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Showing metabocard for Phenylglyoxal (HMDB0061916)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:57:16 UTC
Update Date2023-02-21 17:30:34 UTC
HMDB IDHMDB0061916
Secondary Accession Numbers
  • HMDB61916
Metabolite Identification
Common NamePhenylglyoxal
DescriptionPhenylglyoxal belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. Phenylglyoxal was first prepared by thermal decomposition of the sulfite derivative of the oxime:C6H5C(O)CH(NOSO2H) + 2 H2O → C6H5C(O)CHO + NH4HSO4More conveniently, it can be prepared from methyl benzoate by reaction with KCH2S(O)CH3 to give PhC(O)CH(SCH3)(OH), which is oxidized with copper(II) acetate. It has been used as a reagent to modify the amino acid, arginine. Phenylglyoxal is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylglyoxal is the organic compound with the formula C6H5C(O)C(O)H. Phenylglyoxal exists in all living organisms, ranging from bacteria to humans. It is yellow liquid when anhydrous but readily forms a colorless crystalline hydrate. Upon heating, this polymer "cracks" to give back the yellow aldehyde. It contains both an aldehyde and a ketone functional group. Dissolution of phenylglyoxal in water gives crystals of the hydrate: C6H5C(O)COH + H2O → C6H5C(O)CH(OH)2Upon heating, the hydrate loses water and regenerates the anhydrous liquid. Alternatively, it can also be prepared by oxidation of acetophenone with selenium dioxide. It has also been used to attach chemical payload (probes) to the amino acid citrulline and to peptides/proteins. Like some other aldehydes, phenylglyoxal polymerizes upon standing, as indicated by solidification of the liquid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061916 (Phenylglyoxal)

Structure #1
  Mrv0541 02241207342D          

 10 10  0  0  0  0            999 V2000
    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
    1.4289    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  7  2  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for HMDB0061916 (Phenylglyoxal)

HMDB0061916
     RDKit          3D
Phenylglyoxal
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.7927    1.4684    0.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    0.2379    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746   -0.6495    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -1.9049    0.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974   -0.2624    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6073   -1.2456    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324   -0.9665   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443    0.3382   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    1.3295   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650    1.0244    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8819   -0.1557    0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2947   -2.2724    0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794   -1.7470   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    0.5752   -0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    2.3890   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    1.8411    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
M  END
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3D SDF for HMDB0061916 (Phenylglyoxal)

Structure #1
  Mrv0541 02241207342D          

 10 10  0  0  0  0            999 V2000
    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
    1.4289    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  7  2  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061916

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H

> <INCHI_KEY>
OJUGVDODNPJEEC-UHFFFAOYSA-N

> <FORMULA>
C8H6O2

> <MOLECULAR_WEIGHT>
134.132

> <EXACT_MASS>
134.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.087242706000838

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-2-phenylacetaldehyde

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.6205640106666668

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.321435548779409

> <JCHEM_PKA_STRONGEST_BASIC>
-7.817357972192104

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
37.3171

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylglyoxal

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0061916 (Phenylglyoxal)

HMDB0061916
     RDKit          3D
Phenylglyoxal
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.7927    1.4684    0.4425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    0.2379    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746   -0.6495    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -1.9049    0.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974   -0.2624    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6073   -1.2456    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324   -0.9665   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443    0.3382   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185    1.3295   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650    1.0244    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8819   -0.1557    0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2947   -2.2724    0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794   -1.7470   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3843    0.5752   -0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    2.3890   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508    1.8411    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
M  END
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PDB for HMDB0061916 (Phenylglyoxal)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    8    9                                                       
CONECT    7    4    5    8                                                  
CONECT    8    6    7   10                                                  
CONECT    9    6                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0061916 (Phenylglyoxal)

COMPND    HMDB0061916
HETATM    1  O1  UNL     1       2.793   1.468   0.442  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.874   0.238   0.529  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.775  -0.649   0.425  1.00  0.00           C  
HETATM    4  O2  UNL     1       2.015  -1.905   0.536  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.397  -0.262   0.205  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.607  -1.246   0.121  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.932  -0.966  -0.086  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.344   0.338  -0.224  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.419   1.330  -0.152  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.065   1.024   0.061  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.882  -0.156   0.697  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.295  -2.272   0.227  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.679  -1.747  -0.145  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.384   0.575  -0.387  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.660   2.389  -0.250  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.651   1.841   0.113  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4    5
CONECT    5    6    6   10
CONECT    6    7   12
CONECT    7    8    8   13
CONECT    8    9   14
CONECT    9   10   10   15
CONECT   10   16
END
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SMILES for HMDB0061916 (Phenylglyoxal)

O=CC(=O)C1=CC=CC=C1
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INCHI for HMDB0061916 (Phenylglyoxal)

InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H
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Synonyms
ValueSource
PhenylglyoxalMeSH
Chemical FormulaC8H6O2
Average Molecular Weight134.132
Monoisotopic Molecular Weight134.036779436
IUPAC Name2-oxo-2-phenylacetaldehyde
Traditional Namephenylglyoxal
CAS Registry NumberNot Available
SMILES
O=CC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H
InChI KeyOJUGVDODNPJEEC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Aryl ketone
  • Benzoyl
  • Alpha-ketoaldehyde
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylglyoxal
METLIN IDNot Available
PubChem Compound14090
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available