Showing metabocard for nitrobenzene (MMDBc0054608)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:20:58 UTC
Update Date2024-09-27 18:18:41 UTC
Metabolite IDMMDBc0054608
Metabolite Identification
Common Namenitrobenzene
DescriptionApproximately 95% of nitrobenzene is consumed in the production of aniline, which is a precursor to rubber chemicals, pesticides, dyes, explosives, and pharmaceuticals. Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents. Nitrobenzene is prepared by nitration of benzene with a mixture of concentrated sulfuric acid, water, and nitric acid. This mixture is sometimes called 'mixed acid.' The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction ( delta H = 117 kJ/mol).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f46e4b1d578>


  Mrv1652303202019002D          

  9  9  0  0  0  0            999 V2000
    0.7145   -0.4125    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    0.0000    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
    0.0000    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    2.0625    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f46e4b1d578>

HMDB0041950
     RDKit          3D
Nitrobenzene
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.9444   -1.0508   -0.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -0.0577   -0.0918 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.0550    1.0532    0.2649 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8818   -0.0218   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282   -1.1185   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -1.1056   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    0.0236    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792    1.1166    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2084    1.1075    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6393   -2.0180   -0.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8549   -1.9777   -0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    0.0681    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029    2.0063    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069    1.9748    0.6505 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
  8  9  2  0
  9  4  1  0
  5 10  1  0
  6 11  1  0
  7 12  1  0
  8 13  1  0
  9 14  1  0
M  CHG  2   2   1   3  -1
M  END
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3D SDF for #<Metabolite:0x00007f46e4b1d578>


  Mrv1652303202019002D          

  9  9  0  0  0  0            999 V2000
    0.7145   -0.4125    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    0.0000    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
    0.0000    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    2.0625    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054608

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H

> <INCHI_KEY>
LQNUZADURLCDLV-UHFFFAOYSA-N

> <FORMULA>
C6H5NO2

> <MOLECULAR_WEIGHT>
123.1094

> <EXACT_MASS>
123.032028409

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
11.263492274669511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
nitrobenzene

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.9132300053333333

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.634151969747997

> <JCHEM_POLAR_SURFACE_AREA>
43.14

> <JCHEM_REFRACTIVITY>
32.3785

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitrobenzene

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f46e4b1d578>

HMDB0041950
     RDKit          3D
Nitrobenzene
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.9444   -1.0508   -0.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -0.0577   -0.0918 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.0550    1.0532    0.2649 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.8818   -0.0218   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282   -1.1185   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2646   -1.1056   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    0.0236    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792    1.1166    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2084    1.1075    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6393   -2.0180   -0.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8549   -1.9777   -0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    0.0681    0.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029    2.0063    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069    1.9748    0.6505 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
  8  9  2  0
  9  4  1  0
  5 10  1  0
  6 11  1  0
  7 12  1  0
  8 13  1  0
  9 14  1  0
M  CHG  2   2   1   3  -1
M  END
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PDB for #<Metabolite:0x00007f46e4b1d578>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   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   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x00007f46e4b1d578>

COMPND    HMDB0041950
HETATM    1  O1  UNL     1       2.944  -1.051  -0.452  1.00  0.00           O  
HETATM    2  N1  UNL     1       2.305  -0.058  -0.092  1.00  0.00           N1+
HETATM    3  O2  UNL     1       3.055   1.053   0.265  1.00  0.00           O1-
HETATM    4  C1  UNL     1       0.882  -0.022  -0.035  1.00  0.00           C  
HETATM    5  C2  UNL     1       0.128  -1.119  -0.387  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.265  -1.106  -0.339  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.943   0.024   0.069  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.179   1.117   0.419  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.208   1.108   0.372  1.00  0.00           C  
HETATM   10  H1  UNL     1       0.639  -2.018  -0.711  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.855  -1.978  -0.619  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.024   0.068   0.118  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.703   2.006   0.740  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.807   1.975   0.651  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5    9
CONECT    5    6   10
CONECT    6    7    7   11
CONECT    7    8   12
CONECT    8    9    9   13
CONECT    9   14
END
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SMILES for #<Metabolite:0x00007f46e4b1d578>

O=N(=O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f46e4b1d578>

InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H
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Synonyms
ValueSource
NitrobenzolChEBI
Oil OF mirbaneChEBI
4-HydroxynitrobenzeneHMDB
4-NitrophenolHMDB
Essence OF mirbaneHMDB
Essence OF myrbaneHMDB
Hydroxy(phenyl)azane oxide (acd/name 4.0)HMDB
Mirbane oilHMDB
NiphenHMDB
Nitro-benzeneHMDB
NitrobenzeenHMDB
NitrobenzenHMDB
Nitrobenzol, liquid(dot)HMDB
Oil OF myrbaneHMDB
p-NitrophenolHMDB
PNPHMDB
PNP, p-NitrophenolHMDB
Rcra waste number u169HMDB
Molecular FormulaC6H5NO2
Average Mass123.1094
Monoisotopic Mass123.032028409
IUPAC Namenitrobenzene
Traditional Namenitrobenzene
CAS Registry NumberNot Available
SMILES
O=N(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H
InChI KeyLQNUZADURLCDLV-UHFFFAOYSA-N