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Showing NP-Card for Phenylpyruvic acid (NP0001083)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:45 UTC
NP-MRD IDNP0001083
Secondary Accession NumbersNone
Natural Product 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.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001083 (Phenylpyruvic acid)


  Mrv1652309032023562D          

 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 NP0001083 (Phenylpyruvic acid)

HMDB0000205
     RDKit          3D
Phenylpyruvic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.7055    0.6146   -0.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2873   -0.1343    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2209   -0.8193    0.9541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8654   -0.2629    0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960   -1.0014    1.3262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153    0.4963   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    0.2517   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.7689   -0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -1.0423   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174   -0.2315    0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545    0.8032    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380    1.0361    0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8502   -0.2536    1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    1.5768   -0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497    0.1254   -1.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257   -1.3958   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -1.8418   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.4007    0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    1.4023    1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171    1.8461    1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  6 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0001083 (Phenylpyruvic acid)


  Mrv1652309032023562D          

 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>
NP0001083

> <DATABASE_NAME>
NP-MRD

> <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

> <JCHEM_LOGP>
1.9002137729999997

> <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

> <JCHEM_TRADITIONAL_IUPAC>
phenylpyruvic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001083 (Phenylpyruvic acid)

HMDB0000205
     RDKit          3D
Phenylpyruvic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.7055    0.6146   -0.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2873   -0.1343    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2209   -0.8193    0.9541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8654   -0.2629    0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3960   -1.0014    1.3262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153    0.4963   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4899    0.2517   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.7689   -0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -1.0423   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174   -0.2315    0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545    0.8032    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1380    1.0361    0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8502   -0.2536    1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    1.5768   -0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497    0.1254   -1.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257   -1.3958   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -1.8418   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1421   -0.4007    0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    1.4023    1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171    1.8461    1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3 13  1  0
  6 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

PDB for NP0001083 (Phenylpyruvic acid)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-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
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3D PDB for NP0001083 (Phenylpyruvic acid)

COMPND    HMDB0000205
HETATM    1  O1  UNL     1      -3.705   0.615  -0.710  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.287  -0.134   0.197  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.221  -0.819   0.954  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.865  -0.263   0.428  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.396  -1.001   1.326  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.915   0.496  -0.415  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.490   0.252  -0.048  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.205  -0.769  -0.638  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.515  -1.042  -0.334  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.117  -0.231   0.616  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.455   0.803   1.240  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.138   1.036   0.899  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.850  -0.254   1.515  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.182   1.577  -0.429  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.050   0.125  -1.457  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.726  -1.396  -1.378  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.089  -1.842  -0.791  1.00  0.00           H  
HETATM   18  H6  UNL     1       4.142  -0.401   0.892  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.978   1.402   1.975  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.617   1.846   1.386  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5    6
CONECT    6    7   14   15
CONECT    7    8    8   12
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   11   18
CONECT   11   12   12   19
CONECT   12   20
END
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SMILES for NP0001083 (Phenylpyruvic acid)

OC(=O)C(=O)CC1=CC=CC=C1
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INCHI for NP0001083 (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 JSmol
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
2-oxo-3-PhenylpropanoateKegg
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-Phenylpropanoic acidGenerator
a-Hydroxycinnamic acidHMDB
FEMA 3892HMDB
2-oxo-3-Phenylpropionic acidHMDB
3-Phenyl-2-oxopropionic acidHMDB
alpha-Oxobenzenepropanoic acidHMDB
alpha-Oxobenzenepropionic acidHMDB
Α-oxobenzenepropanoic acidHMDB
Α-oxobenzenepropionic acidHMDB
Phenylpyruvic acidChEBI
Chemical FormulaC9H8O3
Average Mass164.1580 Da
Monoisotopic Mass164.04734 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Varshavi.d262021-08-22View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-17View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloe africanaLOTUS Database
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
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Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Pseudomonas sp.KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point154 °CNot Available
Boiling Point299.00 to 300.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility112 mg/mLNot Available
LogP0.142 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.93 g/LALOGPS
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
HMDB IDHMDB0000205
DrugBank IDDB03884
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020197
KNApSAcK IDC00000751
Chemspider ID972
KEGG Compound IDC00166
BioCyc IDPHENYL-PYRUVATE
BiGG ID34111
Wikipedia LinkPhenylpyruvic_acid
METLIN ID328
PubChem Compound997
PDB IDNot Available
ChEBI ID30851
Good Scents IDrw1274191
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. Lasala JM, Coscia CJ: Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science. 1979 Jan 19;203(4377):283-4. [PubMed:153583 ]
  5. 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 ]
  6. Michals K, Matalon R: Phenylalanine metabolites, attention span and hyperactivity. Am J Clin Nutr. 1985 Aug;42(2):361-5. [PubMed:4025205 ]
  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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .