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Record Information
Version1.0
Created at2009-01-29 12:50:38 UTC
Updated at2021-06-30 02:06:18 UTC
NP-MRD IDNP0000222
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone
Description4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (also known as NNK) is a potent tobacco-specific nitrosamine derived from nicotine. It plays a key role in human tobacco-related cancers (PMID:24830349 ). NNK is found in cured tobacco and is also produced during its burning or combustion in cigarettes. NNK is abundantly present in cigarette smoke (20-280 ng/cigarette). Electronic cigarettes (e-cigarettes) do not convert nicotine to NNK due to their lower operating temperatures. NNK is a procarcinogen. This means it must be activated by cytochrome P450 enzymes (CYP2A6 and CYP2B6) to become a carcinogen (PMID:24830349 ). NNK can also be activated by myeloperoxidase (MPO) and epoxide hydrolase (EPHX1). All activation processes lead to the formation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol from NNK, which is called NNAL (PMID:24830349 ). NNAL can be detoxified via glucuronidation via glucuronidases. Once NNK is activated to NNAL, this compound initiates a cascade of signalling pathways (for example ERK1/2, NFκB, PI3K/Akt, MAPK, FasL, K-ras), resulting in uncontrolled cellular proliferation and tumorigenesis. NNK is known as a mutagen and can cause point mutations that affect cell growth proliferation and differentiation. NNK also targets the SULT1A1, TGF-beta, and angiotensin II genes. NNK plays a key role in gene silencing, gene modification, and carcinogenesis. NNK has been implicated in tumour promotion by activating nicotinic acetylcholine receptors (nAChRs) and β-adrenergic receptors (β-AdrRs), leading to downstream activation of parallel signal transduction pathways that facilitate tumour progression (PMID:24830349 ). Antioxidants such as EGCG (from green tea) inhibit lung tumorigenesis by NNK.
Structure
Thumb
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 Mass207.2291 Da
Monoisotopic Mass207.10078 Da
IUPAC Name4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one
Traditional Namennk (carcinogen)
CAS Registry Number64091-91-4
SMILES
CN(CCCC(=O)C1=CC=CN=C1)N=O
InChI Identifier
InChI=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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-10View Spectrum
Species
Species of Origin
  • Animalia
  • 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
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point64 °CNot Available
    Boiling PointNot AvailableNot Available
    Water SolubilityNot AvailableNot Available
    LogPNot AvailableNot 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
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterYesChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0011603
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB028314
    KNApSAcK IDNot Available
    Chemspider ID43038
    KEGG Compound IDC16453
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNNK
    METLIN IDNot Available
    PubChem Compound47289
    PDB IDNot Available
    ChEBI ID32692
    Good Scents IDNot Available
    References
    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. [PubMed:8625495 ]
    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. [PubMed:24830349 ]