Record Information
Version1.0
Creation date2011-09-21 01:37:48 UTC
Update date2015-10-09 22:33:26 UTC
Primary IDFDB028314
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone
Description4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a potent tobacco-specific nitrosamine in animals. It has been suggested to play a role in human tobacco-related cancers. P450 1A2 catalyzed the formation of keto alcohol and 4-oxo-1-(3-pyridyl)-1-butanone (keto aldehyde) from NNK, with the keto alcohol being the major metabolite. Phenethyl isothiocyanate (PEITC0 is an effective inhibitor of the carcinogenicity or toxicity of chemicals that are activated by P450 1A2.( PMID: 8625495) [HMDB]
CAS Number64091-91-4
Structure
Thumb
Synonyms
SynonymSource
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
NNK (carcinogen)hmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H13N3O2
IUPAC name4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one
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
Isomeric SMILESCN(CCCC(=O)C1=CC=CN=C1)N=O
Average Molecular Weight207.2291
Monoisotopic Molecular Weight207.100776675
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9800000000-57c49f29c9d7332bea22Spectrum
Predicted GC-MS4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1980000000-6eed182d10c9a03751b72016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3910000000-5fed6b71985ed1afcab42016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001m-9600000000-1c5f7245d666beff11f22016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3390000000-e76106f4b8f69d27d9aa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-9840000000-3d022ffc7f1a61b3d6d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9100000000-1782fbf95a7044f769a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0920000000-1d8ea81c64d584ea02d12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-63e35eaa2366ca02b75d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-7900000000-5f96473ea00e041d2dcc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-482b470c4a0ac6884d932021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-9820000000-35e475a0c732f383cc122021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9300000000-37d4b4467865dbb44ac72021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID43038
ChEMBL IDCHEMBL2311069
KEGG Compound IDC16453
Pubchem Compound ID47289
Pubchem Substance IDNot Available
ChEBI ID32692
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11603
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID0QA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Corticosteroid 11-beta-dehydrogenase isozyme 1HSD11B1P28845
Carbonyl reductase [NADPH] 1CBR1P16152
Carbonyl reductase [NADPH] 3CBR3O75828
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference