(3R,5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

• ChemBase ID: 170374
• Molecular Formular: C10H12N2O2
• Molecular Mass: 192.21448
• Monoisotopic Mass: 192.08987763
• SMILES: c1ccc(cn1)[C@@H]1C[C@H](C(=O)N1C)O
• Canonical SMILES: O=C1[C@H](O)C[C@H](N1C)c1cccnc1
• InChI: InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9+/m0/s1
• InChIKey: XOKCJXZZNAUIQN-DTWKUNHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
• IUPAC Traditional name: (3R,5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
• Synonyms: (3R,5S)-3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone; (3'R,5'S)-3'-Hydroxycotinine; Hydroxycotinine; (3S-trans)-3-Hydroxycotinine; trans-3'-Hydroxy Cotinine

Database IDs

• CAS Number: 34834-67-8
• PubChem SID: 164226284
• PubChem CID: 107963

CALCULATED PROPERTIES

• Acid pKa: 13.107323
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.8017361
• LogD (pH = 7.4): -0.734178
• Log P: -0.7332254
• Molar Refractivity: 50.7291 cm^3
• Polarizability: 19.751343 Å^3
• Polar Surface Area: 53.43 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Water
• Apperance: Off-White to Pale-Yellow Solid
• Melting Point: 107-109°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H924500

A metabolite of Nicotine. Carcinogen.

REFERENCES

• Horning, E., et al.: Life Sci., 13, 1331 (1973)
• Desai, D., et al.: Chem. Res. Toxicol., 3, 47 (1973)
• Kitagawa, K., et al.: J. Biol. Chem., 276, 17830 (1973)