(2R,3R,4R,5S,6R)-6-({2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 159749
• Molecular Formular: C31H40N2O10
• Molecular Mass: 600.6567
• Monoisotopic Mass: 600.26829549
• SMILES: [C@H]1([C@@](CCN(C1)C[C@@H](C(=O)NCC(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)Cc1ccccc1)(c1cc(ccc1)O)C)C
• Canonical SMILES: O=C(O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)CNC(=O)[C@@H](Cc1ccccc1)CN1CC[C@@]([C@H](C1)C)(C)c1cccc(c1)O
• InChI: InChI=1S/C31H40N2O10/c1-18-16-33(12-11-31(18,2)21-9-6-10-22(34)14-21)17-20(13-19-7-4-3-5-8-19)28(39)32-15-23(35)42-30-26(38)24(36)25(37)27(43-30)29(40)41/h3-10,14,18,20,24-27,30,34,36-38H,11-13,15-17H2,1-2H3,(H,32,39)(H,40,41)/t18-,20-,24+,25+,26-,27+,30-,31+/m0/s1
• InChIKey: CXXURJOYZYSQEO-JQGMIYLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-({2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-({2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Alvimopan Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 162253884
• PubChem CID: 71313121

CALCULATED PROPERTIES

• Acid pKa: 2.807627
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -1.1255175
• LogD (pH = 7.4): -1.1266469
• Log P: -1.1250687
• Molar Refractivity: 152.8579 cm^3
• Polarizability: 60.66052 Å^3
• Polar Surface Area: 186.09 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A575785

A glucuronide metabolite of Alvimopan (A575800).