5-(1-methyl-5-oxopyrrolidin-2-yl)pyridine-3-carboxylic acid

• ChemBase ID: 164983
• Molecular Formular: C11H12N2O3
• Molecular Mass: 220.22458
• Monoisotopic Mass: 220.08479225
• SMILES: c1c(cc(cn1)C1CCC(=O)N1C)C(=O)O
• Canonical SMILES: O=C1CCC(N1C)c1cncc(c1)C(=O)O
• InChI: InChI=1S/C11H12N2O3/c1-13-9(2-3-10(13)14)7-4-8(11(15)16)6-12-5-7/h4-6,9H,2-3H2,1H3,(H,15,16)
• InChIKey: BRPNTJZYIZZLBE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(1-methyl-5-oxopyrrolidin-2-yl)pyridine-3-carboxylic acid
• IUPAC Traditional name: 5-(1-methyl-5-oxopyrrolidin-2-yl)pyridine-3-carboxylic acid
• Synonyms: rac 1-Methyl-2-pyrrolidinone-5-(3-pyridinyl)carboxylic Acid; 5-(1-Methyl-5-oxo-2-pyrrolidinyl)-3-pyridinecarboxylic Acid; rac-Cotinine 3-Carboxylic Acid

Database IDs

• CAS Number: 1246815-18-8
• PubChem SID: 162259116
• PubChem CID: 71314984

CALCULATED PROPERTIES

• Acid pKa: 4.00945
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.8981595
• LogD (pH = 7.4): -3.420769
• Log P: -0.5542404
• Molar Refractivity: 56.5367 cm^3
• Polarizability: 21.50289 Å^3
• Polar Surface Area: 70.5 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C725140

A Nornicotine analog to use as haptens for immunoassays. The compound is present in tobacco and tobacco smoke. Carcinogen.

REFERENCES

• Tsuda, K., et al.: Pharm. Bull., 1, 142 (1953)
• Daggett, L.P., et al.: Neuropharmacology, 34, 871 (1953)