Showing metabocard for Phenylglyoxal (MMDBc0030207)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:58:24 UTC
Update Date2022-08-31 17:40:41 UTC
Metabolite IDMMDBc0030207
Metabolite Identification
Common NamePhenylglyoxal
DescriptionPhenylglyoxal is a member of the chemical class known as Phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. It contains both an aldehyde and a ketone functional group. It is yellow liquid when anhydrous but readily forms a colorless crystalline hydrate. It has been used as a reagent to modify the amino acid, arginine. It is a substrate for the enzyme HcHA or Glyoxylse III. This enzyme catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate and generate phenylactate.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005634c2c08968>

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 #<Metabolite:0x00005634c2c08968>

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 #<Metabolite:0x00005634c2c08968>

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>
MMDBc0030207

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00005634c2c08968>

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 #<Metabolite:0x00005634c2c08968>

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 #<Metabolite:0x00005634c2c08968>

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 #<Metabolite:0x00005634c2c08968>

O=CC(=O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x00005634c2c08968>

InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H
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Synonyms
ValueSource
PhenylglyoxalMeSH
Molecular FormulaC8H6O2
Average Mass134.132
Monoisotopic Mass134.036779436
IUPAC Name2-oxo-2-phenylacetaldehyde
Traditional Namephenylglyoxal
CAS Registry Number1074-12-0
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