Showing metabocard for 3-phenylpyruvic acid (MMDBc0054239)

Microbial
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:01:03 UTC
Update Date2025-10-07 16:08:26 UTC
Metabolite IDMMDBc0054239
Metabolite Identification
Common Name3-phenylpyruvic acid
Description3-phenylpyruvic acid is a member of the class of organic compounds known as α-keto acids. Its chemical structure features a phenyl group attached to a pyruvic acid backbone, characterized by a keto functional group at the second carbon position. This compound is involved in several metabolic pathways, notably the shikimic acid pathway, which is crucial for the biosynthesis of aromatic amino acids. Evidence suggests that boron deficiency can enhance the synthesis of 3-phenylpyruvic acid alongside other metabolites like l-phenylalanine and salicylic acid, indicating its role in plant metabolism (PMID:36611002 ). Additionally, 3-phenylpyruvic acid has been shown to enhance insulin release and glucose uptake in muscle cells, highlighting its potential significance in glucose metabolism and energy regulation (PMID:23943314 ). Furthermore, its insulin-releasing effects have been examined in clonal beta cells, suggesting a role in pancreatic function and glucose homeostasis (PMID:10630382 ). Overall, 3-phenylpyruvic acid serves as an important metabolite with implications in both plant and animal biochemical pathways.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f2e50f3d0d8>


  Mrv0541 02241222532D          

 12 12  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
M  CHG  1   1  -1
M  END
Download

3D MOL for #<Metabolite:0x00007f2e50f3d0d8>

HMDB0304081
     RDKit          3D
2-oxo-3-phenylpropanoate
 19 19  0  0  0  0  0  0  0  0999 V2000
    4.1269   -0.4800   -0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    0.2263    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627    0.9474    1.4513 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0943    0.2684    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    0.9927    1.5978 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -0.4948   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330   -0.2694    0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884    0.7572   -0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    1.0386   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022    0.2403    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2565   -0.7987    1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290   -1.0512    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4450   -0.1796   -1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -1.5932   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930    1.4024   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    1.8538   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9545    0.4379    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168   -1.4166    1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4181   -1.8814    1.5321 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
  6 13  1  0
  6 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
 12 19  1  0
M  CHG  1   3  -1
M  END
Download

3D SDF for #<Metabolite:0x00007f2e50f3d0d8>


  Mrv0541 02241222532D          

 12 12  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
M  CHG  1   1  -1
M  END
> <DATABASE_ID>
MMDBc0054239

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=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)/p-1

> <INCHI_KEY>
BTNMPGBKDVTSJY-UHFFFAOYSA-M

> <FORMULA>
C9H7O3

> <MOLECULAR_WEIGHT>
163.1501

> <EXACT_MASS>
163.03951909

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
15.336641886787511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-3-phenylpropanoate

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
1.9002137729999997

> <ALOGPS_LOGS>
-2.16

> <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>
57.199999999999996

> <JCHEM_REFRACTIVITY>
53.54870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-phenylpyruvate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f2e50f3d0d8>

HMDB0304081
     RDKit          3D
2-oxo-3-phenylpropanoate
 19 19  0  0  0  0  0  0  0  0999 V2000
    4.1269   -0.4800   -0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    0.2263    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627    0.9474    1.4513 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0943    0.2684    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    0.9927    1.5978 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -0.4948   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2330   -0.2694    0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884    0.7572   -0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    1.0386   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022    0.2403    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2565   -0.7987    1.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9290   -1.0512    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4450   -0.1796   -1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -1.5932   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930    1.4024   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    1.8538   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9545    0.4379    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168   -1.4166    1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4181   -1.8814    1.5321 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
  6 13  1  0
  6 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
 11 18  1  0
 12 19  1  0
M  CHG  1   3  -1
M  END
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PDB for #<Metabolite:0x00007f2e50f3d0d8>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x00007f2e50f3d0d8>

COMPND    HMDB0304081
HETATM    1  O1  UNL     1       4.127  -0.480  -0.275  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.542   0.226   0.602  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.363   0.947   1.451  1.00  0.00           O1-
HETATM    4  C2  UNL     1       2.094   0.268   0.701  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.595   0.993   1.598  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.199  -0.495  -0.196  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.233  -0.269   0.125  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.888   0.757  -0.497  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.238   1.039  -0.251  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.902   0.240   0.649  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.257  -0.799   1.284  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.929  -1.051   1.023  1.00  0.00           C  
HETATM   13  H1  UNL     1       1.445  -0.180  -1.238  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.412  -1.593  -0.133  1.00  0.00           H  
HETATM   15  H3  UNL     1      -0.393   1.402  -1.210  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.748   1.854  -0.748  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.955   0.438   0.859  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.817  -1.417   1.998  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.418  -1.881   1.532  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5    6
CONECT    6    7   13   14
CONECT    7    8    8   12
CONECT    8    9   15
CONECT    9   10   10   16
CONECT   10   11   17
CONECT   11   12   12   18
CONECT   12   19
END
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SMILES for #<Metabolite:0x00007f2e50f3d0d8>

[O-]C(=O)C(=O)CC1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f2e50f3d0d8>

InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)/p-1
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Synonyms
ValueSource
3-(4-Hydroxyphenyl)pyruvateChEBI
3-Phenyl-2-oxopropanoateChEBI
3-PhenylpyruvateChEBI
3-(4-Hydroxyphenyl)pyruvic acidGenerator
3-Phenyl-2-oxopropanoic acidGenerator
3-Phenylpyruvic acidGenerator
Keto-phenylpyruvic acidGenerator
β-phenylpyruvic acidGenerator
2-oxo-3-Phenylpropanoic acidGenerator
beta-Phenylpyruvic acidMeSH
PhenylpyruvateMeSH
Phenylpyruvic acid, calcium saltMeSH
Phenylpyruvic acid, sodium saltMeSH
Phenylpyruvic acidMeSH
Molecular FormulaC9H7O3
Average Mass163.1501
Monoisotopic Mass163.03951909
IUPAC Name2-oxo-3-phenylpropanoate
Traditional Nameβ-phenylpyruvate
CAS Registry NumberNot Available
SMILES
[O-]C(=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)/p-1
InChI KeyBTNMPGBKDVTSJY-UHFFFAOYSA-M