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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-02-24 01:29:34 UTC
Update Date2022-03-07 03:17:49 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?1563866277
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
Disposition

Source

Route of exposure

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

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-167.62130932474
DeepCCS[M+Na]+142.90930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-nitronaphthaleneO=N(=O)C1=CC=CC2=CC=CC=C122546.9Standard polar33892256
1-nitronaphthaleneO=N(=O)C1=CC=CC2=CC=CC=C121562.5Standard non polar33892256
1-nitronaphthaleneO=N(=O)C1=CC=CC2=CC=CC=C121598.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-nitronaphthalene EI-B (Non-derivatized)splash10-0fb9-9600000000-bdf73b19a48ec1965ff92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-nitronaphthalene EI-B (Non-derivatized)splash10-0fb9-9600000000-bdf73b19a48ec1965ff92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-nitronaphthalene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2900000000-0140e7cd9d0b52504c9a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-nitronaphthalene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-nitronaphthalene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-4e9a24f4a3738ec10d6f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 10V, Positive-QTOFsplash10-00di-0900000000-33ee06a9c8b5b2d7d4a62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 20V, Positive-QTOFsplash10-014i-0900000000-9c34bb8dbc81213babf92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 40V, Positive-QTOFsplash10-0gi0-1900000000-b7e76a0a748be59403372016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 10V, Negative-QTOFsplash10-00di-0900000000-b7779eb83652f78c0ed92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 20V, Negative-QTOFsplash10-00di-0900000000-e703c93ccd2f202675fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 40V, Negative-QTOFsplash10-01b9-1900000000-244213ab51d311f2343b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 10V, Negative-QTOFsplash10-00di-0900000000-e4aa4846c14db133ae002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 20V, Negative-QTOFsplash10-00di-0900000000-e4aa4846c14db133ae002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 40V, Negative-QTOFsplash10-00di-0900000000-e4aa4846c14db133ae002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 10V, Positive-QTOFsplash10-00di-0900000000-7dd52f7617ae35e45cc42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 20V, Positive-QTOFsplash10-00di-0900000000-7dd52f7617ae35e45cc42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-nitronaphthalene 40V, Positive-QTOFsplash10-0fb9-7900000000-bc620efb4831b63180402021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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