1-Nitronaphthalene (T3D4944)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (4)XML
Targets (4)
Record Information
Version2.0
Creation Date2014-09-17 20:01:34 UTC
Update Date2014-12-24 20:27:00 UTC
Accession NumberT3D4944
Identification
Common Name1-Nitronaphthalene
ClassSmall Molecule
Description1-nitronaphthalene (1-NN) is a common air pollutant in urban areas. It can react with ozone and will form reactive electrophiles that have been shown to bind covalently to specific proteins. 1-Nitronaphthalene is synthesized by the action of a mixture of nitric and sulfuric acids on finely ground naphthalene. 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. 1-NN is also found in the gas phase of diesel exhaust, making it one of the more common airborne pollutants. 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.
Compound Type
  • Aromatic Hydrocarbon
  • Dye
  • Industrial Precursor/Intermediate
  • Lachrymator
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
alpha-Nitronaphthalene
Nitrol
Chemical FormulaC10H7NO2
Average Molecular Mass173.168 g/mol
Monoisotopic Mass173.048 g/mol
CAS Registry Number86-57-7
IUPAC Name1-nitronaphthalene
Traditional Namenitrol
SMILESO=N(=O)C1=CC=CC2=CC=CC=C12
InChI IdentifierInChI=1S/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H
InChI KeyInChIKey=RJKGJBPXVHTNJL-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Lung
  • Nasal Passages
Pathways
NameSMPDB LinkKEGG Link
Metabolic PathwaysNot AvailableNot Available
Homologous recombinationNot Availablemap03440
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceYellow needles or green-red to brown crystals.
Experimental Properties
PropertyValue
Melting Point61.5°C
Boiling Point304°C
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9600000000-bdf73b19a48ec1965ff92017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9600000000-bdf73b19a48ec1965ff92018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-2900000000-0140e7cd9d0b52504c9a2017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-33ee06a9c8b5b2d7d4a62016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9c34bb8dbc81213babf92016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-1900000000-b7e76a0a748be59403372016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-b7779eb83652f78c0ed92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-e703c93ccd2f202675fd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-1900000000-244213ab51d311f2343b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-e4aa4846c14db133ae002021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-e4aa4846c14db133ae002021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0900000000-e4aa4846c14db133ae002021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-7dd52f7617ae35e45cc42021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-7dd52f7617ae35e45cc42021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-7900000000-bc620efb4831b63180402021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-4e9a24f4a3738ec10d6f2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureInhalation
Mechanism of Toxicity1-Nitronaphthalene and its reactive products specifically targets the airway epithelium. Its toxicity is synergized by prior long-term ozone exposure. 1-NN appears to specifically target peroxiredoxin 6 and biliverdin reductase as well as the N-terminal region of calreticulin.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesIndustrial intermediate, used in production of dyes, found in diesel exhast, air pollutant
Minimum Risk LevelNot Available
Health EffectsHealth effects: May cause eye, skin, respiratory tract and digestive tract irritation. Chronic exposure may cause cancer (based on animal studies).
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound IDNot Available
ChEMBL IDCHEMBL165373
ChemSpider ID6588
KEGG ID6849
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4944.pdf
General References
  1. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
  2. Deering-Rice CE, Romero EG, Shapiro D, Hughen RW, Light AR, Yost GS, Veranth JM, Reilly CA: Electrophilic components of diesel exhaust particles (DEP) activate transient receptor potential ankyrin-1 (TRPA1): a probable mechanism of acute pulmonary toxicity for DEP. Chem Res Toxicol. 2011 Jun 20;24(6):950-9. doi: 10.1021/tx200123z. Epub 2011 May 25. [21591660 ]
Target Details
2. Biliverdin reductase A
General Function:
Zinc ion binding
Specific Function:
Reduces the gamma-methene bridge of the open tetrapyrrole, biliverdin IX alpha, to bilirubin with the concomitant oxidation of a NADH or NADPH cofactor.
Gene Name:
BLVRA
Uniprot ID:
P53004
Molecular Weight:
33428.225 Da
Target Details
3. Calreticulin
General Function:
Zinc ion binding
Specific Function:
Calcium-binding chaperone that promotes folding, oligomeric assembly and quality control in the endoplasmic reticulum (ER) via the calreticulin/calnexin cycle. This lectin interacts transiently with almost all of the monoglucosylated glycoproteins that are synthesized in the ER. Interacts with the DNA-binding domain of NR3C1 and mediates its nuclear export. Involved in maternal gene expression regulation. May participate in oocyte maturation via the regulation of calcium homeostasis (By similarity).
Gene Name:
CALR
Uniprot ID:
P27797
Molecular Weight:
48141.2 Da
Target Details
4. Peroxiredoxin-6
General Function:
Ubiquitin protein ligase binding
Specific Function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular Weight:
25034.715 Da