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

• ChemBase ID: 167234
• Molecular Formular: C27H37NO11
• Molecular Mass: 551.58278
• Monoisotopic Mass: 551.23666101
• SMILES: c1cc(ccc1C(C1(CCCCC1)O)CN)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@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C27H37NO11/c1-15(29)35-21-22(36-16(2)30)24(37-17(3)31)26(39-23(21)25(32)34-4)38-19-10-8-18(9-11-19)20(14-28)27(33)12-6-5-7-13-27/h8-11,20-24,26,33H,5-7,12-14,28H2,1-4H3/t20?,21-,22-,23-,24+,26+/m0/s1
• InChIKey: MSNVVCQTMAJWRD-APEDDKMTSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162261367
• PubChem CID: 71316025

CALCULATED PROPERTIES

• Acid pKa: 14.417602
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.6824026
• LogD (pH = 7.4): -0.69092023
• Log P: 1.298477
• Molar Refractivity: 132.708 cm^3
• Polarizability: 54.221745 Å^3
• Polar Surface Area: 169.91 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D440985

Intermediate for the synthesis of N,N-Didesmethyl-O-desmethyl rac-Venlafaxine Glucuronide.