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

• ChemBase ID: 164984
• Molecular Formular: C11H12N2O3
• Molecular Mass: 220.22458
• Monoisotopic Mass: 220.08479225
• SMILES: c1ccc(cn1)[C@H]1[C@H](CC(=O)N1C)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1CC(=O)N([C@H]1c1cccnc1)C
• InChI: InChI=1S/C11H12N2O3/c1-13-9(14)5-8(11(15)16)10(13)7-3-2-4-12-6-7/h2-4,6,8,10H,5H2,1H3,(H,15,16)/t8-,10-/m0/s1
• InChIKey: DEYLVDCFTICBTB-WPRPVWTQSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 161171-06-8
• PubChem SID: 162259117
• PubChem CID: 671218

CALCULATED PROPERTIES

• Acid pKa: 3.7754128
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.9685076
• LogD (pH = 7.4): -3.5595684
• Log P: -1.3200238
• Molar Refractivity: 55.3664 cm^3
• Polarizability: 21.528112 Å^3
• Polar Surface Area: 70.5 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Base; DMF; DMSO
• Apperance: White Solid
• Melting Point: 194-195°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C725150

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,,,