Showing metabocard for phenylglyoxylate (MMDBc0054632)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:21:49 UTC
Update Date2024-04-30 20:54:56 UTC
Metabolite IDMMDBc0054632
Metabolite Identification
Common Namephenylglyoxylate
DescriptionPhenylglyoxylic acid is one of the major urinary metabolites of toluene, o-, m- and p-xylenes, styrene and ethylbenzene. (PMID 3782394 ). For the biological monitoring of workers exposure to solvent used in industry, its concentration is measured in human urine samples. (PMID 2739101 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa50bb64650>


  Mrv1652305271900262D          

 11 11  0  0  0  0            999 V2000
    0.0000    3.3000    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
    1.4289    2.4750    0.0000 O   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fa50bb64650>

HMDB0001587
     RDKit          3D
Phenylglyoxylic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.4289    1.4153   -0.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856    0.4219    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8755    0.1256    0.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -0.3770    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -1.3791    1.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.2005    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4166    0.8054   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    0.9486   -0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6523    0.0275   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.9917    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8657   -1.1040    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    0.5437    0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455    1.5301   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324    1.7610   -1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055    0.1164   -0.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8805   -1.7268    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368   -1.9163    1.3048 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007fa50bb64650>


  Mrv1652305271900262D          

 11 11  0  0  0  0            999 V2000
    0.0000    3.3000    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
    1.4289    2.4750    0.0000 O   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054632

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)

> <INCHI_KEY>
FAQJJMHZNSSFSM-UHFFFAOYSA-N

> <FORMULA>
C8H6O3

> <MOLECULAR_WEIGHT>
150.1314

> <EXACT_MASS>
150.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.074629888520002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-2-phenylacetic acid

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
1.4904874796666667

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6860857287720954

> <JCHEM_PKA_STRONGEST_BASIC>
-9.541268827596856

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
38.255700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzoylformic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fa50bb64650>

HMDB0001587
     RDKit          3D
Phenylglyoxylic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.4289    1.4153   -0.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856    0.4219    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8755    0.1256    0.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -0.3770    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -1.3791    1.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.2005    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4166    0.8054   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7560    0.9486   -0.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6523    0.0275   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.9917    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8657   -1.1040    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    0.5437    0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455    1.5301   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324    1.7610   -1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055    0.1164   -0.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8805   -1.7268    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368   -1.9163    1.3048 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
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PDB for #<Metabolite:0x00007fa50bb64650>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  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   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007fa50bb64650>

COMPND    HMDB0001587
HETATM    1  O1  UNL     1       2.429   1.415  -0.606  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.586   0.422   0.120  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.875   0.126   0.524  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.472  -0.377   0.518  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.756  -1.379   1.270  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.082  -0.201   0.184  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.417   0.805  -0.603  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.756   0.949  -0.906  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.652   0.027  -0.389  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.199  -0.992   0.400  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.866  -1.104   0.681  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.699   0.544   0.103  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.246   1.530  -1.016  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.132   1.761  -1.537  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.705   0.116  -0.610  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.881  -1.727   0.818  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.537  -1.916   1.305  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5    6
CONECT    6    7    7   11
CONECT    7    8   13
CONECT    8    9    9   14
CONECT    9   10   15
CONECT   10   11   11   16
CONECT   11   17
END
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SMILES for #<Metabolite:0x00007fa50bb64650>

OC(=O)C(=O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x00007fa50bb64650>

InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
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Synonyms
ValueSource
2-oxo-2-PhenylacetateChEBI
2-oxo-2-Phenylacetic acidChEBI
2-Phenylethanoic acidChEBI
alpha-Ketophenylacetic acidChEBI
alpha-oxo-Benzeneacetic acidChEBI
Benzeneglyoxylic acidChEBI
BENZOYL-formIC ACIDChEBI
BenzoylformateChEBI
Benzoylformic acidChEBI
PhenylglyoxylateChEBI
2-PhenylethanoateGenerator
a-KetophenylacetateGenerator
a-Ketophenylacetic acidGenerator
alpha-KetophenylacetateGenerator
Α-ketophenylacetateGenerator
Α-ketophenylacetic acidGenerator
a-oxo-BenzeneacetateGenerator
a-oxo-Benzeneacetic acidGenerator
alpha-oxo-BenzeneacetateGenerator
Α-oxo-benzeneacetateGenerator
Α-oxo-benzeneacetic acidGenerator
BenzeneglyoxylateGenerator
BENZOYL-formateGenerator
a-Oxobenzeneacetic acidHMDB
alpha-Oxobenzeneacetic acidHMDB
Oxophenylacetic acidHMDB
Phenylgloxylic acidHMDB
Phenyloxoacetic acidHMDB
Phenylglyoxilic acidMeSH, HMDB
Phenylglyoxylic acid, calcium saltMeSH, HMDB
Phenylglyoxylic acid, potassium saltMeSH, HMDB
Phenylglyoxylic acid, sodium saltMeSH, HMDB
Phenylglyoxylic hydrochlorideMeSH, HMDB
Phenylglyoxylic acidKEGG
Molecular FormulaC8H6O3
Average Mass150.1314
Monoisotopic Mass150.031694058
IUPAC Name2-oxo-2-phenylacetic acid
Traditional Namebenzoylformic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
InChI KeyFAQJJMHZNSSFSM-UHFFFAOYSA-N