<i>N</i>'-Nitrosonornicotine (NNN) and 4-(<i>N</i>-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK) (CHEM016152)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:16:57 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016152
Identification
Common Name<i>N</i>'-Nitrosonornicotine (NNN) and 4-(<i>N</i>-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone (NNK)
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 1
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanoneChEBI
NNKChEBI
NNK (Carcinogen)ChEBI
4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanoneHMDB
4'-(Nitrosomethylamino)-1-(3-pyridyl)-1-butanoneHMDB
NNK CPDHMDB
4-(N-Nitrosomethylamino)-1-(3-pyridyl)-1-butanoneHMDB
4-(Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanoneHMDB
4-(Methylintrosamino)-1-(3-pyridyl)-1-butanoneHMDB
4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanoneHMDB
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanoneChEBI
Chemical FormulaC10H13N3O2
Average Molecular Mass207.229 g/mol
Monoisotopic Mass207.101 g/mol
CAS Registry Number64091-91-4
IUPAC Name4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one
Traditional Namennk (carcinogen)
SMILESCN(CCCC(=O)C1=CC=CN=C1)N=O
InChI IdentifierInChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3
InChI KeyFLAQQSHRLBFIEZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl alkyl ketones
Alternative Parents
Substituents
  • Aryl alkyl ketone
  • Pyridine
  • Heteroaromatic compound
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.09 g/LALOGPS
logP0.33ALOGPS
logP0.58ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)15.47ChemAxon
pKa (Strongest Basic)3.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area62.63 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity57.25 m³·mol⁻¹ChemAxon
Polarizability21.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9800000000-57c49f29c9d7332bea22Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1980000000-6eed182d10c9a03751b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3910000000-5fed6b71985ed1afcab4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001m-9600000000-1c5f7245d666beff11f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3390000000-e76106f4b8f69d27d9aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-9840000000-3d022ffc7f1a61b3d6d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9100000000-1782fbf95a7044f769a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0920000000-1d8ea81c64d584ea02d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-63e35eaa2366ca02b75dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-7900000000-5f96473ea00e041d2dccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-482b470c4a0ac6884d93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-9820000000-35e475a0c732f383cc12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9300000000-37d4b4467865dbb44ac7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011603
FooDB IDFDB028314
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNNK
Chemspider ID43038
ChEBI ID32692
PubChem Compound ID47289
Kegg Compound IDC16453
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Smith TJ, Guo Z, Guengerich FP, Yang CS: Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Carcinogenesis. 1996 Apr;17(4):809-13.
2. Xue J, Yang S, Seng S: Mechanisms of Cancer Induction by Tobacco-Specific NNK and NNN. Cancers (Basel). 2014 May 14;6(2):1138-56. doi: 10.3390/cancers6021138.