benzyl (3S,6S)-6-[2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 177397
• Molecular Formular: C40H50N2O10
• Molecular Mass: 718.8324
• Monoisotopic Mass: 718.34654581
• SMILES: c1cccc(c1[C@@H](NC(=O)Cc1cc(c(cc1)C(=O)O[C@H]1C(C([C@@H](C(O1)C(=O)OCc1ccccc1)O)O)O)OCC)CC(C)C)N1CCCCC1
• Canonical SMILES: CCOc1cc(ccc1C(=O)O[C@@H]1OC(C(=O)OCc2ccccc2)[C@H](C(C1O)O)O)CC(=O)N[C@H](c1ccccc1N1CCCCC1)CC(C)C
• InChI: InChI=1S/C40H50N2O10/c1-4-49-32-22-27(23-33(43)41-30(21-25(2)3)28-15-9-10-16-31(28)42-19-11-6-12-20-42)17-18-29(32)38(47)52-40-36(46)34(44)35(45)37(51-40)39(48)50-24-26-13-7-5-8-14-26/h5,7-10,13-18,22,25,30,34-37,40,44-46H,4,6,11-12,19-21,23-24H2,1-3H3,(H,41,43)/t30-,34?,35-,36?,37?,40-/m0/s1
• InChIKey: HKZJBYMHOIKRAC-ZWSVHJRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (3S,6S)-6-[2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: benzyl (3S,6S)-6-[2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: Repaglinide Acyl-β-D-glucuronide Benzyl Ester

Database IDs

• PubChem SID: 164233307
• PubChem CID: 71751996

CALCULATED PROPERTIES

• Acid pKa: 12.161173
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 5.2844024
• LogD (pH = 7.4): 5.3595343
• Log P: 5.360589
• Molar Refractivity: 193.5084 cm^3
• Polarizability: 75.68544 Å^3
• Polar Surface Area: 164.09 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid

DETAILS

Toronto Research Chemicals - R144520

Intermediate in the preparation of Repaglinide metabolites