Showing metabocard for Phenylpyruvic acid (MMDBc0029479)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:23:57 UTC
Update Date2024-09-29 09:57:39 UTC
Metabolite IDMMDBc0029479
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. 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f92509b83b0>


  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 #<Metabolite:0x00007f92509b83b0>

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 #<Metabolite:0x00007f92509b83b0>


  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>
MMDBc0029479

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f92509b83b0>

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 #<Metabolite:0x00007f92509b83b0>

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 #<Metabolite:0x00007f92509b83b0>

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 #<Metabolite:0x00007f92509b83b0>

OC(=O)C(=O)CC1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f92509b83b0>

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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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
Molecular FormulaC9H8O3
Average Mass164.158
Monoisotopic Mass164.047344122
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