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Showing metabocard for 1-nitronaphthalene (HMDB0062188)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-02-24 01:29:34 UTC
Update Date2023-02-21 17:30:40 UTC
HMDB IDHMDB0062188
Secondary Accession Numbers
  • HMDB62188
Metabolite Identification
Common Name1-nitronaphthalene
Description1-nitronaphthalene, also known as nitrol, belongs to the class of organic compounds known as nitronaphthalenes. These are polycyclic aromatic compounds containing a naphthalene moiety substituted by one or more nitro groups. 1-Nitronaphthalene is synthesized by the action of a mixture of nitric and sulfuric acids on finely ground naphthalene. 1-nitronaphthalene is possibly neutral. 1-nitronaphthalene is a potentially toxic compound. 1-nitronaphthalene (1-NN) is a common air pollutant in urban areas. 1-NN appears to specifically target peroxiredoxin 6 and biliverdin reductase as well as the N-terminal region of calreticulin. 1-Nitronaphthalene and its reactive products specifically targets the airway epithelium. 1-NN is also found in the gas phase of diesel exhaust, making it one of the more common airborne pollutants. 1-nitronaphthalene is used as a chemical intermediate in the manufacture of dyes (drugs, perfumes, rubber chemicals, tanning agents and pesticides) and as a fluorescence quencher for mineral oils. It has been detected in some carbon blacks as well as in particulate exhaust of diesel engines and has been found at low concentrations in ambient air. It can react with ozone and will form reactive electrophiles that have been shown to bind covalently to specific proteins. Chronic exposure may cause cancer (based on animal studies). Its toxicity is synergized by prior long-term ozone exposure. Health effects: May cause eye, skin, respiratory tract and digestive tract irritation.
Structure
Data?1677000640
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0062188 (1-nitronaphthalene)

  Mrv1652305261923512D          

 13 14  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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0062188 (1-nitronaphthalene)

HMDB0062188
     RDKit          3D
1-nitronaphthalene
 20 21  0  0  0  0  0  0  0  0999 V2000
   -2.8779    2.3514    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045    2.0528    0.4689 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0011    3.0461    1.0362 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2906    0.7264    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -0.3136    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -1.6121    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5715   -1.9552   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688   -0.9447   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -1.3032   -0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924   -0.3681   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371    0.9359   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    1.3444    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    0.4024    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -0.0456    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615   -2.3715    0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593   -2.9967   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9492   -2.3372   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023   -0.6763   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    1.6866   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    2.3781    0.1801 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 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  4  1  0
 13  8  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  CHG  2   2   1   3  -1
M  END
Download

3D SDF for HMDB0062188 (1-nitronaphthalene)

  Mrv1652305261923512D          

 13 14  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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062188

> <DATABASE_NAME>
hmdb

> <SMILES>
O=N(=O)C1=CC=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H

> <INCHI_KEY>
RJKGJBPXVHTNJL-UHFFFAOYSA-N

> <FORMULA>
C10H7NO2

> <MOLECULAR_WEIGHT>
173.1681

> <EXACT_MASS>
173.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.855790103888978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-nitronaphthalene

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.9027067619999998

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
45.82

> <JCHEM_REFRACTIVITY>
49.8329

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitrol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0062188 (1-nitronaphthalene)

HMDB0062188
     RDKit          3D
1-nitronaphthalene
 20 21  0  0  0  0  0  0  0  0999 V2000
   -2.8779    2.3514    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045    2.0528    0.4689 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0011    3.0461    1.0362 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2906    0.7264    0.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -0.3136    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -1.6121    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5715   -1.9552   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688   -0.9447   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857   -1.3032   -0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924   -0.3681   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3371    0.9359   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390    1.3444    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346    0.4024    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -0.0456    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615   -2.3715    0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593   -2.9967   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9492   -2.3372   -0.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023   -0.6763   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1090    1.6866   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    2.3781    0.1801 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 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  4  1  0
 13  8  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  CHG  2   2   1   3  -1
M  END
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PDB for HMDB0062188 (1-nitronaphthalene)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    5    7                                                       
CONECT    4    1    8                                                       
CONECT    5    3    8                                                       
CONECT    6    2    9                                                       
CONECT    7    3   10                                                       
CONECT    8    4    5    9                                                  
CONECT    9    6    8   10                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0062188 (1-nitronaphthalene)

COMPND    HMDB0062188
HETATM    1  O1  UNL     1      -2.878   2.351   0.083  1.00  0.00           O  
HETATM    2  N1  UNL     1      -1.705   2.053   0.469  1.00  0.00           N1+
HETATM    3  O2  UNL     1      -1.001   3.046   1.036  1.00  0.00           O1-
HETATM    4  C1  UNL     1      -1.291   0.726   0.257  1.00  0.00           C  
HETATM    5  C2  UNL     1      -2.238  -0.314   0.242  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.889  -1.612   0.038  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.572  -1.955  -0.165  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.369  -0.945  -0.154  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.686  -1.303  -0.367  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.692  -0.368  -0.383  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.337   0.936  -0.178  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.039   1.344   0.039  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.035   0.402   0.055  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.264  -0.046   0.400  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.662  -2.371   0.036  1.00  0.00           H  
HETATM   16  H3  UNL     1      -0.259  -2.997  -0.329  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.949  -2.337  -0.526  1.00  0.00           H  
HETATM   18  H5  UNL     1       3.702  -0.676  -0.548  1.00  0.00           H  
HETATM   19  H6  UNL     1       3.109   1.687  -0.186  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.840   2.378   0.180  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   16
CONECT    8    9    9   13
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   12   19
CONECT   12   13   13   20
END
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SMILES for HMDB0062188 (1-nitronaphthalene)

O=N(=O)C1=CC=CC2=CC=CC=C12
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INCHI for HMDB0062188 (1-nitronaphthalene)

InChI=1S/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
alpha-NitronaphthaleneChEBI
NitrolChEBI
a-NitronaphthaleneGenerator
Α-nitronaphthaleneGenerator
Chemical FormulaC10H7NO2
Average Molecular Weight173.1681
Monoisotopic Molecular Weight173.047678473
IUPAC Name1-nitronaphthalene
Traditional Namenitrol
CAS Registry Number86-57-7
SMILES
O=N(=O)C1=CC=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
InChI KeyRJKGJBPXVHTNJL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitronaphthalenes. These are polycyclic aromatic compounds containing a naphthalene moiety substituted by one or more nitro groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNitronaphthalenes
Direct ParentNitronaphthalenes
Alternative Parents
Substituents
  • 1-nitronaphthalene
  • 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 homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.043 g/lALOGPS
LogP3.20ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.2ALOGPS
logP2.9ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.82 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability16.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 IDNot Available
KEGG Compound IDC14040
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6849
PDB IDNot Available
ChEBI ID34104
Food Biomarker OntologyNot Available
VMH IDM00545
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available