2-ethoxy-4-[({1-[2-(3-hydroxypiperidin-1-yl)phenyl]-3-methylbutyl}carbamoyl)methyl]benzoic acid

• ChemBase ID: 171179
• Molecular Formular: C27H36N2O5
• Molecular Mass: 468.58514
• Monoisotopic Mass: 468.26242226
• SMILES: c1cccc(c1C(NC(=O)Cc1cc(c(cc1)C(=O)O)OCC)CC(C)C)N1CC(CCC1)O
• Canonical SMILES: CCOc1cc(ccc1C(=O)O)CC(=O)NC(c1ccccc1N1CCCC(C1)O)CC(C)C
• InChI: InChI=1S/C27H36N2O5/c1-4-34-25-15-19(11-12-22(25)27(32)33)16-26(31)28-23(14-18(2)3)21-9-5-6-10-24(21)29-13-7-8-20(30)17-29/h5-6,9-12,15,18,20,23,30H,4,7-8,13-14,16-17H2,1-3H3,(H,28,31)(H,32,33)
• InChIKey: OBMAZJVHPAVADF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-ethoxy-4-[({1-[2-(3-hydroxypiperidin-1-yl)phenyl]-3-methylbutyl}carbamoyl)methyl]benzoic acid
• IUPAC Traditional name: 2-ethoxy-4-[({1-[2-(3-hydroxypiperidin-1-yl)phenyl]-3-methylbutyl}carbamoyl)methyl]benzoic acid
• Synonyms: 2-Ethoxy-4-[2-[[1-[2-(3-hydroxy-1-piperidinyl)phenyl]-3-methylbutyl]amino]-2-oxoethyl]benzoic Acid; 3'-Hydroxy Repaglinide(Mixture of Diastereomers)

Database IDs

• CAS Number: 874908-14-2
• PubChem SID: 164227089
• PubChem CID: 46781896

CALCULATED PROPERTIES

• Acid pKa: 3.7569447
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.3741772
• LogD (pH = 7.4): 0.8621067
• Log P: 3.8887634
• Molar Refractivity: 133.1896 cm^3
• Polarizability: 50.943054 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 79-82°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H953280

A metabolite of Repaglinide (R144500).

REFERENCES

• Jarvis, B., et al.: Drugs, 59, 891 (2000)
• Niemi, M., et al.: Clin. Pharmacol. Ther., 70, 58 (2000)
• Hatorp, V., et al.: Clin. Pharmacokinet., 41, 471 (2000)
• Walsky, R., et al.: Drug Metab. Dispos., 33, 413 (2000)