2-ethoxy-4-({[(1R)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid

• ChemBase ID: 177394
• Molecular Formular: C27H36N2O4
• Molecular Mass: 452.58574
• Monoisotopic Mass: 452.26750764
• SMILES: c1cccc(c1[C@H](NC(=O)Cc1cc(c(cc1)C(=O)O)OCC)CC(C)C)N1CCCCC1
• Canonical SMILES: CCOc1cc(ccc1C(=O)O)CC(=O)N[C@@H](c1ccccc1N1CCCCC1)CC(C)C
• InChI: InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m1/s1
• InChIKey: FAEKWTJYAYMJKF-HSZRJFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-ethoxy-4-({[(1R)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid
• IUPAC Traditional name: 2-ethoxy-4-({[(1R)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid
• Synonyms: 2-Ethoxy-4-[2-[[(1R)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid; (-)-Repaglinide; AG-EE 624ZW; Repaglinide Impurity; (R)-(-)-Repaglinide (Repaglinide Impurity)

Database IDs

• CAS Number: 147852-26-4
• PubChem SID: 164233304
• PubChem CID: 10479034

CALCULATED PROPERTIES

• Acid pKa: 3.6754997
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.3981318
• LogD (pH = 7.4): 1.9463284
• Log P: 3.9468045
• Molar Refractivity: 131.8281 cm^3
• Polarizability: 50.317257 Å^3
• Polar Surface Area: 78.87 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R144490

The R-enantiomer showed only weak hypoglycemic activity. Repaglinide impurity.

REFERENCES

• Rufer, C., et al.: J. Med. Chem., 22, 750 (1979)
• Garrino, M., et al.: Diabetologia, 28, 697 (1979)
• Garrino, M., et al.: Br. J. Pharmacol., 93, 61 (1979)
• Panten, U., et al.: Biochem. Pharmacol., 38, 1217 (1979)
• Verspohl, E., et al.: J. Pharm. Pharmaco