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

• ChemBase ID: 167838
• Molecular Formular: C27H36N2O6
• Molecular Mass: 484.58454
• Monoisotopic Mass: 484.25733688
• SMILES: c1cccc(c1C(NC(=O)Cc1cc(c(cc1)C(=O)O)OCC)CC(O)(C)C)N1CC(CCC1)O
• Canonical SMILES: CCOc1cc(ccc1C(=O)O)CC(=O)NC(c1ccccc1N1CCCC(C1)O)CC(O)(C)C
• InChI: InChI=1S/C27H36N2O6/c1-4-35-24-14-18(11-12-21(24)26(32)33)15-25(31)28-22(16-27(2,3)34)20-9-5-6-10-23(20)29-13-7-8-19(30)17-29/h5-6,9-12,14,19,22,30,34H,4,7-8,13,15-17H2,1-3H3,(H,28,31)(H,32,33)
• InChIKey: BNUWWPKVNAJZHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-ethoxy-4-[({3-hydroxy-1-[2-(3-hydroxypiperidin-1-yl)phenyl]-3-methylbutyl}carbamoyl)methyl]benzoic acid
• IUPAC Traditional name: 2-ethoxy-4-[({3-hydroxy-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-hydroxymethylbutyl]amino]-2-oxoethyl]benzoic Acid; 3',3''-Dihydroxy Repaglinide

Database IDs

• PubChem SID: 162261971
• PubChem CID: 57347719

CALCULATED PROPERTIES

• Acid pKa: 3.7567894
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.83027035
• LogD (pH = 7.4): -0.6818024
• Log P: 2.3454163
• Molar Refractivity: 134.9821 cm^3
• Polarizability: 51.57851 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D453335

A labelled metabolite of Repaglinide (R144500).