ammonium 4-hydroxy-4-[(2,3,4,5,6-13C5)pyridin-3-yl](4-13C)butanoate

• ChemBase ID: 177181
• Molecular Formular: C9H14N2O3
• Molecular Mass: 204.17498903
• Monoisotopic Mass: 204.12057135
• SMILES: [13cH]1[13cH]n[13cH][13c]([13cH]1)[13CH](CCC(=O)[O-])O.[NH4+]
• Canonical SMILES: [O-]C(=O)CC[13CH]([13c]1[13cH][13cH][13cH]n[13cH]1)O.[NH4+]
• InChI: InChI=1S/C9H11NO3.H3N/c11-8(3-4-9(12)13)7-2-1-5-10-6-7;/h1-2,5-6,8,11H,3-4H2,(H,12,13);1H3/i1+1,2+1,5+1,6+1,7+1,8+1
• InChIKey: HOAONDNONYHPCP-HHULZBBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium 4-hydroxy-4-[(2,3,4,5,6-^1^3C₅)pyridin-3-yl](4-^1^3C)butanoate
• IUPAC Traditional name: ammonium 4-hydroxy-4-[(2,3,4,5,6-^1^3C₅)pyridin-3-yl](4-^1^3C)butanoate
• Synonyms: γ-Hydroxy-3-pyridinebutanoic Acid-13C6; 4-Hydroxy-4-(3-pyridyl)butyric Acid-13C6 Ammonium Salt; 4-(3-Pyridyl)-4-hydroxybutyric Acid-13C6 Ammonium Salt; γ-(3-Pyridyl)-γ-hydroxybutyric Acid-13C6 Ammonium Salt; 1-(3-Pyridyl)-1-butanol-4-carboxylic Acid-13C6 Ammonium Salt

Database IDs

• PubChem SID: 164233091
• PubChem CID: 71751893

CALCULATED PROPERTIES

• Acid pKa: 3.837264
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.47164
• LogD (pH = 7.4): -3.0828562
• Log P: -0.80308247
• Molar Refractivity: 56.7633 cm^3
• Polarizability: 17.849583 Å^3
• Polar Surface Area: 73.25 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P992552

A labelled metabolite of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), (M325750), a major carcinogen, it is present in cigarette smoke.

REFERENCES

• Hecht, S., et al.: Chem. Res. Toxicol., 11, 559 (1998)
• Hecht, S., et al.: Carcinogenesis, 23, 907 (1998)
• Sasco, A., et al.: Lung Cancer, 45, S3 (1998)