3-{4-[methyl(nitroso)amino]butanoyl}pyridin-1-ium-1-olate

• ChemBase ID: 174053
• Molecular Formular: C10H13N3O3
• Molecular Mass: 223.22852
• Monoisotopic Mass: 223.09569129
• SMILES: c1c[n+](cc(c1)C(=O)CCCN(C)N=O)[O-]
• Canonical SMILES: O=NN(CCCC(=O)c1ccc[n+](c1)[O-])C
• InChI: InChI=1S/C10H13N3O3/c1-12(11-15)6-3-5-10(14)9-4-2-7-13(16)8-9/h2,4,7-8H,3,5-6H2,1H3
• InChIKey: KRRWRVSPMYAJPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[methyl(nitroso)amino]butanoyl}pyridin-1-ium-1-olate
• IUPAC Traditional name: 3-{4-[methyl(nitroso)amino]butanoyl}pyridin-1-ium-1-olate
• Synonyms: 4-(Methylnitrosoamino)-1-(1-oxido-3-pyridinyl)-1-butanone; NNK-N-Oxide; 4-(Methylnitrosamino)-1-(3-pyridyl-N-oxide)-1-butanone; 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone N-Oxide

Database IDs

• CAS Number: 76014-82-9
• PubChem SID: 164229963
• PubChem CID: 156652

CALCULATED PROPERTIES

• Acid pKa: 15.204199
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.68194556
• LogD (pH = 7.4): -0.68132716
• Log P: -0.68131924
• Molar Refractivity: 60.9392 cm^3
• Polarizability: 21.6951 Å^3
• Polar Surface Area: 75.2 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: Off-White to Beige Solid
• Melting Point: 102-104°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M325760

A metabolite of the carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), (M32575), a tobacco-specific nitrosamine. Carcinogenic.

REFERENCES

• Hecht, S.S., et al.: Cancer Res., 40, 4144 (1980)
• Kutzer, C., et al.: J. Chromatog. Sci., 35, 1 (1980)
• Zimmerman, C., et al.: Carcinogenesis, 25, 1237 (1980)