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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:27:21 UTC

Update Date

2021-09-26 22:51:56 UTC

HMDB ID

HMDB0244288

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4,4'-Methylenebis(2-chloroaniline)

Description

4,4'-Methylenebis(2-chloroaniline), also known as MOCA, 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. 4,4'-Methylenebis(2-chloroaniline) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4,4'-Methylenebis(2-chloroaniline) is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a small amount of articles have been published on 4,4'-Methylenebis(2-chloroaniline). This compound has been identified in human blood as reported by (PMID: 31557052 ). 4,4'-methylenebis(2-chloroaniline) is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4,4'-Methylenebis(2-chloroaniline) 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

HMDB0244288
     RDKit          3D
4,4'-Methylenebis(2-chloroaniline)
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.6526    0.7428    1.5231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.3276    0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843   -0.8619    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -1.2519    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2939   -0.4690   -0.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136   -0.9663   -1.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632   -0.5340   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755   -1.3083    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920   -0.9490    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128    0.2224    0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.6202    0.8072 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    0.9870   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8051    2.4792   -1.1886 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7753    0.6305   -1.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    0.7047   -0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.1093   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257    2.6346   -0.6273 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5918    1.6107    2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5163    0.1881    1.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.4859    1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209   -2.1994    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -2.0523   -1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1870   -0.5308   -2.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -2.2429    0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -1.5599    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940   -0.0782    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948    1.6137    1.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    1.2799   -2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    1.3391   -1.7977 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 16  2  1  0
 14  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
M  END


  Mrv0541 02241204182D          

 17 18  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 N   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    0.7145   -1.2375    0.0000 Cl  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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244288

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2

> <INCHI_KEY>
IBOFVQJTBBUKMU-UHFFFAOYSA-N

> <FORMULA>
C13H12Cl2N2

> <MOLECULAR_WEIGHT>
267.154

> <EXACT_MASS>
266.037753808

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.738569721264057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
3.6152772876666663

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.0975125919051716

> <JCHEM_POLAR_SURFACE_AREA>
52.04

> <JCHEM_REFRACTIVITY>
74.80560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bis amine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244288
     RDKit          3D
4,4'-Methylenebis(2-chloroaniline)
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.6526    0.7428    1.5231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.3276    0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843   -0.8619    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -1.2519    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2939   -0.4690   -0.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136   -0.9663   -1.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632   -0.5340   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755   -1.3083    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920   -0.9490    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128    0.2224    0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.6202    0.8072 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    0.9870   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8051    2.4792   -1.1886 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7753    0.6305   -1.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    0.7047   -0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.1093   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257    2.6346   -0.6273 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5918    1.6107    2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5163    0.1881    1.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.4859    1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209   -2.1994    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -2.0523   -1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1870   -0.5308   -2.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -2.2429    0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -1.5599    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940   -0.0782    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948    1.6137    1.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    1.2799   -2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    1.3391   -1.7977 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 16  2  1  0
 14  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.334 -10.010   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7                                                       
CONECT   15    5   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0244288
HETATM    1  N1  UNL     1      -4.653   0.743   1.523  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.518   0.328   0.765  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.884  -0.862   1.038  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.782  -1.252   0.292  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.294  -0.469  -0.735  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.114  -0.966  -1.476  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.163  -0.534  -0.905  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.776  -1.308   0.048  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.992  -0.949   0.628  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.613   0.222   0.241  1.00  0.00           C  
HETATM   11  N2  UNL     1       4.848   0.620   0.807  1.00  0.00           N  
HETATM   12  C10 UNL     1       2.976   0.987  -0.721  1.00  0.00           C  
HETATM   13 CL1  UNL     1       3.805   2.479  -1.189  1.00  0.00          CL  
HETATM   14  C11 UNL     1       1.775   0.630  -1.293  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.924   0.705  -1.000  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.021   1.109  -0.269  1.00  0.00           C  
HETATM   17 CL2  UNL     1      -3.826   2.635  -0.627  1.00  0.00          CL  
HETATM   18  H1  UNL     1      -4.592   1.611   2.084  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.516   0.188   1.512  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.264  -1.486   1.848  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.321  -2.199   0.551  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.223  -2.052  -1.598  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.187  -0.531  -2.507  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.356  -2.243   0.408  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.472  -1.560   1.377  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.594  -0.078   0.977  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.995   1.614   1.048  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.320   1.280  -2.052  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.565   1.339  -1.798  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3    3   16
CONECT    3    4   20
CONECT    4    5    5   21
CONECT    5    6   15
CONECT    6    7   22   23
CONECT    7    8    8   14
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   12
CONECT   11   26   27
CONECT   12   13   14   14
CONECT   14   28
CONECT   15   16   16   29
CONECT   16   17
END

HMDB0244288
     RDKit          3D
4,4'-Methylenebis(2-chloroaniline)
 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.6526    0.7428    1.5231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.3276    0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843   -0.8619    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -1.2519    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2939   -0.4690   -0.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136   -0.9663   -1.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632   -0.5340   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755   -1.3083    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920   -0.9490    0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128    0.2224    0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8479    0.6202    0.8072 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762    0.9870   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8051    2.4792   -1.1886 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7753    0.6305   -1.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    0.7047   -0.9998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.1093   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8257    2.6346   -0.6273 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5918    1.6107    2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5163    0.1881    1.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.4859    1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209   -2.1994    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -2.0523   -1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1870   -0.5308   -2.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -2.2429    0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -1.5599    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940   -0.0782    0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948    1.6137    1.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3199    1.2799   -2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649    1.3391   -1.7977 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 16  2  1  0
 14  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methylenebis(chloroaniline)	ChEBI
MOCA	ChEBI
3,3'-Dichloro-4,4'-diaminodiphenylmethane	HMDB
Methylene bis(chloroaniline)	HMDB
MBOCA	HMDB

Chemical Formula

C₁₃H₁₂Cl₂N₂

Average Molecular Weight

267.154

Monoisotopic Molecular Weight

266.037753808

IUPAC Name

4-[(4-amino-3-chlorophenyl)methyl]-2-chloroaniline

Traditional Name

bis amine

CAS Registry Number

Not Available

SMILES

NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl

InChI Identifier

InChI=1S/C13H12Cl2N2/c14-10-6-8(1-3-12(10)16)5-9-2-4-13(17)11(15)7-9/h1-4,6-7H,5,16-17H2

InChI Key

IBOFVQJTBBUKMU-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
Aniline or substituted anilines
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

chloroaniline (CHEBI:28124 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0244288)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Biological role

Metabolite (HMDB: HMDB0244288)

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	3.72	ALOGPS
logP	3.62	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	3.1	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	2	ChemAxon
Refractivity	74.81 m³·mol⁻¹	ChemAxon
Polarizability	26.74 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]+	158.754	30932474
DeepCCS	[M-H]-	156.396	30932474
DeepCCS	[M-2H]-	189.329	30932474
DeepCCS	[M+Na]+	164.847	30932474
AllCCS	[M+H]+	157.6	32859911
AllCCS	[M+H-H2O]+	153.7	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.2	32859911
AllCCS	[M-H]-	155.4	32859911
AllCCS	[M+Na-2H]-	155.3	32859911
AllCCS	[M+HCOO]-	155.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.04 minutes	32390414
Predicted by Siyang on May 30, 2022	14.9911 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1764.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	490.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	158.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	320.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	453.5 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	491.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	158.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1404.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	424.4 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	1157.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	444.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	385.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	71.7 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	19.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,4'-Methylenebis(2-chloroaniline)	NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	3689.8	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline)	NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	2442.1	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline)	NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	2473.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,4'-Methylenebis(2-chloroaniline),1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	2555.8	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	2428.0	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),1TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	3278.2	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C(Cl)=C2)C=C1Cl	2633.1	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C(Cl)=C2)C=C1Cl	2443.1	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C)C(Cl)=C2)C=C1Cl	2841.5	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C	2466.8	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C	2525.2	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C	3061.0	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl	2552.5	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl	2492.6	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),3TMS,isomer #1	C[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl	2699.8	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C	2512.3	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C	2551.1	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),4TMS,isomer #1	C[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C	2539.3	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	2756.4	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	2666.7	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl	3325.6	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl	3038.8	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl	2927.5	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl	3031.5	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C	2903.4	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C	2930.7	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C	3137.6	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl	3187.9	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl	3107.5	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl	2986.3	Standard polar	33892256
4,4'-Methylenebis(2-chloroaniline),4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C	3369.3	Semi standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C	3277.9	Standard non polar	33892256
4,4'-Methylenebis(2-chloroaniline),4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C(CC2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(Cl)=C2)C=C1Cl)[Si](C)(C)C(C)(C)C	2908.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-0890000000-d320fad1a29793ad1cd3	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0159-2690000000-cb107296d1f635b2a12a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Positive-QTOF	splash10-014i-0090000000-ac6db8aa96928a715ff0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Positive-QTOF	splash10-014i-0390000000-5200973976fe40d343c8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Positive-QTOF	splash10-0h93-0790000000-9bffe8b198bbfea28e82	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Negative-QTOF	splash10-014i-0090000000-a39ca28199798c1d03b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Negative-QTOF	splash10-014i-0090000000-ea98e6716aef094aff27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Negative-QTOF	splash10-016r-2590000000-6da5025dcc24706340ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Positive-QTOF	splash10-014i-0090000000-56429813ec6e144d5baa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Positive-QTOF	splash10-014i-0090000000-388bf1eeaceec6102241	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Positive-QTOF	splash10-0002-0950000000-0208d8e66ffecbcf4b9e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 10V, Negative-QTOF	splash10-014i-3090000000-685f6029d831cae1342b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 20V, Negative-QTOF	splash10-0159-6090000000-189ae8cf88e4d83e80f0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4'-Methylenebis(2-chloroaniline) 40V, Negative-QTOF	splash10-001i-9110000000-6f3606859a73a43fab2c	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

7262

KEGG Compound ID

C10999

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4,4'-Methylenebis(2-chloroaniline)

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28124

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1330971

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 4,4'-Methylenebis(2-chloroaniline) (HMDB0244288)

MOL for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

3D MOL for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

3D SDF for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

3D-SDF for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

PDB for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

3D PDB for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

SMILES for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

INCHI for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

Structure for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

3D Structure for HMDB0244288 (4,4'-Methylenebis(2-chloroaniline))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra