methyl (2R,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylate

• ChemBase ID: 164985
• Molecular Formular: C12H14N2O3
• Molecular Mass: 234.25116
• Monoisotopic Mass: 234.10044232
• SMILES: c1ccc(cn1)[C@H]1[C@H](CC(=O)N1C)C(=O)OC
• Canonical SMILES: COC(=O)[C@H]1CC(=O)N([C@H]1c1cccnc1)C
• InChI: InChI=1S/C12H14N2O3/c1-14-10(15)6-9(12(16)17-2)11(14)8-4-3-5-13-7-8/h3-5,7,9,11H,6H2,1-2H3/t9-,11-/m0/s1
• InChIKey: LXSYCOKNUBLDNJ-ONGXEEELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylate
• IUPAC Traditional name: methyl (2R,3S)-1-methyl-5-oxo-2-(pyridin-3-yl)pyrrolidine-3-carboxylate
• Synonyms: (2R,3R)-rel-1-Methyl-5-oxo-2-(3-pyridinyl)-3-pyrrolidinecarboxylic Acid Methyl Ester; trans-1-Methyl-5-oxo-2-(3-pyridinyl)-3-pyrrolidinecarboxylic Acid Methyl Ester; rac trans-4-Cotinine Carboxylic Acid Methyl Ester

Database IDs

• CAS Number: 135028-97-6
• PubChem SID: 162259118
• PubChem CID: 71314985

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.33268094
• LogD (pH = 7.4): -0.2657613
• Log P: -0.26481944
• Molar Refractivity: 60.1355 cm^3
• Polarizability: 23.600344 Å^3
• Polar Surface Area: 59.5 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - C725155

Cotinine derivative. A chemokine receptor.

REFERENCES

• Lucchesi, B., et al.: Clin. Pharmacol. Ther., 8, 789 (1967)
• Pitas, R., et al.: J. Cell Biol., 100, 103 (1985) Sanderson, S; J Med Chem 1994, 37, 3171,,,13) Ulrich, J; J Immunol 2000, 164, 5492