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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:20:32 UTC

Update Date

2021-09-26 22:51:43 UTC

HMDB ID

HMDB0244158

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,3-Bis(4-nitrophenyl)urea

Description

1,3-Bis(4-nitrophenyl)urea, also known as 4,4-DNC or 4,4'-dinitrocarbanilide, belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group. Based on a literature review a small amount of articles have been published on 1,3-Bis(4-nitrophenyl)urea. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,3-bis(4-nitrophenyl)urea is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,3-Bis(4-nitrophenyl)urea 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

HMDB0244158
     RDKit          3D
1,3-Bis(4-nitrophenyl)urea
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.0837   -0.1685    0.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    0.0514   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.3759   -1.0153 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697    0.5005   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    0.9558   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7573    1.0846   -1.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    0.7671    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5340    0.8968    0.5402 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.8542    0.5992    1.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4690    1.3409   -0.3481 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.2155    0.3211    1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608    0.1823    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -0.0200   -0.8768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5092   -0.3230   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564   -0.3461   -1.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952   -0.6318   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1078   -0.9185    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4120   -1.2141    1.2011 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.5868   -1.4697    2.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4688   -1.2166    0.3552 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0027   -0.9032    1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405   -0.6113    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    0.5497   -2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306    1.2110   -2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5234    1.4382   -1.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227    0.0679    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -0.1794    1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633    0.1782   -1.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -0.1264   -2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7893   -0.6478   -1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567   -1.1264    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176   -0.6177    1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 12  4  1  0
 22 14  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 21 31  1  0
 22 32  1  0
M  CHG  4   8   1  10  -1  18   1  20  -1
M  END


  Mrv1572004221604182D          

 22 23  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    3.7125    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    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    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    3.3000    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    4.9500    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    2.0625    0.0000 C   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
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    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
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 16  2  0  0  0  0
 20 16  2  0  0  0  0
 21 17  2  0  0  0  0
 22 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244158

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H10N4O5/c18-13(14-9-1-5-11(6-2-9)16(19)20)15-10-3-7-12(8-4-10)17(21)22/h1-8H,(H2,14,15,18)

> <INCHI_KEY>
JEZZOKXIXNSKQD-UHFFFAOYSA-N

> <FORMULA>
C13H10N4O5

> <MOLECULAR_WEIGHT>
302.246

> <EXACT_MASS>
302.065119438

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.241230057716525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(4-nitrophenyl)urea

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.998623539666666

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.270482810254169

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.991420207864083

> <JCHEM_PKA_STRONGEST_BASIC>
-4.945174413033081

> <JCHEM_POLAR_SURFACE_AREA>
132.76999999999998

> <JCHEM_REFRACTIVITY>
80.70219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
urea, N,N'-bis(4-nitrophenyl)-

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244158
     RDKit          3D
1,3-Bis(4-nitrophenyl)urea
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.0837   -0.1685    0.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    0.0514   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.3759   -1.0153 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697    0.5005   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    0.9558   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7573    1.0846   -1.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    0.7671    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5340    0.8968    0.5402 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.8542    0.5992    1.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4690    1.3409   -0.3481 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.2155    0.3211    1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608    0.1823    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -0.0200   -0.8768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5092   -0.3230   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564   -0.3461   -1.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952   -0.6318   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1078   -0.9185    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4120   -1.2141    1.2011 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.5868   -1.4697    2.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4688   -1.2166    0.3552 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0027   -0.9032    1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405   -0.6113    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    0.5497   -2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306    1.2110   -2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5234    1.4382   -1.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227    0.0679    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -0.1794    1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633    0.1782   -1.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -0.1264   -2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7893   -0.6478   -1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567   -1.1264    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176   -0.6177    1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 12  4  1  0
 22 14  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 21 31  1  0
 22 32  1  0
M  CHG  4   8   1  10  -1  18   1  20  -1
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-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   6.930   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -2.667   4.620   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -2.667  10.780   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001  11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
CONECT    1    5    9                                                       
CONECT    2    6    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    1    2   14                                                  
CONECT   10    3    4   15                                                  
CONECT   11    5    6   16                                                  
CONECT   12    7    8   17                                                  
CONECT   13   14   15   18                                                  
CONECT   14    9   13                                                       
CONECT   15   10   13                                                       
CONECT   16   11   19   20                                                  
CONECT   17   12   21   22                                                  
CONECT   18   13                                                            
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0244158
HETATM    1  O1  UNL     1       0.084  -0.169   0.989  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.002   0.051  -0.234  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.133   0.376  -1.015  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.470   0.501  -0.597  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.442   0.956  -1.500  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.757   1.085  -1.134  1.00  0.00           C  
HETATM    7  C5  UNL     1       5.173   0.767   0.149  1.00  0.00           C  
HETATM    8  N2  UNL     1       6.534   0.897   0.540  1.00  0.00           N1+
HETATM    9  O2  UNL     1       6.854   0.599   1.701  1.00  0.00           O  
HETATM   10  O3  UNL     1       7.469   1.341  -0.348  1.00  0.00           O1-
HETATM   11  C6  UNL     1       4.215   0.321   1.030  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.861   0.182   0.673  1.00  0.00           C  
HETATM   13  N3  UNL     1      -1.255  -0.020  -0.877  1.00  0.00           N  
HETATM   14  C8  UNL     1      -2.509  -0.323  -0.305  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.656  -0.346  -1.117  1.00  0.00           C  
HETATM   16  C10 UNL     1      -4.895  -0.632  -0.624  1.00  0.00           C  
HETATM   17  C11 UNL     1      -5.108  -0.918   0.709  1.00  0.00           C  
HETATM   18  N4  UNL     1      -6.412  -1.214   1.201  1.00  0.00           N1+
HETATM   19  O4  UNL     1      -6.587  -1.470   2.401  1.00  0.00           O  
HETATM   20  O5  UNL     1      -7.469  -1.217   0.355  1.00  0.00           O1-
HETATM   21  C12 UNL     1      -4.003  -0.903   1.527  1.00  0.00           C  
HETATM   22  C13 UNL     1      -2.741  -0.611   1.020  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.952   0.550  -2.071  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.131   1.211  -2.516  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.523   1.438  -1.828  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.523   0.068   2.039  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.189  -0.179   1.434  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.263   0.178  -1.924  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.547  -0.126  -2.181  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.789  -0.648  -1.266  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.157  -1.126   2.574  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.918  -0.618   1.723  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4   23
CONECT    4    5    5   12
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   11   12   12   26
CONECT   12   27
CONECT   13   14   28
CONECT   14   15   15   22
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   18   21
CONECT   18   19   19   20
CONECT   21   22   22   31
CONECT   22   32
END

HMDB0244158
     RDKit          3D
1,3-Bis(4-nitrophenyl)urea
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.0837   -0.1685    0.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    0.0514   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.3759   -1.0153 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697    0.5005   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    0.9558   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7573    1.0846   -1.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    0.7671    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5340    0.8968    0.5402 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.8542    0.5992    1.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4690    1.3409   -0.3481 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.2155    0.3211    1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608    0.1823    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -0.0200   -0.8768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5092   -0.3230   -0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6564   -0.3461   -1.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952   -0.6318   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1078   -0.9185    0.7089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4120   -1.2141    1.2011 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.5868   -1.4697    2.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4688   -1.2166    0.3552 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0027   -0.9032    1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405   -0.6113    1.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    0.5497   -2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1306    1.2110   -2.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5234    1.4382   -1.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5227    0.0679    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -0.1794    1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633    0.1782   -1.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470   -0.1264   -2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7893   -0.6478   -1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567   -1.1264    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9176   -0.6177    1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 12  4  1  0
 22 14  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 21 31  1  0
 22 32  1  0
M  CHG  4   8   1  10  -1  18   1  20  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N,N'-bis(4-nitrophenyl)urea	HMDB
4,4-DNC	HMDB
4,4'-Dinitrocarbanilide	HMDB

Chemical Formula

C₁₃H₁₀N₄O₅

Average Molecular Weight

302.246

Monoisotopic Molecular Weight

302.065119438

IUPAC Name

1,3-bis(4-nitrophenyl)urea

Traditional Name

urea, N,N'-bis(4-nitrophenyl)-

CAS Registry Number

Not Available

SMILES

O=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O

InChI Identifier

InChI=1S/C13H10N4O5/c18-13(14-9-1-5-11(6-2-9)16(19)20)15-10-3-7-12(8-4-10)17(21)22/h1-8H,(H2,14,15,18)

InChI Key

JEZZOKXIXNSKQD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-phenylureas. N-phenylureas are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

N-phenylureas

Direct Parent

N-phenylureas

Alternative Parents

Substituents

N-phenylurea
Nitrobenzene
Nitroaromatic compound
C-nitro compound
Carbonic acid derivative
Urea
Organic nitro compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.48	ALOGPS
logP	3	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.99	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	132.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.7 m³·mol⁻¹	ChemAxon
Polarizability	28.24 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]+	170.526	30932474
DeepCCS	[M-H]-	168.168	30932474
DeepCCS	[M-2H]-	201.123	30932474
DeepCCS	[M+Na]+	176.619	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	161.9	32859911
AllCCS	[M+NH4]+	168.4	32859911
AllCCS	[M+Na]+	169.2	32859911
AllCCS	[M-H]-	166.4	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	164.4	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.	5.01 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6975 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1445.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	414.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	99.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	221.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	399.3 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	566.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1103.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	366.2 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	1150.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	511.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	506.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	464.4 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	267.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,3-Bis(4-nitrophenyl)urea	O=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O	4183.9	Standard polar	33892256
1,3-Bis(4-nitrophenyl)urea	O=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O	3111.8	Standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea	O=C(NC1=CC=C(C=C1)N(=O)=O)NC1=CC=C(C=C1)N(=O)=O	3380.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,3-Bis(4-nitrophenyl)urea,1TMS,isomer #1	C[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C1	3125.9	Semi standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,1TMS,isomer #1	C[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C1	2881.6	Standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,1TMS,isomer #1	C[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C1	4003.0	Standard polar	33892256
1,3-Bis(4-nitrophenyl)urea,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	2866.8	Semi standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	2824.0	Standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	3547.9	Standard polar	33892256
1,3-Bis(4-nitrophenyl)urea,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C1	3497.8	Semi standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C1	3064.1	Standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)C1=CC=C([N+](=O)[O-])C=C1	3949.3	Standard polar	33892256
1,3-Bis(4-nitrophenyl)urea,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	3544.5	Semi standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	3216.8	Standard non polar	33892256
1,3-Bis(4-nitrophenyl)urea,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)C1=CC=C([N+](=O)[O-])C=C1	3563.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Bis(4-nitrophenyl)urea GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5901000000-7a78a0dfb08ca55ec2db	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 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 - 1,3-Bis(4-nitrophenyl)urea 10V, Positive-QTOF	splash10-0udi-0009000000-67304ebc09ba8b940ddc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 20V, Positive-QTOF	splash10-0udr-0059000000-43ba693b3478b975dede	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 40V, Positive-QTOF	splash10-0uds-1935000000-1595a3eaa8c6b573a55e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 10V, Negative-QTOF	splash10-0udi-0009000000-30aaab4c306a79c55ff7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 20V, Negative-QTOF	splash10-0udi-0009000000-22a5325e86b9b55d7226	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,3-Bis(4-nitrophenyl)urea 40V, Negative-QTOF	splash10-0f6y-3902000000-5d06ba13a1db025e754d	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9137

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9509

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 1,3-Bis(4-nitrophenyl)urea (HMDB0244158)

MOL for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

3D MOL for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

3D SDF for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

3D-SDF for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

PDB for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

3D PDB for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

SMILES for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

INCHI for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

Structure for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

3D Structure for HMDB0244158 (1,3-Bis(4-nitrophenyl)urea)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra