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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:27:19 UTC

Update Date

2021-09-26 22:59:35 UTC

HMDB ID

HMDB0248991

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzilic acid

Description

benzilic acid, also known as benzilsaeure or a-phenylmandelate, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white crystalline aromatic acid, soluble in many primary alcohols. Benzilic acid is used in the manufacture of glycollate pharmaceuticals including Clidinium, Dilantin, and Flutropium, which are antagonists of the muscarinic acetylcholine receptors. Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde, to benzil, which is transformed to the product by the benzilic acid rearrangement reaction. Benzilic acid can be prepared by heating mixture of benzil, ethanol and potassium hydroxide. benzilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzilic acid is an organic compound with formula C14H12O3 or (C6H5)2(HO)C(COOH). It is used in manufacture of the incapacitating agent 3-quinuclidinyl benzilate (BZ) and is regulated by the Chemical Weapons Convention. It is also monitored by law enforcement agencies of many countries, because of its use in the manufacture in hallucinogenic drugs. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzilic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzilic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0248991
     RDKit          3D
Benzilic acid
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.0670   -1.6398    2.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463   -0.3775    2.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2873    0.2520    3.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.4339    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    1.7888    1.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    0.2037    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2045   -0.5350    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4187   -0.7467    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159   -0.2103   -1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133    0.5261   -1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    0.7315   -1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2467    0.0475    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136   -1.2313   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -1.5019   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5439   -0.5191   -1.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    0.7647   -0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    1.0164   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152    0.3963    4.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    2.3295    0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241   -0.9774    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104   -1.3295    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -0.3971   -1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    0.9518   -2.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    1.3302   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353   -2.0143   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8673   -2.5090   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4318   -0.7270   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767    1.5569   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    2.0665    0.0653 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  1  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
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11  6  1  0
 17 12  1  0
  3 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv0541 05031419122D          

 17 18  0  0  0  0            999 V2000
    3.1895    2.0625    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
    2.7770    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.3480    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.3480    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    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
   -0.1105    2.0625    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
   -0.5230    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248991

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16)

> <INCHI_KEY>
UKXSKSHDVLQNKG-UHFFFAOYSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.2433

> <EXACT_MASS>
228.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.308464332151917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2,2-diphenylacetic acid

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.5575470879999997

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.580328802725877

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.699661448456573

> <JCHEM_PKA_STRONGEST_BASIC>
-4.52200709266473

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
63.48210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzilic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248991
     RDKit          3D
Benzilic acid
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.0670   -1.6398    2.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463   -0.3775    2.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2873    0.2520    3.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.4339    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    1.7888    1.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    0.2037    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2045   -0.5350    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4187   -0.7467    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159   -0.2103   -1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133    0.5261   -1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    0.7315   -1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2467    0.0475    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136   -1.2313   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -1.5019   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5439   -0.5191   -1.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    0.7647   -0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    1.0164   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152    0.3963    4.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    2.3295    0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241   -0.9774    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104   -1.3295    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -0.3971   -1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    0.9518   -2.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    1.3302   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353   -2.0143   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8673   -2.5090   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4318   -0.7270   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767    1.5569   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    2.0665    0.0653 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  1  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
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11  6  1  0
 17 12  1  0
  3 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6   12                                                       
CONECT   11    7    8   14                                                  
CONECT   12    9   10   14                                                  
CONECT   13   14   15   16                                                  
CONECT   14   11   12   13   17                                             
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0248991
HETATM    1  O1  UNL     1      -0.067  -1.640   2.118  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.146  -0.377   2.190  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.287   0.252   3.406  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.084   0.434   0.922  1.00  0.00           C  
HETATM    5  O3  UNL     1      -0.225   1.789   1.288  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.202   0.204   0.234  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.205  -0.535   0.811  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.419  -0.747   0.144  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.616  -0.210  -1.106  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.613   0.526  -1.678  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.416   0.731  -1.014  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.247   0.048   0.127  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.514  -1.231  -0.300  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.642  -1.502  -1.049  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.544  -0.519  -1.401  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.289   0.765  -0.980  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.153   1.016  -0.231  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.515   0.396   4.003  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.043   2.329   0.509  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.124  -0.977   1.774  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.210  -1.329   0.599  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.569  -0.397  -1.589  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.763   0.952  -2.664  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.636   1.330  -1.510  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.835  -2.014  -0.046  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.867  -2.509  -1.395  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.432  -0.727  -1.989  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.977   1.557  -1.240  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.023   2.067   0.065  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5    6   12
CONECT    5   19
CONECT    6    7    7   11
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   24
CONECT   12   13   13   17
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   16   27
CONECT   16   17   17   28
CONECT   17   29
END

HMDB0248991
     RDKit          3D
Benzilic acid
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.0670   -1.6398    2.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463   -0.3775    2.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2873    0.2520    3.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.4339    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2249    1.7888    1.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    0.2037    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2045   -0.5350    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4187   -0.7467    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159   -0.2103   -1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133    0.5261   -1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164    0.7315   -1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2467    0.0475    0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136   -1.2313   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -1.5019   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5439   -0.5191   -1.4012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    0.7647   -0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    1.0164   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152    0.3963    4.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    2.3295    0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241   -0.9774    1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104   -1.3295    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -0.3971   -1.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    0.9518   -2.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    1.3302   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8353   -2.0143   -0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8673   -2.5090   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4318   -0.7270   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9767    1.5569   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    2.0665    0.0653 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  1  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
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11  6  1  0
 17 12  1  0
  3 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 13 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-2,2-diphenylacetic acid	ChEBI
Acide diphenylhydroxyacetique	ChEBI
alpha,alpha-Diphenyl-alpha-hydroxyacetic acid	ChEBI
alpha,alpha-Diphenylglycolic acid	ChEBI
alpha-Hydroxy-2,2-diphenylacetic acid	ChEBI
alpha-Hydroxy-alpha-phenylbenzeneacetic acid	ChEBI
alpha-Phenylmandelic acid	ChEBI
Benzilsaeure	ChEBI
Diphenylglycolic acid	ChEBI
2-Hydroxy-2,2-diphenylacetate	Generator
a,a-Diphenyl-a-hydroxyacetate	Generator
a,a-Diphenyl-a-hydroxyacetic acid	Generator
alpha,alpha-Diphenyl-alpha-hydroxyacetate	Generator
Α,α-diphenyl-α-hydroxyacetate	Generator
Α,α-diphenyl-α-hydroxyacetic acid	Generator
a,a-Diphenylglycolate	Generator
a,a-Diphenylglycolic acid	Generator
alpha,alpha-Diphenylglycolate	Generator
Α,α-diphenylglycolate	Generator
Α,α-diphenylglycolic acid	Generator
a-Hydroxy-2,2-diphenylacetate	Generator
a-Hydroxy-2,2-diphenylacetic acid	Generator
alpha-Hydroxy-2,2-diphenylacetate	Generator
Α-hydroxy-2,2-diphenylacetate	Generator
Α-hydroxy-2,2-diphenylacetic acid	Generator
a-Hydroxy-a-phenylbenzeneacetate	Generator
a-Hydroxy-a-phenylbenzeneacetic acid	Generator
alpha-Hydroxy-alpha-phenylbenzeneacetate	Generator
Α-hydroxy-α-phenylbenzeneacetate	Generator
Α-hydroxy-α-phenylbenzeneacetic acid	Generator
a-Phenylmandelate	Generator
a-Phenylmandelic acid	Generator
alpha-Phenylmandelate	Generator
Α-phenylmandelate	Generator
Α-phenylmandelic acid	Generator
Diphenylglycolate	Generator
Benzilate	Generator
DPHEAc	MeSH
2,2-Diphenyl-2-hydroxyethanoic acid	MeSH

Chemical Formula

C₁₄H₁₂O₃

Average Molecular Weight

228.2433

Monoisotopic Molecular Weight

228.07864425

IUPAC Name

2-hydroxy-2,2-diphenylacetic acid

Traditional Name

benzilic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16)

InChI Key

UKXSKSHDVLQNKG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

2-hydroxy monocarboxylic acid (CHEBI:39414 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.12	ALOGPS
logP	2.56	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.48 m³·mol⁻¹	ChemAxon
Polarizability	23.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	149.63	30932474
DeepCCS	[M-H]-	147.234	30932474
DeepCCS	[M-2H]-	180.321	30932474
DeepCCS	[M+Na]+	155.542	30932474
AllCCS	[M+H]+	152.7	32859911
AllCCS	[M+H-H2O]+	148.8	32859911
AllCCS	[M+NH4]+	156.2	32859911
AllCCS	[M+Na]+	157.2	32859911
AllCCS	[M-H]-	151.3	32859911
AllCCS	[M+Na-2H]-	151.1	32859911
AllCCS	[M+HCOO]-	151.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.9137 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1839.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	343.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	137.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	504.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	486.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1018.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	417.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1208.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	336.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	163.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	68.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzilic acid	OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1	2868.6	Standard polar	33892256
Benzilic acid	OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1	2037.9	Standard non polar	33892256
Benzilic acid	OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1	1946.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0900000000-3f167fbecb453382e628	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzilic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzilic acid 10V, Positive-QTOF	splash10-03di-0190000000-efaac40d8a455261b420	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzilic acid 20V, Positive-QTOF	splash10-01t9-5490000000-034f3edee73420aeddaa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzilic acid 40V, Positive-QTOF	splash10-004i-9100000000-2b02c41a39372f9d4258	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzilic acid 10V, Negative-QTOF	splash10-001i-0900000000-2565412c6fe1c60ab16f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzilic acid 20V, Negative-QTOF	splash10-001i-1900000000-5fe93bf8c00d775713c1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzilic acid 40V, Negative-QTOF	splash10-0a4i-1900000000-622ef9be868df501ca20	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzilic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

39414

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Benzilic acid (HMDB0248991)

MOL for HMDB0248991 (Benzilic acid)

3D MOL for HMDB0248991 (Benzilic acid)

3D SDF for HMDB0248991 (Benzilic acid)

3D-SDF for HMDB0248991 (Benzilic acid)

PDB for HMDB0248991 (Benzilic acid)

3D PDB for HMDB0248991 (Benzilic acid)

SMILES for HMDB0248991 (Benzilic acid)

INCHI for HMDB0248991 (Benzilic acid)

Structure for HMDB0248991 (Benzilic acid)

3D Structure for HMDB0248991 (Benzilic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra