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

• ChemBase ID: 170391
• Molecular Formular: C23H28N2O11
• Molecular Mass: 508.47522
• Monoisotopic Mass: 508.16930973
• 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)OC(=O)C)OC(=O)C)OC(=O)C
• 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]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C23H28N2O11/c1-11(26)32-17-18(33-12(2)27)20(34-13(3)28)23(36-19(17)22(30)31-5)35-16-9-15(25(4)21(16)29)14-7-6-8-24-10-14/h6-8,10,15-20,23H,9H2,1-5H3/t15-,16+,17-,18-,19-,20+,23+/m0/s1
• InChIKey: RQJMTVBLRLXVBC-ALZPROSGSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 164226301
• PubChem CID: 71748954

CALCULATED PROPERTIES

• Acid pKa: 19.110806
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): -0.78302675
• LogD (pH = 7.4): -0.715468
• Log P: -0.7145162
• Molar Refractivity: 115.2334 cm^3
• Polarizability: 47.104588 Å^3
• Polar Surface Area: 156.86 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - H924635

A derivative of Nicotine metabolite. Carcinogen.