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

• ChemBase ID: 166618
• Molecular Formular: C29H41NO11
• Molecular Mass: 579.63594
• Monoisotopic Mass: 579.26796114
• SMILES: c1cc(ccc1C(C1(CCCCC1)O)CN(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)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C29H41NO11/c1-17(31)37-23-24(38-18(2)32)26(39-19(3)33)28(41-25(23)27(34)36-6)40-21-12-10-20(11-13-21)22(16-30(4)5)29(35)14-8-7-9-15-29/h10-13,22-26,28,35H,7-9,14-16H2,1-6H3/t22?,23-,24-,25-,26+,28+/m0/s1
• InChIKey: HLOVYAMOGATVJD-BNAKVLINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[2-(dimethylamino)-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-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenoxy}oxane-2-carboxylate
• Synonyms: 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester; 4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenyl2,3,4-Tri-O-acetyl-β-D-glucuronic Acid Methyl Ester; rac O-Desmethyl Venlafaxine 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 162260751
• PubChem CID: 71315802

CALCULATED PROPERTIES

• Acid pKa: 14.416948
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.0308973
• LogD (pH = 7.4): 0.6081284
• Log P: 2.1141055
• Molar Refractivity: 142.7773 cm^3
• Polarizability: 57.87626 Å^3
• Polar Surface Area: 147.13 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid (Foam)

DETAILS

Toronto Research Chemicals - D296535

Venlafaxine metabolite intermediate