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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:02:48 UTC

Update Date

2021-09-26 22:54:48 UTC

HMDB ID

HMDB0246003

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,3'-Dimethoxybenzidine

Description

3,3'-dimethoxy-[1,1'-biphenyl]-4,4'-diamine, also known as ortho-dianisidine, 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'-dimethoxy-[1,1'-biphenyl]-4,4'-diamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3,3'-dimethoxybenzidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3,3'-Dimethoxybenzidine 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

HMDB0246003
     RDKit          3D
3,3'-Dimethoxybenzidine
 34 35  0  0  0  0  0  0  0  0999 V2000
    3.5416   -0.1348   -2.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160    0.4220   -0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    0.5416    0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.1323   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637    0.2733    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096   -0.1587    0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313   -0.6133    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443   -1.0405    1.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -1.0065    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7824   -1.4530    0.2545 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386   -0.5583   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703   -0.5431   -1.9712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -0.1180   -3.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -0.1433   -0.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    0.8373    2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651    1.2485    2.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2217    1.1106    1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    1.5342    1.5110 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9203   -1.0468   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031    0.5741   -2.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -0.5032   -2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -0.3116   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.6575    2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056   -1.3953    2.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4412   -1.3237    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341   -1.9126   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980    0.9399   -3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -0.2217   -3.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742   -0.7270   -4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    0.2147   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005    0.9382    2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489    1.6911    3.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7691    2.2333    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3627    1.1778    0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 14  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
M  END


  Mrv0541 05041402362D          

 18 19  0  0  0  0            999 V2000
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    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
   -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
   -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    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
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17  1  1  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246003

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(N)C=CC(=C1)C1=CC(OC)=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O2/c1-17-13-7-9(3-5-11(13)15)10-4-6-12(16)14(8-10)18-2/h3-8H,15-16H2,1-2H3

> <INCHI_KEY>
JRBJSXQPQWSCCF-UHFFFAOYSA-N

> <FORMULA>
C14H16N2O2

> <MOLECULAR_WEIGHT>
244.289

> <EXACT_MASS>
244.121177766

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.911792923675932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(4-amino-3-methoxyphenyl)-2-methoxyaniline

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.6472767386666662

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.554770199550598

> <JCHEM_POLAR_SURFACE_AREA>
70.5

> <JCHEM_REFRACTIVITY>
73.52140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dianisidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246003
     RDKit          3D
3,3'-Dimethoxybenzidine
 34 35  0  0  0  0  0  0  0  0999 V2000
    3.5416   -0.1348   -2.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160    0.4220   -0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    0.5416    0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.1323   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637    0.2733    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096   -0.1587    0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313   -0.6133    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443   -1.0405    1.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -1.0065    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7824   -1.4530    0.2545 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386   -0.5583   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703   -0.5431   -1.9712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -0.1180   -3.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -0.1433   -0.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    0.8373    2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651    1.2485    2.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2217    1.1106    1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    1.5342    1.5110 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9203   -1.0468   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031    0.5741   -2.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -0.5032   -2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -0.3116   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.6575    2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056   -1.3953    2.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4412   -1.3237    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341   -1.9126   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980    0.9399   -3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -0.2217   -3.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742   -0.7270   -4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    0.2147   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005    0.9382    2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489    1.6911    3.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7691    2.2333    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3627    1.1778    0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 14  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3    5    9                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   12                                                       
CONECT    7    9   13                                                       
CONECT    8   10   14                                                       
CONECT    9    3    7   10                                                  
CONECT   10    4    8    9                                                  
CONECT   11    5   13   15                                                  
CONECT   12    6   14   16                                                  
CONECT   13    7   11   17                                                  
CONECT   14    8   12   18                                                  
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17    1   13                                                       
CONECT   18    2   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0246003
HETATM    1  C1  UNL     1       3.542  -0.135  -2.132  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.816   0.422  -0.874  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.829   0.542   0.079  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.528   0.132  -0.128  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.564   0.273   0.867  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.810  -0.159   0.651  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.531  -0.613   1.733  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.844  -1.041   1.600  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.433  -1.006   0.353  1.00  0.00           C  
HETATM   10  N1  UNL     1      -4.782  -1.453   0.255  1.00  0.00           N  
HETATM   11  C9  UNL     1      -2.739  -0.558  -0.746  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.370  -0.543  -1.971  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.802  -0.118  -3.177  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.438  -0.143  -0.570  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.967   0.837   2.060  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.265   1.249   2.273  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.222   1.111   1.292  1.00  0.00           C  
HETATM   18  N2  UNL     1       4.561   1.534   1.511  1.00  0.00           N  
HETATM   19  H1  UNL     1       2.920  -1.047  -1.969  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.003   0.574  -2.803  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.461  -0.503  -2.644  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.239  -0.312  -1.086  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.107  -0.657   2.732  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.406  -1.395   2.443  1.00  0.00           H  
HETATM   25  H7  UNL     1      -5.441  -1.324   1.063  1.00  0.00           H  
HETATM   26  H8  UNL     1      -5.134  -1.913  -0.617  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.098   0.940  -3.426  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.716  -0.222  -3.226  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.274  -0.727  -4.002  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.872   0.215  -1.426  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.200   0.938   2.821  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.549   1.691   3.233  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.769   2.233   2.256  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.363   1.178   0.957  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   22
CONECT    5    6   15   15
CONECT    6    7    7   14
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   11
CONECT   10   25   26
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   27   28   29
CONECT   14   30
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   33   34
END

HMDB0246003
     RDKit          3D
3,3'-Dimethoxybenzidine
 34 35  0  0  0  0  0  0  0  0999 V2000
    3.5416   -0.1348   -2.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8160    0.4220   -0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    0.5416    0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284    0.1323   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5637    0.2733    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096   -0.1587    0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313   -0.6133    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443   -1.0405    1.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -1.0065    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7824   -1.4530    0.2545 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386   -0.5583   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703   -0.5431   -1.9712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -0.1180   -3.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -0.1433   -0.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    0.8373    2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651    1.2485    2.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2217    1.1106    1.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610    1.5342    1.5110 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9203   -1.0468   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031    0.5741   -2.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -0.5032   -2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -0.3116   -1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.6575    2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056   -1.3953    2.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4412   -1.3237    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341   -1.9126   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980    0.9399   -3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -0.2217   -3.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742   -0.7270   -4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8718    0.2147   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005    0.9382    2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489    1.6911    3.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7691    2.2333    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3627    1.1778    0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 14  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ortho-dianisidine	Kegg
Dianisidine	MeSH
Dianisidine dihydrochloride	MeSH
Hydrochloride, dianisidine	MeSH
O-Dianisidine	MeSH
3,3' Dimethoxybenzidine	MeSH
Dianisidine hydrochloride	MeSH
Sulfate, dianisidine	MeSH
Dianisidine sulfate	MeSH
Dihydrochloride, dianisidine	MeSH
O Dianisidine	MeSH

Chemical Formula

C₁₄H₁₆N₂O₂

Average Molecular Weight

244.289

Monoisotopic Molecular Weight

244.121177766

IUPAC Name

4-(4-amino-3-methoxyphenyl)-2-methoxyaniline

Traditional Name

dianisidine

CAS Registry Number

Not Available

SMILES

COC1=C(N)C=CC(=C1)C1=CC(OC)=C(N)C=C1

InChI Identifier

InChI=1S/C14H16N2O2/c1-17-13-7-9(3-5-11(13)15)10-4-6-12(16)14(8-10)18-2/h3-8H,15-16H2,1-2H3

InChI Key

JRBJSXQPQWSCCF-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
Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Phenol ether
Aniline or substituted anilines
Methoxybenzene
Alkyl aryl ether
Ether
Primary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

biphenyls (CHEBI:82321 )
a small molecule (CPD0-1477 )

Ontology

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	2.02	ALOGPS
logP	1.65	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	4.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.5 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.52 m³·mol⁻¹	ChemAxon
Polarizability	26.91 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]+	166.624	30932474
DeepCCS	[M-H]-	164.266	30932474
DeepCCS	[M-2H]-	197.152	30932474
DeepCCS	[M+Na]+	172.717	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	160.5	32859911
AllCCS	[M+Na]+	161.6	32859911
AllCCS	[M-H]-	159.7	32859911
AllCCS	[M+Na-2H]-	159.7	32859911
AllCCS	[M+HCOO]-	159.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Dimethoxybenzidine	COC1=C(N)C=CC(=C1)C1=CC(OC)=C(N)C=C1	3502.0	Standard polar	33892256
3,3'-Dimethoxybenzidine	COC1=C(N)C=CC(=C1)C1=CC(OC)=C(N)C=C1	2374.5	Standard non polar	33892256
3,3'-Dimethoxybenzidine	COC1=C(N)C=CC(=C1)C1=CC(OC)=C(N)C=C1	2524.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Dimethoxybenzidine,1TMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C)C(OC)=C2)=CC=C1N	2661.4	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,1TMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C)C(OC)=C2)=CC=C1N	2596.1	Standard non polar	33892256
3,3'-Dimethoxybenzidine,1TMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C)C(OC)=C2)=CC=C1N	3536.7	Standard polar	33892256
3,3'-Dimethoxybenzidine,2TMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C	2739.5	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,2TMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C	2781.9	Standard non polar	33892256
3,3'-Dimethoxybenzidine,2TMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C	3155.4	Standard polar	33892256
3,3'-Dimethoxybenzidine,2TMS,isomer #2	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N	2600.7	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,2TMS,isomer #2	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N	2680.3	Standard non polar	33892256
3,3'-Dimethoxybenzidine,2TMS,isomer #2	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N	3292.5	Standard polar	33892256
3,3'-Dimethoxybenzidine,3TMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C	2676.9	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,3TMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C	2816.9	Standard non polar	33892256
3,3'-Dimethoxybenzidine,3TMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C	2976.0	Standard polar	33892256
3,3'-Dimethoxybenzidine,4TMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2649.5	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,4TMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2881.8	Standard non polar	33892256
3,3'-Dimethoxybenzidine,4TMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(OC)=C2)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2811.7	Standard polar	33892256
3,3'-Dimethoxybenzidine,1TBDMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N	2918.1	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,1TBDMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N	2814.2	Standard non polar	33892256
3,3'-Dimethoxybenzidine,1TBDMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N	3568.1	Standard polar	33892256
3,3'-Dimethoxybenzidine,2TBDMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3217.5	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,2TBDMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3220.7	Standard non polar	33892256
3,3'-Dimethoxybenzidine,2TBDMS,isomer #1	COC1=CC(C2=CC=C(N[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3297.4	Standard polar	33892256
3,3'-Dimethoxybenzidine,2TBDMS,isomer #2	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N	3102.1	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,2TBDMS,isomer #2	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N	3112.4	Standard non polar	33892256
3,3'-Dimethoxybenzidine,2TBDMS,isomer #2	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N	3354.0	Standard polar	33892256
3,3'-Dimethoxybenzidine,3TBDMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3354.3	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,3TBDMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3469.9	Standard non polar	33892256
3,3'-Dimethoxybenzidine,3TBDMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N[Si](C)(C)C(C)(C)C	3235.5	Standard polar	33892256
3,3'-Dimethoxybenzidine,4TBDMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3502.9	Semi standard non polar	33892256
3,3'-Dimethoxybenzidine,4TBDMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3694.0	Standard non polar	33892256
3,3'-Dimethoxybenzidine,4TBDMS,isomer #1	COC1=CC(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3157.7	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'-Dimethoxybenzidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0290000000-6c2f368a60cc2aa46449	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dimethoxybenzidine 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'-Dimethoxybenzidine 75V, Positive-QTOF	splash10-000i-0900000000-1333a5f624be8d18c6fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 90V, Positive-QTOF	splash10-000i-0900000000-c87e752c4ad6e95d4bb2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 60V, Positive-QTOF	splash10-000i-0950000000-401593244e5df19498f3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 15V, Positive-QTOF	splash10-0002-0090000000-76c8fdc90ef40061b7ba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 55V, Positive-QTOF	splash10-001i-0390000000-f94a069bc831f0cc93b1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 80V, Positive-QTOF	splash10-000i-0910000000-a6efe7b1db0b5a58a4f2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 50V, Positive-QTOF	splash10-0a4r-0900000000-d8c4ae57acfd1e07818d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 30V, Positive-QTOF	splash10-000t-0090000000-035457a2c2436dce3097	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 55V, Positive-QTOF	splash10-001i-0090000000-be51ee56a3dceab37e5c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 35V, Positive-QTOF	splash10-001i-0090000000-e7ba29d3e7fa3fce971f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 45V, Positive-QTOF	splash10-001i-0190000000-dc7e78dc2f932a4dbdcd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 40V, Positive-QTOF	splash10-000i-0910000000-8deb33a8f1d04bd854f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 30V, Positive-QTOF	splash10-0udr-0590000000-7b71d0252223f6f0a88e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 10V, Positive-QTOF	splash10-0005-0090000000-c72b307fdbd49d025527	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 20V, Positive-QTOF	splash10-001m-0090000000-43bc39af92506eb5680c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 10V, Positive-QTOF	splash10-0002-0090000000-7baf4d101a9926a6325b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 20V, Positive-QTOF	splash10-0002-0190000000-cd00e4735dd15dc6aa51	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 40V, Positive-QTOF	splash10-03ej-1930000000-26fdfa2d8770951e27a8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 10V, Negative-QTOF	splash10-0006-0090000000-e4fa9ad96d42a8354ff9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 20V, Negative-QTOF	splash10-0006-0090000000-8d74a657222d85ed49e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 40V, Negative-QTOF	splash10-0095-7970000000-c7a47fd9604c76b498ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 10V, Positive-QTOF	splash10-0002-0090000000-20e51451d2fb6fc55d16	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 20V, Positive-QTOF	splash10-01ot-0390000000-258f21c546da39c18975	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 40V, Positive-QTOF	splash10-00ed-0930000000-bb9f923cf7efa11bf325	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dimethoxybenzidine 10V, Negative-QTOF	splash10-0006-0090000000-ba98f00aedf482df562f	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

8104

KEGG Compound ID

C19231

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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'-Dimethoxybenzidine (HMDB0246003)

MOL for HMDB0246003 (3,3'-Dimethoxybenzidine)

3D MOL for HMDB0246003 (3,3'-Dimethoxybenzidine)

3D SDF for HMDB0246003 (3,3'-Dimethoxybenzidine)

3D-SDF for HMDB0246003 (3,3'-Dimethoxybenzidine)

PDB for HMDB0246003 (3,3'-Dimethoxybenzidine)

3D PDB for HMDB0246003 (3,3'-Dimethoxybenzidine)

SMILES for HMDB0246003 (3,3'-Dimethoxybenzidine)

INCHI for HMDB0246003 (3,3'-Dimethoxybenzidine)

Structure for HMDB0246003 (3,3'-Dimethoxybenzidine)

3D Structure for HMDB0246003 (3,3'-Dimethoxybenzidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra