methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[4-(2-{[(tert-butoxy)carbonyl](methyl)amino}-1-(1-hydroxycyclohexyl)ethyl)phenoxy]oxane-2-carboxylate

• ChemBase ID: 162482
• Molecular Formular: C33H47NO13
• Molecular Mass: 665.72518
• Monoisotopic Mass: 665.30474057
• SMILES: c1cc(ccc1C(C1(CCCCC1)O)CN(C)C(=O)OC(C)(C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)C(C2(O)CCCCC2)CN(C(=O)OC(C)(C)C)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C33H47NO13/c1-19(35)42-25-26(43-20(2)36)28(44-21(3)37)30(46-27(25)29(38)41-8)45-23-14-12-22(13-15-23)24(33(40)16-10-9-11-17-33)18-34(7)31(39)47-32(4,5)6/h12-15,24-28,30,40H,9-11,16-18H2,1-8H3/t24?,25-,26-,27-,28+,30+/m0/s1
• InChIKey: GIOIVGCHTZDGOM-ZURIANFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[4-(2-{[(tert-butoxy)carbonyl](methyl)amino}-1-(1-hydroxycyclohexyl)ethyl)phenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-{2-[(tert-butoxycarbonyl)(methyl)amino]-1-(1-hydroxycyclohexyl)ethyl}phenoxy)oxane-2-carboxylate
• Synonyms: rac N-Boc-N,O-Didesmethyl Venlafaxine 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 162256617
• PubChem CID: 71314137

CALCULATED PROPERTIES

• Acid pKa: 14.425701
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 3.0142505
• LogD (pH = 7.4): 3.0142505
• Log P: 3.0142505
• Molar Refractivity: 162.4777 cm^3
• Polarizability: 65.75817 Å^3
• Polar Surface Area: 173.43 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B646860

Protected Venlafaxine metabolite.