methyl (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: 170380
• Molecular Formular: C17H20N2O7
• Molecular Mass: 364.3499
• Monoisotopic Mass: 364.12705099
• 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)OC)O)O
• Canonical SMILES: COC(=O)C1=C[C@@H]([C@@H]([C@@H](O1)O[C@@H]1C[C@H](N(C1=O)C)c1cccnc1)O)O
• InChI: InChI=1S/C17H20N2O7/c1-19-10(9-4-3-5-18-8-9)6-12(15(19)22)25-17-14(21)11(20)7-13(26-17)16(23)24-2/h3-5,7-8,10-12,14,17,20-21H,6H2,1-2H3/t10-,11-,12+,14+,17+/m0/s1
• InChIKey: CAVBICHEBRPWPW-IGXHCJPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (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: methyl (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 Methyl Ester

Database IDs

• CAS Number: 1217540-34-5
• PubChem SID: 164226290
• PubChem CID: 71748946

CALCULATED PROPERTIES

• Acid pKa: 12.346774
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.134141
• LogD (pH = 7.4): -1.066587
• Log P: -1.0656303
• Molar Refractivity: 88.1399 cm^3
• Polarizability: 34.595654 Å^3
• Polar Surface Area: 118.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 56-58°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H924523

A nicotine metabolite. Carcinogen.