sodium (2R,3R,4S)-3,4-dihydroxy-2-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}-3,4-dihydro-2H-pyran-6-carboxylate

• ChemBase ID: 170379
• Molecular Formular: C16H17N2NaO7
• Molecular Mass: 372.30515
• Monoisotopic Mass: 372.09334518
• SMILES: [C@H]1(C[C@H](N(C1=O)C)c1cnccc1)O[C@H]1[C@H]([C@H](C=C(O1)C(=O)[O-])O)O.[Na+]
• Canonical SMILES: O[C@H]1C=C(O[C@H]([C@H]1O)O[C@@H]1C[C@H](N(C1=O)C)c1cccnc1)C(=O)[O-].[Na+]
• InChI: InChI=1S/C16H18N2O7.Na/c1-18-9(8-3-2-4-17-7-8)5-11(14(18)21)24-16-13(20)10(19)6-12(25-16)15(22)23;/h2-4,6-7,9-11,13,16,19-20H,5H2,1H3,(H,22,23);/q;+1/p-1/t9-,10-,11+,13+,16+;/m0./s1
• InChIKey: XVBSGNAOKDDEMA-DGJRYGEHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,3R,4S)-3,4-dihydroxy-2-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: sodium (4S,5R,6R)-4,5-dihydroxy-6-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: trans-3'-Hydroxy Cotinine-O-(4-deoxy-4,5-didehydro)-β-D-glucuronide Sodium Salt

Database IDs

• PubChem SID: 164226289
• PubChem CID: 71748944

CALCULATED PROPERTIES

• Acid pKa: 3.2887642
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.2767675
• LogD (pH = 7.4): -4.735636
• Log P: -2.5610414
• Molar Refractivity: 94.2079 cm^3
• Polarizability: 32.42307 Å^3
• Polar Surface Area: 132.25 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 185-188°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - H924520

A Nicotine (N412420) metabolite. Carcinogen.