1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-(2H3)methyl-5-oxopyrrolidin-2-yl]-1λ5-pyridin-1-ylium

• ChemBase ID: 164991
• Molecular Formular: C16H20N2O7
• Molecular Mass: 352.3392
• Monoisotopic Mass: 352.12705099
• SMILES: C1C[C@H](N(C1=O)C)c1c[n+](ccc1)[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-]
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H]([n+]2cccc(c2)[C@@H]2CCC(=O)N2C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H20N2O7/c1-17-9(4-5-10(17)19)8-3-2-6-18(7-8)15-13(22)11(20)12(21)14(25-15)16(23)24/h2-3,6-7,9,11-15,20-22H,4-5H2,1H3/t9-,11-,12-,13+,14-,15+/m0/s1
• InChIKey: XWZCZWKUGIQPJD-LKUTUIMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-(^2H₃)methyl-5-oxopyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-(^2H₃)methyl-5-oxopyrrolidin-2-yl]-1λ^5-pyridin-1-ylium
• Synonyms: CNGN-β-D-glucopyranuronosyl-(r,s)-(-)-cotinium, Methyl-d3 inner salt; Cotinine-d3 N-β-D-Glucuronide

Database IDs

• PubChem SID: 162259124
• PubChem CID: 71314994

CALCULATED PROPERTIES

• Acid pKa: 2.8463566
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -6.05522
• LogD (pH = 7.4): -6.055902
• Log P: -5.8264213
• Molar Refractivity: 93.8025 cm^3
• Polarizability: 32.83518 Å^3
• Polar Surface Area: 134.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 156-158°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C725180

A major metabolite of Nicotine in humans. Carcinogen.