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Showing metabocard for Phenylglyoxylic acid (HMDB0001587)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-12-21 14:22:10 UTC
Update Date2023-02-21 17:15:48 UTC
HMDB IDHMDB0001587
Secondary Accession Numbers
  • HMDB01587
Metabolite Identification
Common NamePhenylglyoxylic acid
DescriptionPhenylglyoxylic acid, also known as benzoylformate or 2-oxo-2-phenylacetate, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Phenylglyoxylic acid exists in all living organisms, ranging from bacteria to humans. Phenylglyoxylic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make phenylglyoxylic acid a potential biomarker for the consumption of these foods. Phenylglyoxylic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Phenylglyoxylic acid.
Structure
Data?1676999748
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001587 (Phenylglyoxylic acid)

  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 HMDB0001587 (Phenylglyoxylic acid)

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 HMDB0001587 (Phenylglyoxylic acid)

  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>
HMDB0001587

> <DATABASE_NAME>
hmdb

> <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 HMDB0001587 (Phenylglyoxylic acid)

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 HMDB0001587 (Phenylglyoxylic acid)

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 HMDB0001587 (Phenylglyoxylic acid)

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 HMDB0001587 (Phenylglyoxylic acid)

OC(=O)C(=O)C1=CC=CC=C1
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INCHI for HMDB0001587 (Phenylglyoxylic acid)

InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H6O3
Average Molecular Weight150.1314
Monoisotopic Molecular Weight150.031694058
IUPAC Name2-oxo-2-phenylacetic acid
Traditional Namebenzoylformic acid
CAS Registry Number611-73-4
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct ParentBenzoyl derivatives
Alternative Parents
Substituents
  • Aryl ketone
  • Benzoyl
  • 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point66 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility920 mg/mL at 0 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified36.6 +/- 0.48 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.019 (0.015-0.024) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified7.34 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified62.9 +/- 1.18 umol/mmol creatinineAdult (>18 years old)BothOccupational exposure to styrene details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02279
Phenol Explorer Compound IDNot Available
FooDB IDFDB022696
KNApSAcK IDC00052384
Chemspider ID11421
KEGG Compound IDC02137
BioCyc IDPHENYLGLYOXYLATE
BiGG IDNot Available
Wikipedia LinkPhenylglyoxylic_acid
METLIN IDNot Available
PubChem Compound11915
PDB IDNot Available
ChEBI ID18280
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHurd, Charles D.; McNamee, R. W.; Green, Frank O. Benzoylformic acid from styrene. Journal of the American Chemical Society (1939), 61 2979-80.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lacroix C, Inger F, Menager S, Lafont O: [Simultaneous determination of urinary hippuric acid and o-, m-, p-methylhippuric acids with liquid chromatography]. J Chromatogr. 1986 Oct 31;382:275-9. [PubMed:3782394 ]
  2. Sakai T, Takeuchi Y, Ikeya Y, Araki T, Ushio K: [Method for simultaneous determination of six metabolites of toluene, xylene and ethylbenzene, and its application to exposure monitoring of workers in a printing factory with gravure machines]. Sangyo Igaku. 1989 Jan;31(1):9-16. [PubMed:2739101 ]