4-[(2H3)methyl(nitroso)amino]-4-(pyridin-3-yl)butanoic acid

• ChemBase ID: 174138
• Molecular Formular: C10H13N3O3
• Molecular Mass: 223.22852
• Monoisotopic Mass: 223.09569129
• SMILES: c1ccncc1C(CCC(=O)O)N(C)N=O
• Canonical SMILES: O=NN(C(c1cccnc1)CCC(=O)O)C
• InChI: InChI=1S/C10H13N3O3/c1-13(12-16)9(4-5-10(14)15)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3,(H,14,15)
• InChIKey: NZSNJPDBPMIBSP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(^2H₃)methyl(nitroso)amino]-4-(pyridin-3-yl)butanoic acid
• IUPAC Traditional name: 4-[(^2H₃)methyl(nitroso)amino]-4-(pyridin-3-yl)butanoic acid
• Synonyms: Iso-NNAC-d3; γ-[(Methyl-d3)nitrosoamino]-3-pyridinebutanoic Acid; 4-(Methylnitrosamino-d3)-4-(3-pyridyl)butyric Acid

Database IDs

• PubChem SID: 164230048
• PubChem CID: 71750533

CALCULATED PROPERTIES

• Acid pKa: 3.8828807
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.9141791
• LogD (pH = 7.4): -2.5194442
• Log P: -0.2796642
• Molar Refractivity: 57.7154 cm^3
• Polarizability: 21.688103 Å^3
• Polar Surface Area: 82.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M325754

Labelled Iso-NNAC. It was found in cigarette tobacco and mainstream cigarette smoke. Carcinogenic.

REFERENCES

• Djordjevic, M.V., et al.: Carcinogenesis, 10, 1725 (1989)