ammonium 4-hydroxy-4-(pyridin-3-yl)butanoate

• ChemBase ID: 177180
• Molecular Formular: C9H14N2O3
• Molecular Mass: 198.21906
• Monoisotopic Mass: 198.10044232
• SMILES: c1cncc(c1)C(CCC(=O)[O-])O.[NH4+]
• Canonical SMILES: [O-]C(=O)CCC(c1cccnc1)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
• InChIKey: HOAONDNONYHPCP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium 4-hydroxy-4-(pyridin-3-yl)butanoate
• IUPAC Traditional name: ammonium 4-hydroxy-4-(pyridin-3-yl)butanoate
• Synonyms: γ-Hydroxy-3-pyridinebutanoic Acid; 4-Hydroxy-4-(3-pyridyl)butyric Acid Ammonium Salt; 4-(3-Pyridyl)-4-hydroxybutyric Acid Ammonium Salt; γ-(3-Pyridyl)-γ-hydroxy-butyric Acid Ammonium Salt; 1-(3-Pyridyl)-1-butanol-4-carboxylic Acid Ammonium Salt

Database IDs

• PubChem SID: 164233090
• PubChem CID: 45040305

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

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: Off-White to Pale Yellow Waxy Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P992550

A 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)