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Showing NP-Card for Phenylglyoxylic acid (NP0000984)

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Record Information
Version2.0
Created at2005-12-21 14:22:10 UTC
Updated at2024-09-03 04:22:33 UTC
NP-MRD IDNP0000984
Natural Product DOIhttps://doi.org/10.57994/2901
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenylglyoxylic acid
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
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MOLSDFPDBSMILESInChI

MOL for NP0000984 (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 NP0000984 (Phenylglyoxylic acid)

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3D SDF for NP0000984 (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>
NP0000984

> <DATABASE_NAME>
NP-MRD

> <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 NP0000984 (Phenylglyoxylic acid)
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PDB for NP0000984 (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 NP0000984 (Phenylglyoxylic acid)
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SMILES for NP0000984 (Phenylglyoxylic acid)
OC(=O)C(=O)C1=CC=CC=C1
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INCHI for NP0000984 (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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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 acidHMDB
Phenylglyoxylic acid, calcium saltHMDB
Phenylglyoxylic acid, potassium saltHMDB
Phenylglyoxylic acid, sodium saltHMDB
Phenylglyoxylic hydrochlorideHMDB
Phenylglyoxylic acidKEGG
Chemical FormulaC8H6O3
Average Mass150.1314 Da
Monoisotopic Mass150.03169 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-21View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-21View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-21View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-21View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Homo sapiens (Urine)Animalia
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
Vitis vinifera
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point66 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility920 mg/mL at 0 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP1.16ALOGPS
logP1.49ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.69ChemAxon
pKa (Strongest Basic)-9.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.26 m³·mol⁻¹ChemAxon
Polarizability14.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001587  
DrugBank IDDB02279  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022696  
KNApSAcK IDNot Available
Chemspider ID11421  
KEGG Compound IDC02137  
BioCyc IDPHENYLGLYOXYLATE  
BiGG IDNot Available
Wikipedia LinkPhenylglyoxylic_acid  
METLIN IDNot Available
PubChem Compound11915  
PDB IDNot Available
ChEBI ID18280  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. Sperlingova I, Dabrowska L, Stransky V, Tichy M: A rapid HPLC method for the determination of carboxylic acids in human urine using a monolithic column. Anal Bioanal Chem. 2004 Jan;378(2):536-43. doi: 10.1007/s00216-003-2289-z. Epub  2003 Nov 4. [PubMed:14598013  ] 
  3. Terre'Blanche G, Heyer N, Bergh JJ, Mienie LJ, van der Schyf CJ, Harvey BH: The styrene metabolite, phenylglyoxylic acid, induces striatal-motor toxicity in the rat: influence of dose escalation/reduction over time. Neurotox Res. 2011 Jul;20(1):97-101. doi: 10.1007/s12640-010-9222-y. Epub 2010  Oct 8. [PubMed:20931367  ] 
  4. Linhart I, Mraz J, Dabrowska L, Malis M, Krouzelka J, Korinek M: Vinylphenylmercapturic acids in human urine as biomarkers of styrene ring oxidation. Toxicol Lett. 2012 Sep 3;213(2):260-5. doi: 10.1016/j.toxlet.2012.06.012. Epub  2012 Jun 28. [PubMed:22750350  ] 
  5. bieniek G, Palys E, Wilczok T: TLC separation of hippuric, mandelic, and phenylglyoxylic acids from urine after mixed exposure to toluene and styrene. Br J Ind Med. 1982 May;39(2):187-90. doi: 10.1136/oem.39.2.187. [PubMed:7066236  ]