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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:21:12 UTC

Update Date

2021-09-26 22:56:59 UTC

HMDB ID

HMDB0247345

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N,N'-Diphenyl-p-phenylenediamine

Description

N,N'-Diphenyl-p-phenylenediamine, also known as 4-phenylaminodiphenylamine or DPPD, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Based on a literature review a significant number of articles have been published on N,N'-Diphenyl-p-phenylenediamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N,n'-diphenyl-p-phenylenediamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N,N'-Diphenyl-p-phenylenediamine 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

HMDB0247345
     RDKit          3D
N,N'-Diphenyl-p-phenylenediamine
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1487    0.6255    0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472    1.4143    0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542    0.9651    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620   -0.2269   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.6979   -0.9095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -0.3297   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -0.3060   -1.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740    0.0203   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    0.3448    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438    0.6610    1.1683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.1779    0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -0.9777   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878   -1.3700   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2100   -0.6006   -0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595    0.5549    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.9521    0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    0.3210    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0954   -0.0055    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9124   -1.0105   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0839   -0.5756    0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0966    0.9557    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    2.3510    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732    1.6026    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -1.3372   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -0.5607   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269    0.0474   -1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753    1.2653    2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -1.6183   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1436   -2.2805   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889   -0.8618   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327    1.2040    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8307    1.8873    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955    0.5790    2.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416   -0.0281    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8796   -1.9699   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9999   -1.1725    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20  1  1  0
 18  6  1  0
 16 11  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv1572004191604142D          

 20 22  0  0  0  0            999 V2000
   -0.7145    3.7125    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
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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
   -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
    0.0000    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
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  2  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247345

> <DATABASE_NAME>
hmdb

> <SMILES>
N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16N2/c1-3-7-15(8-4-1)19-17-11-13-18(14-12-17)20-16-9-5-2-6-10-16/h1-14,19-20H

> <INCHI_KEY>
UTGQNNCQYDRXCH-UHFFFAOYSA-N

> <FORMULA>
C18H16N2

> <MOLECULAR_WEIGHT>
260.34

> <EXACT_MASS>
260.131348523

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.917395830845738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N1,N4-diphenylbenzene-1,4-diamine

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
4.853097366666667

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.4169088691898417

> <JCHEM_POLAR_SURFACE_AREA>
24.06

> <JCHEM_REFRACTIVITY>
83.03040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DFFD

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0247345
     RDKit          3D
N,N'-Diphenyl-p-phenylenediamine
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1487    0.6255    0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472    1.4143    0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542    0.9651    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620   -0.2269   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.6979   -0.9095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -0.3297   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -0.3060   -1.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740    0.0203   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    0.3448    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438    0.6610    1.1683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.1779    0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -0.9777   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878   -1.3700   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2100   -0.6006   -0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595    0.5549    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.9521    0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    0.3210    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0954   -0.0055    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9124   -1.0105   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0839   -0.5756    0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0966    0.9557    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    2.3510    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732    1.6026    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -1.3372   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -0.5607   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269    0.0474   -1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753    1.2653    2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -1.6183   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1436   -2.2805   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889   -0.8618   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327    1.2040    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8307    1.8873    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955    0.5790    2.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416   -0.0281    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8796   -1.9699   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9999   -1.1725    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20  1  1  0
 18  6  1  0
 16 11  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  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      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   15                                                       
CONECT    8    4   15                                                       
CONECT    9    5   16                                                       
CONECT   10    6   16                                                       
CONECT   11   13   17                                                       
CONECT   12   14   17                                                       
CONECT   13   11   18                                                       
CONECT   14   12   18                                                       
CONECT   15    7    8   19                                                  
CONECT   16    9   10   20                                                  
CONECT   17   11   12   19                                                  
CONECT   18   13   14   20                                                  
CONECT   19   15   17                                                       
CONECT   20   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0247345
HETATM    1  C1  UNL     1       6.149   0.626   0.791  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.047   1.414   0.911  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.854   0.965   0.329  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.762  -0.227  -0.347  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.558  -0.698  -0.910  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.304  -0.330  -0.395  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.164  -0.306  -1.206  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.074   0.020  -0.713  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.280   0.345   0.611  1.00  0.00           C  
HETATM   10  N2  UNL     1      -2.544   0.661   1.168  1.00  0.00           N  
HETATM   11  C9  UNL     1      -3.734   0.178   0.611  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.864  -0.978  -0.119  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.088  -1.370  -0.666  1.00  0.00           C  
HETATM   14  C12 UNL     1      -6.210  -0.601  -0.486  1.00  0.00           C  
HETATM   15  C13 UNL     1      -6.060   0.555   0.250  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.868   0.952   0.792  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.138   0.321   1.424  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.095  -0.005   0.925  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.912  -1.011  -0.451  1.00  0.00           C  
HETATM   20  C18 UNL     1       6.084  -0.576   0.116  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.097   0.956   1.238  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.024   2.351   1.416  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.973   1.603   0.402  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.599  -1.337  -1.730  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.316  -0.561  -2.249  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.927   0.047  -1.384  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.575   1.265   2.011  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.007  -1.618  -0.263  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.144  -2.280  -1.230  1.00  0.00           H  
HETATM   30  H10 UNL     1      -7.189  -0.862  -0.891  1.00  0.00           H  
HETATM   31  H11 UNL     1      -6.933   1.204   0.422  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.831   1.887   1.366  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.295   0.579   2.478  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.942  -0.028   1.614  1.00  0.00           H  
HETATM   35  H15 UNL     1       4.880  -1.970  -0.985  1.00  0.00           H  
HETATM   36  H16 UNL     1       7.000  -1.172   0.048  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4    4   23
CONECT    4    5   19
CONECT    5    6   24
CONECT    6    7    7   18
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   17
CONECT   10   11   27
CONECT   11   12   12   16
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   32
CONECT   17   18   18   33
CONECT   18   34
CONECT   19   20   20   35
CONECT   20   36
END

HMDB0247345
     RDKit          3D
N,N'-Diphenyl-p-phenylenediamine
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1487    0.6255    0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472    1.4143    0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542    0.9651    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620   -0.2269   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.6979   -0.9095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -0.3297   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -0.3060   -1.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740    0.0203   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    0.3448    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438    0.6610    1.1683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.1779    0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -0.9777   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878   -1.3700   -0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2100   -0.6006   -0.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595    0.5549    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.9521    0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    0.3210    1.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0954   -0.0055    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9124   -1.0105   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0839   -0.5756    0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0966    0.9557    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    2.3510    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732    1.6026    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -1.3372   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -0.5607   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269    0.0474   -1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753    1.2653    2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -1.6183   -0.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1436   -2.2805   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889   -0.8618   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327    1.2040    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8307    1.8873    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955    0.5790    2.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416   -0.0281    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8796   -1.9699   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9999   -1.1725    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20  1  1  0
 18  6  1  0
 16 11  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Bis(phenylamino)benzene	ChEBI
1,4-Dianilinobenzene	ChEBI
4,4'-Diphenyl-p-phenylenediamine	ChEBI
4-Phenylaminodiphenylamine	ChEBI
Diphenyl-p-phenylenediamine	ChEBI
DPPD	ChEBI
N,N'-diphenyl-1,4-benzenediamine	ChEBI
N,N'-diphenyl-1,4-diaminobenzene	ChEBI
p-Bis(phenylamino)benzene	ChEBI
p-Phenylaminodiphenylamine	ChEBI
N,N'-diphenyl-4-phenylenediamine	HMDB
DDPD	HMDB
N,N'-diphenyl-1,4-phenylenediamine	HMDB
N,N'-diphenyl-P-phenylenediamine	ChEBI

Chemical Formula

C₁₈H₁₆N₂

Average Molecular Weight

260.34

Monoisotopic Molecular Weight

260.131348523

IUPAC Name

N1,N4-diphenylbenzene-1,4-diamine

Traditional Name

DFFD

CAS Registry Number

Not Available

SMILES

N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C18H16N2/c1-3-7-15(8-4-1)19-17-11-13-18(14-12-17)20-16-9-5-2-6-10-16/h1-14,19-20H

InChI Key

UTGQNNCQYDRXCH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

Aniline or substituted anilines
Secondary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:34860 )
N-substituted diamine (CHEBI:34860 )

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	4.73	ALOGPS
logP	4.85	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	2.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	24.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.03 m³·mol⁻¹	ChemAxon
Polarizability	29.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.178	30932474
DeepCCS	[M-H]-	159.82	30932474
DeepCCS	[M-2H]-	192.707	30932474
DeepCCS	[M+Na]+	168.272	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	166.9	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	16.6796 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2665.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	502.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	248.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	834.3 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	830.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1496.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	423.2 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	1269.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	468.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	492.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	97.9 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	11.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N,N'-Diphenyl-p-phenylenediamine	N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	3419.0	Standard polar	33892256
N,N'-Diphenyl-p-phenylenediamine	N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	2619.8	Standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine	N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	2769.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N,N'-Diphenyl-p-phenylenediamine,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	2773.9	Semi standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	2500.1	Standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	3293.4	Standard polar	33892256
N,N'-Diphenyl-p-phenylenediamine,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	2605.7	Semi standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	2534.8	Standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C)C=C1	2928.6	Standard polar	33892256
N,N'-Diphenyl-p-phenylenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	2952.6	Semi standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	2675.3	Standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(NC2=CC=CC=C2)C=C1	3353.9	Standard polar	33892256
N,N'-Diphenyl-p-phenylenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	2981.2	Semi standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	2903.3	Standard non polar	33892256
N,N'-Diphenyl-p-phenylenediamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=C(N(C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	3083.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N,N'-Diphenyl-p-phenylenediamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-2390000000-d040411419e49602e250	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 10V, Positive-QTOF	splash10-03di-0090000000-bd251d1ae78c2ff88fa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 20V, Positive-QTOF	splash10-03xr-1690000000-395ce6b56786da70acad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 40V, Positive-QTOF	splash10-014i-2900000000-8f51dc6b175967c58d2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 10V, Negative-QTOF	splash10-0a4i-0090000000-bf39d4fa3a78097d8477	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 20V, Negative-QTOF	splash10-0a4i-1090000000-944bf0b1fb52166aa039	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 40V, Negative-QTOF	splash10-0006-9330000000-9418ac04018b69f8378d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 10V, Positive-QTOF	splash10-03di-0090000000-2f16209866e7f29988de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 20V, Positive-QTOF	splash10-03di-0090000000-844d63f94b0211ee9606	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 40V, Positive-QTOF	splash10-0a7i-3980000000-20eed10e05bcb5308aad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 10V, Negative-QTOF	splash10-0a4i-0090000000-cd7631b883f8a7ce97fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 20V, Negative-QTOF	splash10-0a4i-0090000000-3b214a7f65745556d48f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N,N'-Diphenyl-p-phenylenediamine 40V, Negative-QTOF	splash10-0a4i-1390000000-c71accb47a6c4106efba	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

6080

KEGG Compound ID

C14501

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6319

PDB ID

Not Available

ChEBI ID

34860

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1262451

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 N,N'-Diphenyl-p-phenylenediamine (HMDB0247345)

MOL for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

3D MOL for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

3D SDF for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

3D-SDF for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

PDB for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

3D PDB for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

SMILES for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

INCHI for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

Structure for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

3D Structure for HMDB0247345 (N,N'-Diphenyl-p-phenylenediamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra