(2S,3S,4S,5R,6S)-6-{3-[(3R,4R)-1-[(2S)-2-benzyl-2-[(carboxymethyl)carbamoyl]ethyl]-3,4-dimethylpiperidin-4-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 159750
• 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)Cc1ccccc1)(c1cc(ccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)C)C
• Canonical SMILES: OC(=O)CNC(=O)[C@@H](Cc1ccccc1)CN1CC[C@@]([C@H](C1)C)(C)c1cccc(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C31H40N2O10/c1-18-16-33(17-20(28(39)32-15-23(34)35)13-19-7-4-3-5-8-19)12-11-31(18,2)21-9-6-10-22(14-21)42-30-26(38)24(36)25(37)27(43-30)29(40)41/h3-10,14,18,20,24-27,30,36-38H,11-13,15-17H2,1-2H3,(H,32,39)(H,34,35)(H,40,41)/t18-,20-,24-,25-,26+,27-,30+,31+/m0/s1
• InChIKey: JBCMMCUAUBTEKI-IGJSLWCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{3-[(3R,4R)-1-[(2S)-2-benzyl-2-[(carboxymethyl)carbamoyl]ethyl]-3,4-dimethylpiperidin-4-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{3-[(3R,4R)-1-[(2S)-2-benzyl-2-(carboxymethylcarbamoyl)ethyl]-3,4-dimethylpiperidin-4-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Alvimopan β-D-Glucuronide

Database IDs

• PubChem SID: 162253885
• PubChem CID: 71313122

CALCULATED PROPERTIES

• Acid pKa: 2.848873
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.852112
• LogD (pH = 7.4): -4.399391
• Log P: -1.3484894
• Molar Refractivity: 152.5711 cm^3
• Polarizability: 60.483837 Å^3
• Polar Surface Area: 186.09 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A575790

A glucuronide metabolite of Alvimopan (A575800).