://cactus.nci.nih.gov/chemical/structure/OC(=O)C(=O)CC1=CC=CC=C1/file?fo...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:19})
 20 20  0  0  0  0  0  0  0  0999 V2000
    3.6303    1.0033    0.0305 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7932   -0.0501   -0.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385   -1.1776   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188    0.1691    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.2920    0.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815   -1.0105   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -0.5204   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970   -0.2593   -1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    0.1903   -1.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6580    0.3784    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047    0.1165    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -0.3372    1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5780    0.8113    0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579   -1.5873   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5578   -1.6412    0.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863   -0.4064   -2.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5145    0.3949   -2.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6789    0.7305    0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153    0.2638    2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886   -0.5419    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 11 12  2  0  0  0  0
 11 19  1  0  0  0  0
 12 20  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0000205 (Phenylpyruvic acid)
HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      -1.437   0.166   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.771   0.936   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.104   0.166   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.105  -1.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.771  -2.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.437  -1.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.103   0.936   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.230   0.166   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.230  -1.374   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.564   0.936   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.564   2.476   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.897   0.166   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for HMDB0000205 (Phenylpyruvic acid)
COMPND    https://cactus.nci.nih.gov/chemical/structure/OC(=O)C(=O)CC1=CC=CC=C1/file?fo... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1       3.630   1.003   0.030  1.00  0.00           O  
HETATM    2  C   UNL     1       2.793  -0.050  -0.001  1.00  0.00           C  
HETATM    3  O   UNL     1       3.239  -1.178  -0.035  1.00  0.00           O  
HETATM    4  C   UNL     1       1.319   0.169   0.005  1.00  0.00           C  
HETATM    5  O   UNL     1       0.875   1.292   0.039  1.00  0.00           O  
HETATM    6  C   UNL     1       0.382  -1.010  -0.031  1.00  0.00           C  
HETATM    7  C   UNL     1      -1.044  -0.520  -0.016  1.00  0.00           C  
HETATM    8  C   UNL     1      -1.697  -0.259  -1.206  1.00  0.00           C  
HETATM    9  C   UNL     1      -3.004   0.190  -1.192  1.00  0.00           C  
HETATM   10  C   UNL     1      -3.658   0.378   0.011  1.00  0.00           C  
HETATM   11  C   UNL     1      -3.005   0.117   1.201  1.00  0.00           C  
HETATM   12  C   UNL     1      -1.699  -0.337   1.187  1.00  0.00           C  
HETATM   13  H   UNL     1       4.578   0.811   0.025  1.00  0.00           H  
HETATM   14  H   UNL     1       0.558  -1.587  -0.939  1.00  0.00           H  
HETATM   15  H   UNL     1       0.558  -1.641   0.841  1.00  0.00           H  
HETATM   16  H   UNL     1      -1.186  -0.406  -2.146  1.00  0.00           H  
HETATM   17  H   UNL     1      -3.514   0.395  -2.122  1.00  0.00           H  
HETATM   18  H   UNL     1      -4.679   0.731   0.022  1.00  0.00           H  
HETATM   19  H   UNL     1      -3.515   0.264   2.141  1.00  0.00           H  
HETATM   20  H   UNL     1      -1.189  -0.542   2.117  1.00  0.00           H  
CONECT    1    2   13                                                 
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5    5    6                                       
CONECT    5    4    4                                                 
CONECT    6    4    7   14   15                                       
CONECT    7    6    8    8   12                                       
CONECT    8    7    7    9   16                                       
CONECT    9    8   10   10   17                                       
CONECT   10    9    9   11   18                                       
CONECT   11   10   12   12   19                                       
CONECT   12   11   11    7   20                                       
CONECT   13    1                                                      
CONECT   14    6                                                      
CONECT   15    6                                                      
CONECT   16    8                                                      
CONECT   17    9                                                      
CONECT   18   10                                                      
CONECT   19   11                                                      
CONECT   20   12                                                      
MASTER        0    0    0    0    0    0    0    0   20    0   20    0
END

Download
SMILES for HMDB0000205 (Phenylpyruvic acid)
OC(=O)C(=O)CC1=CC=CC=C1
Download
INCHI for HMDB0000205 (Phenylpyruvic acid)
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
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View in JSmolView Stereo Labels
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
Physiological effect
Health effect:
Disposition
Source:
Biological location:
Process
Naturally occurring process:
Role
Industrial application:
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
Water Solubility0.93 g/LALOGPS
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 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
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00ko-9700000000-1a891469df1de787159b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-1900000000-7dc1a5344d13e4dc19ac2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0900000000-bbbc84c54d03c4a14e512014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0900000000-00b547b0371603520b612014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX)splash10-00di-9100000000-fdd48b632e63c84780782014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000f-9300000000-8cd32f87e04ae0b6d6fb2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-014u-9720000000-7a0b66e6c18ff42ac05e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0006-9760000000-d94111a7b9babceb265b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ko-9700000000-1a891469df1de787159b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9100000000-fdd48b632e63c84780782017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000f-9300000000-8cd32f87e04ae0b6d6fb2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014u-9720000000-7a0b66e6c18ff42ac05e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9760000000-d94111a7b9babceb265b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000f-9300000000-8cd32f87e04ae0b6d6fb2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014u-9720000000-7a0b66e6c18ff42ac05e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9760000000-d94111a7b9babceb265b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ko-9700000000-cec4a53271b8d66c2abc2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-9a8a36c751256480752e2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-9500000000-3e83cb905f1fd43624972017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-9300000000-d1a7d23e7c5270b168832014-09-20View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-066r-0900000000-ceb2ce23352e0f45ee332012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9200000000-ed4a6740d574858da9822012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-c239a9a599daa607e47f2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-36e00f6baa5d907e851b2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-014i-0900000000-843a66173124c8fdf1842020-07-21View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-014j-1900000000-5d025096b1bb0e80dc1c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-014m-3900000000-9d0be907ecb6cc5efe8c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0006-9200000000-a4fc563b3536eafc044d2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-03di-1900000000-0f660ae6dc074d9394042016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-014j-1900000000-d229883bf098b04e0fcb2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-014i-5900000000-a107b725b71a6441a80c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-03xr-1900000000-8ba05dd4c5612aae9f502021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0006-9300000000-946fa61c2a2596d7592d2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0006-9200000000-fa13a9bfbb6c03b2e12d2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-014l-4900000000-2d56731d3ebcebf8079a2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0006-9200000000-9b3ae8fbf3992b1b2f282021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0006-9000000000-089373761153dce3ca742021-09-07View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
    • 

  • Mitochondria
Biospecimen Locations
  • Blood
    • 

  • Feces
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
BloodDetected and Quantified0.5 +/- 0.1 uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified5 uMChildren (1 - 13 years old)BothNormal  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
UrineDetected and Quantified0.17 (0.05-0.67) umol/mmol creatinineAdult (>18 years old)MaleNormal  details
UrineDetected and Quantified0.24 (0.10-0.76) umol/mmol creatinineAdult (>18 years old)FemaleNormal  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
UrineDetected and Quantified0.00064 +/- 0.000544 umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal  details
UrineDetected and Quantified<2 umol/mmol creatinineChildren (1 - 18 years old)Both
 
Normal
    • BC Children's Hos...
  details
UrineDetected and Quantified0.138 +/- 0.207 umol/mmol creatinineInfant (0-1 year old)Both
 
Normal		  details
UrineDetected and Quantified0.207 +/- 0.275 umol/mmol creatinineInfant (0-1 year old)BothNormal  details
UrineDetected and Quantified0.207 +/- 0.344 umol/mmol creatinineInfant (0-1 year old)Both
 
Normal		  details
UrineDetected and Quantified0.25 +/- 0.43 umol/mmol creatinineInfant (0-1 year old)BothNormal  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified50.0 (40.0-60.0) uMNewborn (0-30 days old)BothPhenylketonuria  details
BloodDetected and Quantified1.4 +/- 0.2 uMAdult (>18 years old)BothPrimary biliary cirrhosis  details
UrineDetected and Quantified7796.386 umol/mmol creatinineInfant (0-1 year old)MalePhenylketonuria  details
UrineDetected and Quantified31047.8 umol/mmol creatinineChildren (1 - 13 years old)MalePhenylketonuria  details
UrineDetected and Quantified255.518 +/- 250.00780 umol/mmol creatinineChildren (1-13 years old)BothPhenylketonuria  details
UrineDetected and Quantified735.560 +/- 528.253 umol/mmol creatinineChildren (1-13 years old)Both
 
Phenylketonuria		  details
UrineDetected and Quantified882.948 +/- 741.0699 umol/mmol creatinineChildren (1-13 years old)Both
 
Phenylketonuria		  details
UrineDetected and Quantified146.6 +/- 244.6 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria  details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. Langenbeck U, Behbehani A, Luthe H: Renal transport of aromatic acids in patients with phenylketonuria. J Inherit Metab Dis. 1981;4(2):69-70. [PubMed:6790852  ] 
  2. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926  ] 
  3. Swarna M, Jyothy A, Usha Rani P, Reddy PP: Amino acid disorders in mental retardation: a two-decade study from Andhra Pradesh. Biochem Genet. 2004 Apr;42(3-4):85-98. [PubMed:15168722  ] 
  4. Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567  ] 
  5. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium. 
Primary biliary cirrhosis
  1. Turchany JM, Leung PS, Iwayama T, Jefferson DM, Ishida J, Yamaguchi M, Munoz S, Danner DJ, Dickson ER, Gershwin ME: Comparative metabolism and structure of BCKD-E2 in primary biliary cirrhosis. J Autoimmun. 1993 Aug;6(4):459-66. [PubMed:8216688  ] 
Associated OMIM IDs
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  
Food Biomarker OntologyNot Available
VMH IDPHPYR  
MarkerDB IDMDB00000098  
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)Download (PDF)
General References
  1. Lasala JM, Coscia CJ: Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science. 1979 Jan 19;203(4377):283-4. [PubMed:153583  ] 
  2. 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  ] 
  3. 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  ] 
  4. Michals K, Matalon R: Phenylalanine metabolites, attention span and hyperactivity. Am J Clin Nutr. 1985 Aug;42(2):361-5. [PubMed:4025205  ] 
  5. 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  ] 
  6. 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  ] 
  7. 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  ] 
  8. Nierop Groot MN, de Bont JAM: Conversion of phenylalanine to benzaldehyde initiated by an aminotransferase in lactobacillus plantarum Appl Environ Microbiol. 1998 Aug;64(8):3009-13. [PubMed:9687465  ] 
  9.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. . 
Enzymes
  Enzyme Details
1. Macrophage migration inhibitory factor
General function:
Involved in cell surface binding
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.

Gene Name:
MIF
Uniprot ID:
P14174  
Molecular weight:
12476.19
Reactions
Phenylpyruvic acid → Enol-phenylpyruvatedetails
Phenylpyruvic acid → Enol-phenylpyruvatedetails
  Enzyme Details
2. Tyrosine aminotransferase
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
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 towards phenylalanine.

Gene Name:
TAT
Uniprot ID:
P17735  
Molecular weight:
50398.895
Reactions
L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic aciddetails
  Enzyme Details
3. Aspartate aminotransferase, cytoplasmic
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).

Gene Name:
GOT1
Uniprot ID:
P17174  
Molecular weight:
46247.14
Reactions
L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic aciddetails
  Enzyme Details
4. Aspartate aminotransferase, mitochondrial
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.

Gene Name:
GOT2
Uniprot ID:
P00505  
Molecular weight:
47517.285
Reactions
L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic aciddetails
  Enzyme Details
5. Kynurenine--oxoglutarate transaminase 1
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.

Gene Name:
CCBL1
Uniprot ID:
Q16773  
Molecular weight:
47874.765
Reactions
L-Glutamine + Phenylpyruvic acid → 2-Keto-glutaramic acid + L-Phenylalaninedetails
  Enzyme Details
6. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.

Gene Name:
UGT1A1
Uniprot ID:
P22309  
Molecular weight:
59590.91
Reactions
Phenylpyruvic acid → 3,4,5-trihydroxy-6-[(2-oxo-3-phenylpropanoyl)oxy]oxane-2-carboxylic aciddetails
  Enzyme Details
7. 4-hydroxyphenylpyruvate dioxygenase
General function:
Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:
Key enzyme in the degradation of tyrosine.

Gene Name:
HPD
Uniprot ID:
P32754  
Molecular weight:
40497.105
Reactions
Phenylpyruvic acid + Oxygen → ortho-Hydroxyphenylacetic acid + Carbon dioxidedetails
  Enzyme Details
8. L-amino-acid oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).

Gene Name:
IL4I1
Uniprot ID:
Q96RQ9  
Molecular weight:
65327.26
Reactions
L-Phenylalanine + Water + Oxygen → Phenylpyruvic acid + Ammonia + Hydrogen peroxidedetails