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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:47:11 UTC

Update Date

2021-09-26 23:11:03 UTC

HMDB ID

HMDB0255871

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,3'-Dimethylbenzidine

Description

3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diamine, also known as 3,3'-dimethyl-4,4'-diaminobiphenyl or O-tolidine, belongs to the class of organic compounds known as 3,3'-disubstituted benzidines. These are organic compounds containing a benzidine skeleton, which is substituted only at the 3- and 3'-positions. Based on a literature review very few articles have been published on 3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,3'-dimethylbenzidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,3'-Dimethylbenzidine 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

HMDB0255871
     RDKit          3D
3,3'-Dimethylbenzidine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9273    1.8067   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9740    0.6850   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6133    0.8843   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203   -0.1471    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324    0.1076    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2007    1.2771    0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542    1.4973    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575    0.5577    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586    0.7364    0.5191 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -0.6329   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880   -1.6399   -0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482   -0.8166   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -1.4219    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6103   -1.6259    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.5884   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8963   -0.8427   -0.2029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251    1.6133   -1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861    1.9546    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3863    2.7764   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913    1.8959   -0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4778    2.0153    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9611    2.4201    1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540    0.5535    1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3730    1.0516   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -1.9470   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -2.4826    0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989   -1.1861   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847   -1.7392   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -2.2553    0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -2.6378    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5410   -0.6693    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3613   -1.2001   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15  2  1  0
 12  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
M  END


  Mrv1572004191601132D          

 16 17  0  0  0  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    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
   -2.1434   -0.4125    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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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
   -2.1434    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
   -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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  7  2  0  0  0  0
 10  2  1  0  0  0  0
 10  8  2  0  0  0  0
 11  3  2  0  0  0  0
 11  7  1  0  0  0  0
 12  4  2  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  2  0  0  0  0
 13  9  1  0  0  0  0
 14  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255871

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=CC=C1N)C1=CC=C(N)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3

> <INCHI_KEY>
NUIURNJTPRWVAP-UHFFFAOYSA-N

> <FORMULA>
C14H16N2

> <MOLECULAR_WEIGHT>
212.296

> <EXACT_MASS>
212.131348523

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.20721014286038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diamine

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
2.9894620486666668

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.581079522560741

> <JCHEM_POLAR_SURFACE_AREA>
52.04

> <JCHEM_REFRACTIVITY>
70.6774

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255871
     RDKit          3D
3,3'-Dimethylbenzidine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9273    1.8067   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9740    0.6850   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6133    0.8843   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203   -0.1471    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324    0.1076    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2007    1.2771    0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542    1.4973    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575    0.5577    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586    0.7364    0.5191 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -0.6329   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880   -1.6399   -0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482   -0.8166   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -1.4219    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6103   -1.6259    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.5884   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8963   -0.8427   -0.2029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251    1.6133   -1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861    1.9546    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3863    2.7764   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913    1.8959   -0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4778    2.0153    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9611    2.4201    1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540    0.5535    1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3730    1.0516   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -1.9470   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -2.4826    0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989   -1.1861   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847   -1.7392   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -2.2553    0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -2.6378    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5410   -0.6693    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3613   -1.2001   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15  2  1  0
 12  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.667   6.160   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    5   11                                                       
CONECT    4    6   12                                                       
CONECT    5    3   13                                                       
CONECT    6    4   14                                                       
CONECT    7    9   11                                                       
CONECT    8   10   12                                                       
CONECT    9    1    7   13                                                  
CONECT   10    2    8   14                                                  
CONECT   11    3    7   12                                                  
CONECT   12    4    8   11                                                  
CONECT   13    5    9   15                                                  
CONECT   14    6   10   16                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0255871
HETATM    1  C1  UNL     1      -3.927   1.807  -0.376  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.974   0.685  -0.168  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.613   0.884  -0.054  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.720  -0.147   0.137  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.732   0.108   0.254  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.201   1.277   0.814  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.554   1.497   0.908  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.458   0.558   0.447  1.00  0.00           C  
HETATM    9  N1  UNL     1       4.859   0.736   0.519  1.00  0.00           N  
HETATM   10  C9  UNL     1       3.011  -0.633  -0.123  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.988  -1.640  -0.618  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.648  -0.817  -0.200  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.233  -1.422   0.215  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.610  -1.626   0.100  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.499  -0.588  -0.092  1.00  0.00           C  
HETATM   16  N2  UNL     1      -4.896  -0.843  -0.203  1.00  0.00           N  
HETATM   17  H1  UNL     1      -4.625   1.613  -1.214  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.486   1.955   0.571  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.386   2.776  -0.546  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.191   1.896  -0.115  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.478   2.015   1.176  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.961   2.420   1.349  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.354   0.554   1.405  1.00  0.00           H  
HETATM   24  H8  UNL     1       5.373   1.052  -0.325  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.763  -1.947  -1.656  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.977  -2.483   0.101  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.999  -1.186  -0.594  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.285  -1.739  -0.640  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.552  -2.255   0.367  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.023  -2.638   0.162  1.00  0.00           H  
HETATM   31  H15 UNL     1      -5.541  -0.669   0.621  1.00  0.00           H  
HETATM   32  H16 UNL     1      -5.361  -1.200  -1.063  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   15
CONECT    3    4   20
CONECT    4    5   13   13
CONECT    5    6    6   12
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   10
CONECT    9   23   24
CONECT   10   11   12   12
CONECT   11   25   26   27
CONECT   12   28
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16
CONECT   16   31   32
END

HMDB0255871
     RDKit          3D
3,3'-Dimethylbenzidine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9273    1.8067   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9740    0.6850   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6133    0.8843   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7203   -0.1471    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324    0.1076    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2007    1.2771    0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542    1.4973    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575    0.5577    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586    0.7364    0.5191 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -0.6329   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880   -1.6399   -0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482   -0.8166   -0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -1.4219    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6103   -1.6259    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.5884   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8963   -0.8427   -0.2029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251    1.6133   -1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861    1.9546    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3863    2.7764   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913    1.8959   -0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4778    2.0153    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9611    2.4201    1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540    0.5535    1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3730    1.0516   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -1.9470   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -2.4826    0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989   -1.1861   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2847   -1.7392   -0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -2.2553    0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -2.6378    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5410   -0.6693    0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3613   -1.2001   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15  2  1  0
 12  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3'-Dimethyl-4,4'-diaminobiphenyl	Kegg
O-Tolidine	Kegg
2-Tolidine	MeSH
2-Tolidine dihydrochloride	MeSH
2-Tolidine dihydrofluoride	MeSH
2-Tolidine hexahydrofluoride	MeSH
2-Tolidine perchlorate	MeSH
2-Tolidine perchlorate (1-)	MeSH
2-Tolidine tetrahydrofluoride	MeSH
3,3'-Dimethylbenzidine	MeSH
Tolidine blue	MeSH

Chemical Formula

C₁₄H₁₆N₂

Average Molecular Weight

212.296

Monoisotopic Molecular Weight

212.131348523

IUPAC Name

3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diamine

Traditional Name

3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diamine

CAS Registry Number

Not Available

SMILES

CC1=CC(=CC=C1N)C1=CC=C(N)C(C)=C1

InChI Identifier

InChI=1S/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3

InChI Key

NUIURNJTPRWVAP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3,3'-disubstituted benzidines. These are organic compounds containing a benzidine skeleton, which is substituted only at the 3- and 3'-positions.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

3,3'-disubstituted benzidines

Alternative Parents

Substituents

3,3'-disubstituted benzidine
Aminotoluene
Aniline or substituted anilines
Toluene
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

biphenyls (CHEBI:34320 )

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	2.44	ALOGPS
logP	2.99	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	4.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.04 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.68 m³·mol⁻¹	ChemAxon
Polarizability	25.21 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]+	156.853	30932474
DeepCCS	[M-H]-	154.462	30932474
DeepCCS	[M-2H]-	187.375	30932474
DeepCCS	[M+Na]+	162.913	30932474
AllCCS	[M+H]+	148.2	32859911
AllCCS	[M+H-H2O]+	144.0	32859911
AllCCS	[M+NH4]+	152.2	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	153.6	32859911
AllCCS	[M+Na-2H]-	153.7	32859911
AllCCS	[M+HCOO]-	153.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3147 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1314.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	280.5 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	340.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1032.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	284.4 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	608.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	303.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	225.6 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	72.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Dimethylbenzidine	CC1=CC(=CC=C1N)C1=CC=C(N)C(C)=C1	3240.8	Standard polar	33892256
3,3'-Dimethylbenzidine	CC1=CC(=CC=C1N)C1=CC=C(N)C(C)=C1	2215.6	Standard non polar	33892256
3,3'-Dimethylbenzidine	CC1=CC(=CC=C1N)C1=CC=C(N)C(C)=C1	2313.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Dimethylbenzidine,1TMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C)C(C)=C2)=CC=C1N	2474.6	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,1TMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C)C(C)=C2)=CC=C1N	2442.0	Standard non polar	33892256
3,3'-Dimethylbenzidine,1TMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C)C(C)=C2)=CC=C1N	2963.4	Standard polar	33892256
3,3'-Dimethylbenzidine,2TMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C	2556.9	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,2TMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C	2537.9	Standard non polar	33892256
3,3'-Dimethylbenzidine,2TMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C	2628.8	Standard polar	33892256
3,3'-Dimethylbenzidine,2TMS,isomer #2	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N	2474.1	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,2TMS,isomer #2	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N	2485.1	Standard non polar	33892256
3,3'-Dimethylbenzidine,2TMS,isomer #2	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N	2856.2	Standard polar	33892256
3,3'-Dimethylbenzidine,3TMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C	2544.7	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,3TMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C	2591.5	Standard non polar	33892256
3,3'-Dimethylbenzidine,3TMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C	2568.7	Standard polar	33892256
3,3'-Dimethylbenzidine,4TMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2569.4	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,4TMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2704.7	Standard non polar	33892256
3,3'-Dimethylbenzidine,4TMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C)=C2)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2476.8	Standard polar	33892256
3,3'-Dimethylbenzidine,1TBDMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N	2761.8	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,1TBDMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N	2682.0	Standard non polar	33892256
3,3'-Dimethylbenzidine,1TBDMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N	3048.1	Standard polar	33892256
3,3'-Dimethylbenzidine,2TBDMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3098.2	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,2TBDMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3018.5	Standard non polar	33892256
3,3'-Dimethylbenzidine,2TBDMS,isomer #1	CC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	2855.3	Standard polar	33892256
3,3'-Dimethylbenzidine,2TBDMS,isomer #2	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N	2954.0	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,2TBDMS,isomer #2	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N	2926.6	Standard non polar	33892256
3,3'-Dimethylbenzidine,2TBDMS,isomer #2	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N	2989.5	Standard polar	33892256
3,3'-Dimethylbenzidine,3TBDMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3259.5	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,3TBDMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3266.1	Standard non polar	33892256
3,3'-Dimethylbenzidine,3TBDMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	2892.9	Standard polar	33892256
3,3'-Dimethylbenzidine,4TBDMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3482.7	Semi standard non polar	33892256
3,3'-Dimethylbenzidine,4TBDMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3535.1	Standard non polar	33892256
3,3'-Dimethylbenzidine,4TBDMS,isomer #1	CC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)=C2)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2872.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dimethylbenzidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2790000000-fd7cfac347210206ffed	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dimethylbenzidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 50V, Positive-QTOF	splash10-001i-0900000000-36b5f21038f913d97891	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 30V, Positive-QTOF	splash10-03ea-0950000000-f950501bc39d72fddee9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 40V, Positive-QTOF	splash10-001i-0900000000-10cfdfff3f1e0bfd084e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 30V, Positive-QTOF	splash10-03ea-0950000000-452cec65443da2c5d420	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 40V, Positive-QTOF	splash10-001i-0900000000-64bbbdbdf004b06bceb0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 20V, Positive-QTOF	splash10-03di-0390000000-eeb5b464aafb68b4abca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 10V, Positive-QTOF	splash10-03di-0090000000-9c82589c480820333127	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 10V, Positive-QTOF	splash10-03dj-0690000000-128797423919dbbdd80f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 20V, Positive-QTOF	splash10-03dj-0970000000-4caa9bfeefa11e50880b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 40V, Positive-QTOF	splash10-014i-2900000000-78f1cab0c542f6c33359	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 10V, Negative-QTOF	splash10-03di-0090000000-4eba96dea15385a141d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 20V, Negative-QTOF	splash10-03di-0190000000-dca4b4b20f95ce6f9bc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethylbenzidine 40V, Negative-QTOF	splash10-03dm-3930000000-661894eecbaa246cc298	2016-08-03	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

8106

KEGG Compound ID

C14443

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8413

PDB ID

Not Available

ChEBI ID

Not Available

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 3,3'-Dimethylbenzidine (HMDB0255871)

MOL for HMDB0255871 (3,3'-Dimethylbenzidine)

3D MOL for HMDB0255871 (3,3'-Dimethylbenzidine)

3D SDF for HMDB0255871 (3,3'-Dimethylbenzidine)

3D-SDF for HMDB0255871 (3,3'-Dimethylbenzidine)

PDB for HMDB0255871 (3,3'-Dimethylbenzidine)

3D PDB for HMDB0255871 (3,3'-Dimethylbenzidine)

SMILES for HMDB0255871 (3,3'-Dimethylbenzidine)

INCHI for HMDB0255871 (3,3'-Dimethylbenzidine)

Structure for HMDB0255871 (3,3'-Dimethylbenzidine)

3D Structure for HMDB0255871 (3,3'-Dimethylbenzidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra