methyl (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 170389
• Molecular Formular: C17H22N2O8
• Molecular Mass: 382.36518
• Monoisotopic Mass: 382.13761567
• SMILES: [C@H]1(C[C@H](N(C1=O)C)c1cnccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)OC)O)O)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](O[C@@H]2C[C@H](N(C2=O)C)c2cccnc2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C17H22N2O8/c1-19-9(8-4-3-5-18-7-8)6-10(15(19)23)26-17-13(22)11(20)12(21)14(27-17)16(24)25-2/h3-5,7,9-14,17,20-22H,6H2,1-2H3/t9-,10+,11-,12-,13+,14-,17+/m0/s1
• InChIKey: GZHFHRDHYAKPJY-UAPWGZBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5S)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylate
• Synonyms: trans-3'-Hydroxycotinine-O-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 164226299
• PubChem CID: 71748953

CALCULATED PROPERTIES

• Acid pKa: 12.174725
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.106403
• LogD (pH = 7.4): -2.0388515
• Log P: -2.0378923
• Molar Refractivity: 87.7789 cm^3
• Polarizability: 35.532665 Å^3
• Polar Surface Area: 138.65 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 86-90°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H924560

A Nicotine metabolite. Carcinogen.