Showing metabocard for 1-chloro-2,4-dinitrobenzene (MMDBc0054115)

Pharmaceutical
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 22:53:54 UTC
Update Date2025-10-07 16:04:11 UTC
Metabolite IDMMDBc0054115
Metabolite Identification
Common Name1-chloro-2,4-dinitrobenzene
Description1-chloro-2,4-dinitrobenzene is a synthetic organic compound belonging to the class of nitroaromatic compounds. Its chemical structure features a benzene ring substituted with one chlorine atom and two nitro groups at the 2 and 4 positions, which contributes to its reactivity and potential as a metabolic substrate. In biological contexts, 1-chloro-2,4-dinitrobenzene (DNCB) has been employed in experimental models, such as BALB/c mice, to assess inflammatory responses (PMID:41029337 ). Additionally, it serves as a substrate in enzyme kinetics studies, particularly in evaluating the activity of glutathione S-transferases, where it has been shown that CaGSTU1-1 exhibits superior hydroperoxidase activity and thermal stability when interacting with model substrates, including cumene hydroperoxide and 1-chloro-2,4-dinitrobenzene (PMID:41022292 ). This compound's reactivity and role in enzymatic pathways underscore its significance in biochemical research and toxicology.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9ab708de10>

Structure #1
  Mrv0541 02241206292D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
  9 13  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9ab708de10>

HMDB0243844
     RDKit          3D
1-Chloro-2,4-dinitrobenzene
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1508   -2.4946   -0.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3093   -1.3160   -0.0545 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5661   -0.8599    0.2422 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1849   -0.4579    0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435    0.8785    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533    1.7188    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9867    1.2051    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3524    2.3024    0.3100 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -0.1101   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799   -0.5592   -0.4978 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.7218   -1.4786   -1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5420    0.0668    0.1120 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.0692   -0.9363   -0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.2546    0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722    2.7705    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926   -1.9839   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13  4  1  0
  5 14  1  0
  6 15  1  0
 13 16  1  0
M  CHG  4   2   1   3  -1  10   1  12  -1
M  END
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3D SDF for #<Metabolite:0x00007f9ab708de10>

Structure #1
  Mrv0541 02241206292D          

 13 13  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
  9 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054115

> <DATABASE_NAME>
MIME

> <SMILES>
ClC1=C(C=C(C=C1)N(=O)=O)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

> <INCHI_KEY>
VYZAHLCBVHPDDF-UHFFFAOYSA-N

> <FORMULA>
C6H3ClN2O4

> <MOLECULAR_WEIGHT>
202.552

> <EXACT_MASS>
201.978134301

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.726781813685436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-chloro-2,4-dinitrobenzene

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.457258871

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.936760959463875

> <JCHEM_POLAR_SURFACE_AREA>
91.63999999999999

> <JCHEM_REFRACTIVITY>
45.5122

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Cdnb

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f9ab708de10>

HMDB0243844
     RDKit          3D
1-Chloro-2,4-dinitrobenzene
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1508   -2.4946   -0.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3093   -1.3160   -0.0545 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5661   -0.8599    0.2422 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1849   -0.4579    0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435    0.8785    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533    1.7188    0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9867    1.2051    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3524    2.3024    0.3100 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -0.1101   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799   -0.5592   -0.4978 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.7218   -1.4786   -1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5420    0.0668    0.1120 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.0692   -0.9363   -0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.2546    0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722    2.7705    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926   -1.9839   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13  4  1  0
  5 14  1  0
  6 15  1  0
 13 16  1  0
M  CHG  4   2   1   3  -1  10   1  12  -1
M  END
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PDB for #<Metabolite:0x00007f9ab708de10>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   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  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM    8  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    8                                                  
CONECT    5    2    6    7                                                  
CONECT    6    3    5    9                                                  
CONECT    7    5                                                            
CONECT    8    4   10   11                                                  
CONECT    9    6   12   13                                                  
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007f9ab708de10>

COMPND    HMDB0243844
HETATM    1  O1  UNL     1      -2.151  -2.495  -0.401  1.00  0.00           O  
HETATM    2  N1  UNL     1      -2.309  -1.316  -0.055  1.00  0.00           N1+
HETATM    3  O2  UNL     1      -3.566  -0.860   0.242  1.00  0.00           O1-
HETATM    4  C1  UNL     1      -1.185  -0.458   0.029  1.00  0.00           C  
HETATM    5  C2  UNL     1      -1.343   0.879   0.420  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.253   1.719   0.503  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.987   1.205   0.193  1.00  0.00           C  
HETATM    8 CL1  UNL     1       2.352   2.302   0.310  1.00  0.00          CL  
HETATM    9  C5  UNL     1       1.168  -0.110  -0.195  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.480  -0.559  -0.498  1.00  0.00           N1+
HETATM   11  O3  UNL     1       2.722  -1.479  -1.277  1.00  0.00           O  
HETATM   12  O4  UNL     1       3.542   0.067   0.112  1.00  0.00           O1-
HETATM   13  C6  UNL     1       0.069  -0.936  -0.273  1.00  0.00           C  
HETATM   14  H1  UNL     1      -2.333   1.255   0.658  1.00  0.00           H  
HETATM   15  H2  UNL     1      -0.372   2.770   0.810  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.193  -1.984  -0.580  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5   13
CONECT    5    6   14
CONECT    6    7    7   15
CONECT    7    8    9
CONECT    9   10   13   13
CONECT   10   11   11   12
CONECT   13   16
END
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SMILES for #<Metabolite:0x00007f9ab708de10>

ClC1=C(C=C(C=C1)N(=O)=O)N(=O)=O
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INCHI for #<Metabolite:0x00007f9ab708de10>

InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
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Synonyms
ValueSource
1,3-Dinitro-4-chlorobenzeneChEBI
1-Chloro-2,4-dinitrobenzolChEBI
2,4-Dinitro-1-chlorobenzeneChEBI
2,4-DinitrochlorobenzeneChEBI
2,4-Dinitrophenyl chlorideChEBI
4-Chloro-1,3-dinitrobenzeneChEBI
6-Chloro-1,3-dinitrobenzeneChEBI
CDNBChEBI
ChlorodinitrobenzeneChEBI
CLDNBChEBI
DinitrochlorobenzeneChEBI
DNCBChEBI
DNPCLChEBI
1 Chloro 2,4 dinitrobenzeneHMDB
1-Chloro-2,4-dinitrobenzeneKEGG
Molecular FormulaC6H3ClN2O4
Average Mass202.552
Monoisotopic Mass201.978134301
IUPAC Name1-chloro-2,4-dinitrobenzene
Traditional NameCdnb
CAS Registry NumberNot Available
SMILES
ClC1=C(C=C(C=C1)N(=O)=O)N(=O)=O
InChI Identifier
InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
InChI KeyVYZAHLCBVHPDDF-UHFFFAOYSA-N