1-(6-hydroxypyridin-3-yl)-4-[methyl(nitroso)amino]butan-1-one

• ChemBase ID: 174052
• Molecular Formular: C10H13N3O3
• Molecular Mass: 223.22852
• Monoisotopic Mass: 223.09569129
• SMILES: c1cc(ncc1C(=O)CCCN(C)N=O)O
• Canonical SMILES: O=NN(CCCC(=O)c1ccc(nc1)O)C
• InChI: InChI=1S/C10H13N3O3/c1-13(12-16)6-2-3-9(14)8-4-5-10(15)11-7-8/h4-5,7H,2-3,6H2,1H3,(H,11,15)
• InChIKey: NIBWRJVURQTOPI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(6-hydroxypyridin-3-yl)-4-[methyl(nitroso)amino]butan-1-one
• IUPAC Traditional name: 1-(6-hydroxypyridin-3-yl)-4-[methyl(nitroso)amino]butan-1-one
• Synonyms: 5-[4-(Methylnitrosoamino)-1-oxobutyl]-2(1H)-pyridinone; 6-Hydroxy-NNK; 1-(1,6-Dihydro-6-oxo-3-pyridinyl)-4-(methylnitrosoamino)-1-butanone; 4-(Methylnitrosamino)-1-[3-(6-hydroxypyridyl)-1-butanone

Database IDs

• CAS Number: 151028-45-4
• PubChem SID: 164229962
• PubChem CID: 71750497

CALCULATED PROPERTIES

• Acid pKa: 9.588676
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.8690552
• LogD (pH = 7.4): 0.8669548
• Log P: 0.8697299
• Molar Refractivity: 59.5441 cm^3
• Polarizability: 21.834995 Å^3
• Polar Surface Area: 82.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M325758

A metabolite of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) (M325750). Carcinogenic.

REFERENCES

• Desai, D., et al.: Chem. Res. Toxicol., 6, 794 (1993)