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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:09:41 UTC

Update Date

2021-09-26 23:05:57 UTC

HMDB ID

HMDB0252995

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Chloro-5-nitro-N-phenylbenzamide

Description

2-chloro-5-nitro-N-phenylbenzamide belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. 2-chloro-5-nitro-N-phenylbenzamide is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-chloro-5-nitro-n-phenylbenzamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Chloro-5-nitro-N-phenylbenzamide 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

HMDB0252995
     RDKit          3D
2-Chloro-5-nitro-N-phenylbenzamide
 28 29  0  0  0  0  0  0  0  0999 V2000
   -0.1297    0.9209   -1.9061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1224    0.1954   -0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627   -0.2573   -0.0608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.0077   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.8449   -1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    1.0290   -1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0141    0.4109   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551   -0.4195    0.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -0.6190    0.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -0.1542   -0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3901    0.6387    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7241    0.3335    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413    1.1810    1.0403 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7277    0.9708    1.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.3149    1.6156 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.2672   -0.7952   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377   -1.5885   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022   -1.2812   -1.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0389   -2.2799   -2.2615 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5330   -0.8681    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416    1.3645   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    1.6888   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0760    0.5927   -0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0803   -0.9228    1.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6401   -1.2768    1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9492    1.5339    0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057   -1.0721   -0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8434   -2.4930   -1.5665 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
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9  4  1  0
 18 10  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 16 27  1  0
 17 28  1  0
M  CHG  2  13   1  15  -1
M  END

GW9
  Mrv0541 02241213422D          

 19 20  0  0  0  0            999 V2000
    1.3288    1.3743    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3288    0.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433   -0.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288   -1.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288   -1.9257    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.0433   -2.3382    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.6144   -2.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144   -0.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1001    0.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1001    1.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8146    0.1368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291    0.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435    0.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9580    0.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9580    1.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435    1.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291    1.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  CHG  2   6   1   7  -1
M  END
> <DATABASE_ID>
HMDB0252995

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H9ClN2O3/c14-12-7-6-10(16(18)19)8-11(12)13(17)15-9-4-2-1-3-5-9/h1-8H,(H,15,17)

> <INCHI_KEY>
DNTSIBUQMRRYIU-UHFFFAOYSA-N

> <FORMULA>
C13H9ClN2O3

> <MOLECULAR_WEIGHT>
276.675

> <EXACT_MASS>
276.030169871

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.13826172175542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-chloro-5-nitro-N-phenylbenzamide

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
3.609159487333333

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.311250106223028

> <JCHEM_PKA_STRONGEST_BASIC>
-4.317107164889544

> <JCHEM_POLAR_SURFACE_AREA>
74.92

> <JCHEM_REFRACTIVITY>
73.72100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-chloro-5-nitrobenzanilide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252995
     RDKit          3D
2-Chloro-5-nitro-N-phenylbenzamide
 28 29  0  0  0  0  0  0  0  0999 V2000
   -0.1297    0.9209   -1.9061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1224    0.1954   -0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627   -0.2573   -0.0608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.0077   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.8449   -1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    1.0290   -1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0141    0.4109   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551   -0.4195    0.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -0.6190    0.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -0.1542   -0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3901    0.6387    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7241    0.3335    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413    1.1810    1.0403 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7277    0.9708    1.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.3149    1.6156 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.2672   -0.7952   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377   -1.5885   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022   -1.2812   -1.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0389   -2.2799   -2.2615 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5330   -0.8681    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416    1.3645   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    1.6888   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0760    0.5927   -0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0803   -0.9228    1.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6401   -1.2768    1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9492    1.5339    0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057   -1.0721   -0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8434   -2.4930   -1.5665 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
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9  4  1  0
 18 10  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 16 27  1  0
 17 28  1  0
M  CHG  2  13   1  15  -1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: GW9                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       2.480   2.565   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0       2.480   1.025   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.814   0.255   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.814  -1.285   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.480  -2.055   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.480  -3.595   0.000  0.00  0.00           N+1
HETATM    7  O   UNK     0       3.814  -4.365   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0       1.147  -4.365   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.147  -1.285   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.147   0.255   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.187   1.025   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.187   2.565   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -1.521   0.255   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -2.854   1.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.188   0.255   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.522   1.025   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.522   2.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.188   3.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.854   2.565   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    2    9   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0252995
HETATM    1  O1  UNL     1      -0.130   0.921  -1.906  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.122   0.195  -0.918  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.863  -0.257  -0.061  1.00  0.00           N  
HETATM    4  C2  UNL     1      -2.239   0.008  -0.150  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.810   0.845  -1.089  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.193   1.029  -1.085  1.00  0.00           C  
HETATM    7  C5  UNL     1      -5.014   0.411  -0.183  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.455  -0.419   0.750  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.103  -0.619   0.770  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.561  -0.154  -0.718  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.390   0.639   0.046  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.724   0.333   0.244  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.541   1.181   1.040  1.00  0.00           N1+
HETATM   14  O2  UNL     1       5.728   0.971   1.256  1.00  0.00           O  
HETATM   15  O3  UNL     1       3.986   2.315   1.616  1.00  0.00           O1-
HETATM   16  C11 UNL     1       4.267  -0.795  -0.332  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.438  -1.589  -1.097  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.102  -1.281  -1.293  1.00  0.00           C  
HETATM   19 CL1  UNL     1       1.039  -2.280  -2.261  1.00  0.00          CL  
HETATM   20  H1  UNL     1      -0.533  -0.868   0.748  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.242   1.364  -1.822  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.620   1.689  -1.829  1.00  0.00           H  
HETATM   23  H4  UNL     1      -6.076   0.593  -0.229  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.080  -0.923   1.478  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.640  -1.277   1.505  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.949   1.534   0.500  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.306  -1.072  -0.204  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.843  -2.493  -1.566  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   20
CONECT    4    5    5    9
CONECT    5    6   21
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   25
CONECT   10   11   11   18
CONECT   11   12   26
CONECT   12   13   16   16
CONECT   13   14   14   15
CONECT   16   17   27
CONECT   17   18   18   28
CONECT   18   19
END

HMDB0252995
     RDKit          3D
2-Chloro-5-nitro-N-phenylbenzamide
 28 29  0  0  0  0  0  0  0  0999 V2000
   -0.1297    0.9209   -1.9061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1224    0.1954   -0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627   -0.2573   -0.0608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389    0.0077   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8103    0.8449   -1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    1.0290   -1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0141    0.4109   -0.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551   -0.4195    0.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -0.6190    0.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -0.1542   -0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3901    0.6387    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7241    0.3335    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413    1.1810    1.0403 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.7277    0.9708    1.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    2.3149    1.6156 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.2672   -0.7952   -0.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377   -1.5885   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022   -1.2812   -1.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0389   -2.2799   -2.2615 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5330   -0.8681    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416    1.3645   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6203    1.6888   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0760    0.5927   -0.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0803   -0.9228    1.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6401   -1.2768    1.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9492    1.5339    0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057   -1.0721   -0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8434   -2.4930   -1.5665 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
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9  4  1  0
 18 10  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 16 27  1  0
 17 28  1  0
M  CHG  2  13   1  15  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Chloro-5-nitrobenzanilide	Kegg
2-Chloro-5-nitro-N-phenylbenzene-1-carboximidate	Generator

Chemical Formula

C₁₃H₉ClN₂O₃

Average Molecular Weight

276.675

Monoisotopic Molecular Weight

276.030169871

IUPAC Name

2-chloro-5-nitro-N-phenylbenzamide

Traditional Name

2-chloro-5-nitrobenzanilide

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C1

InChI Identifier

InChI=1S/C13H9ClN2O3/c14-12-7-6-10(16(18)19)8-11(12)13(17)15-9-4-2-1-3-5-9/h1-8H,(H,15,17)

InChI Key

DNTSIBUQMRRYIU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

Alternative Parents

Substituents

Nitrobenzene
Nitroaromatic compound
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
C-nitro compound
Organic nitro compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboximidic acid
Carboximidic acid derivative
Organic oxoazanium
Organic nitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzamides (CHEBI:79993 )

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	3.39	ALOGPS
logP	3.61	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.72 m³·mol⁻¹	ChemAxon
Polarizability	26.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	156.782	30932474
DeepCCS	[M-H]-	154.386	30932474
DeepCCS	[M-2H]-	188.064	30932474
DeepCCS	[M+Na]+	163.132	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.6	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.7	32859911
AllCCS	[M-H]-	156.2	32859911
AllCCS	[M+Na-2H]-	155.5	32859911
AllCCS	[M+HCOO]-	154.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.1415 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2241.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	464.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	273.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	170.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	575.2 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	699.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1337.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	495.5 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	1398.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	496.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	447.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	328.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	54.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Chloro-5-nitro-N-phenylbenzamide	[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C1	3709.3	Standard polar	33892256
2-Chloro-5-nitro-N-phenylbenzamide	[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C1	2441.9	Standard non polar	33892256
2-Chloro-5-nitro-N-phenylbenzamide	[O-][N+](=O)C1=CC=C(Cl)C(=C1)C(=O)NC1=CC=CC=C1	2470.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Chloro-5-nitro-N-phenylbenzamide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C1	2306.8	Semi standard non polar	33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C1	2339.2	Standard non polar	33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C1	3069.4	Standard polar	33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C1	2579.4	Semi standard non polar	33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C1	2527.9	Standard non polar	33892256
2-Chloro-5-nitro-N-phenylbenzamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC([N+](=O)[O-])=CC=C1Cl)C1=CC=CC=C1	3122.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-9340000000-dcec9154f7dde8c70a03	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 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 - 2-Chloro-5-nitro-N-phenylbenzamide LC-ESI-qTof , Positive-QTOF	splash10-00dj-3960000000-a7dc9d06200fd3114dc2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide , positive-QTOF	splash10-0a4i-3930000000-98176efec89b70f91a6c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 15V, Negative-QTOF	splash10-0a4i-0910000000-8be5c84ea794d6ed15a0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 30V, Negative-QTOF	splash10-0a4i-0900000000-7dfd29352a5856b03c62	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 60V, Negative-QTOF	splash10-0a4i-1900000000-e6cce40ef76ff4d6ab01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 45V, Negative-QTOF	splash10-0a4i-0900000000-57ae4308b3ba8e03107e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 10V, Positive-QTOF	splash10-004i-0090000000-5028a8df8f9b81c93917	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 20V, Positive-QTOF	splash10-004i-0090000000-60da5ea2b61310aaf700	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 40V, Positive-QTOF	splash10-004i-3790000000-23e99fa001a60441a626	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 10V, Negative-QTOF	splash10-004i-0090000000-39fedeb9a2a6430d9b90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 20V, Negative-QTOF	splash10-004i-0090000000-dffc08dc66c339eafabd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-nitro-N-phenylbenzamide 40V, Negative-QTOF	splash10-004l-5290000000-6304f208af68870bab32	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

DB07863

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15627

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

644213

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 2-Chloro-5-nitro-N-phenylbenzamide (HMDB0252995)

MOL for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

3D MOL for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

3D SDF for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

3D-SDF for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

PDB for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

3D PDB for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

SMILES for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

INCHI for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

Structure for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

3D Structure for HMDB0252995 (2-Chloro-5-nitro-N-phenylbenzamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra