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Showing metabocard for Nitrobenzene (HMDB0041950)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:34 UTC
Update Date2023-02-21 17:29:04 UTC
HMDB IDHMDB0041950
Secondary Accession Numbers
  • HMDB41950
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
Data?1677000544
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041950 (Nitrobenzene)

  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 HMDB0041950 (Nitrobenzene)

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 HMDB0041950 (Nitrobenzene)

  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>
HMDB0041950

> <DATABASE_NAME>
hmdb

> <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 HMDB0041950 (Nitrobenzene)

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 HMDB0041950 (Nitrobenzene)

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 HMDB0041950 (Nitrobenzene)

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 HMDB0041950 (Nitrobenzene)

O=N(=O)C1=CC=CC=C1
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INCHI for HMDB0041950 (Nitrobenzene)

InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC6H5NO2
Average Molecular Weight123.1094
Monoisotopic Molecular Weight123.032028409
IUPAC Namenitrobenzene
Traditional Namenitrobenzene
CAS Registry Number98-95-3
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
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • Organic nitro compound
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point5.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.09 mg/mL at 25 °CNot Available
LogP1.85Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7138
KEGG Compound IDC06813
BioCyc IDBENZENE-NO2
BiGG IDNot Available
Wikipedia LinkNitrobenzene
METLIN IDNot Available
PubChem Compound7416
PDB IDNot Available
ChEBI ID27798
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sierra-Santoyo A, Hernandez M, Albores A, Cebrian ME: Sex-dependent regulation of hepatic cytochrome P-450 by DDT. Toxicol Sci. 2000 Mar;54(1):81-7. [PubMed:10746934 ]
  2. Lee KJ, Woo ER, Choi CY, Shin DW, Lee DG, You HJ, Jeong HG: Protective effect of acteoside on carbon tetrachloride-induced hepatotoxicity. Life Sci. 2004 Jan 9;74(8):1051-64. [PubMed:14672760 ]
  3. Ying ST, Huang WF, Tian LY, Shen XY: [Effects of Pb(NO3)2 and cetylpyridinium chloride on sorption of p-nitrophenol by sediment]. Huan Jing Ke Xue. 2006 Jul;27(7):1373-6. [PubMed:16881312 ]
  4. Wueweera JB, Gandolfi AJ, Badger DA, Sipes IG, Brendel K: Vitamin A potentiation of vinylidene chloride hepatotoxicity in rats and precision-cut rat liver slices. Fundam Appl Toxicol. 1996 Nov;34(1):73-83. [PubMed:8937894 ]