1-[(2S,3S,4R)-6-carboxylato-3,4-dihydroxy-3,4-dihydro-2H-pyran-2-yl]-3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]-1λ5-pyridin-1-ylium

• ChemBase ID: 164986
• Molecular Formular: C16H18N2O6
• Molecular Mass: 334.32392
• Monoisotopic Mass: 334.11648631
• SMILES: C1C[C@H](N(C1=O)C)c1c[n+](ccc1)[C@H]1OC(=C[C@H]([C@H]1O)O)C(=O)[O-]
• Canonical SMILES: O[C@@H]1C=C(O[C@@H]([C@@H]1O)[n+]1cccc(c1)[C@@H]1CCC(=O)N1C)C(=O)[O-]
• InChI: InChI=1S/C16H18N2O6/c1-17-10(4-5-13(17)20)9-3-2-6-18(8-9)15-14(21)11(19)7-12(24-15)16(22)23/h2-3,6-8,10-11,14-15,19,21H,4-5H2,1H3/t10-,11+,14-,15-/m0/s1
• InChIKey: DXCAURCQPPWRAO-JLUCKKNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,3S,4R)-6-carboxylato-3,4-dihydroxy-3,4-dihydro-2H-pyran-2-yl]-3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2S,3S,4R)-6-carboxylato-3,4-dihydroxy-3,4-dihydro-2H-pyran-2-yl]-3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: N-(β-D-4-Deoxy-4,5-didehydroglucopyranosyl)uronate, Cotinium Inner Salt; Cotinine N-(4-Deoxy-4,5-didehydro)-β-D-glucuronide

Database IDs

• CAS Number: 146275-15-2
• PubChem SID: 162259119
• PubChem CID: 29976417

CALCULATED PROPERTIES

• Acid pKa: 2.9024894
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -5.3165417
• LogD (pH = 7.4): -5.316974
• Log P: -5.0874925
• Molar Refractivity: 94.1635 cm^3
• Polarizability: 31.90013 Å^3
• Polar Surface Area: 114.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Crystalline Solid
• Melting Point: 153-156°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - C725160

A major metabolite of Nicotine in humans. Carcinogen.

REFERENCES

• Benowitz, N., et al.: Clin. Pharmacol. Ther., 56, 483 (1994)
• Nakajima, M., et al.: Drug Metab. Dispos., 24, 1212 (1994)
• Messina, E., et al.: J. Pharmacol. Exp. Ther., 282, 1608 (1994)
• Oscarson, M., et al.: Hum. Mutat., 20, 275 (1994)