4-[methyl(nitroso)amino]-1-[(2,3,4,5,6-13C5)pyridin-3-yl](1-13C)butan-1-one

• ChemBase ID: 174135
• Molecular Formular: C10H13N3O2
• Molecular Mass: 213.18504903
• Monoisotopic Mass: 213.1209057
• SMILES: [13cH]1[13cH][13cH]n[13cH][13c]1[13C](=O)CCCN(C)N=O
• Canonical SMILES: O=NN(CCC[13C](=O)[13c]1[13cH][13cH][13cH]n[13cH]1)C
• InChI: 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/i2+1,4+1,6+1,8+1,9+1,10+1
• InChIKey: FLAQQSHRLBFIEZ-NXGVJODUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[methyl(nitroso)amino]-1-[(2,3,4,5,6-^1^3C₅)pyridin-3-yl](1-^1^3C)butan-1-one
• IUPAC Traditional name: 4-[methyl(nitroso)amino]-1-[(2,3,4,5,6-^1^3C₅)pyridin-3-yl](1-^1^3C)butan-1-one
• Synonyms: 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone-13C6; NNK-13C6; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-13C6

Database IDs

• PubChem SID: 164230045
• PubChem CID: 71750532

CALCULATED PROPERTIES

• Acid pKa: 15.470998
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.5703659
• LogD (pH = 7.4): 0.57872987
• Log P: 0.5788377
• Molar Refractivity: 57.2497 cm^3
• Polarizability: 21.183964 Å^3
• Polar Surface Area: 62.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M325749

Labelled NNK (M325750). This compound was present in the highest concentrations in smokeless tobacco out of the nitrosamines identified. It is likely to be important in the etiology of cancers of the lung, oral cavity, and pancreas in people who use taba

REFERENCES

• Koenigs, L., et al.: Drug Metab. Dispos., 25, 1407 (1997)
• Gu, J., et al.: Toxicol. Appl. Pharmacol., 165, 158 (1997)
• Jalas, J., et al.: Chem. Res. Toxicol., 18, 95(1997)
• Zhu, L., et al.: Drug Metab. Dispos., 34, 1672(1997)