4-{[(1-{2-[(4-carboxybutyl)amino]phenyl}-3-methylbutyl)carbamoyl]methyl}-2-ethoxybenzoic acid

• ChemBase ID: 166651
• Molecular Formular: C27H36N2O6
• Molecular Mass: 484.58454
• Monoisotopic Mass: 484.25733688
• SMILES: c1cccc(c1C(NC(=O)Cc1cc(c(cc1)C(=O)O)OCC)CC(C)C)NCCCCC(=O)O
• Canonical SMILES: CCOc1cc(ccc1C(=O)O)CC(=O)NC(c1ccccc1NCCCCC(=O)O)CC(C)C
• InChI: InChI=1S/C27H36N2O6/c1-4-35-24-16-19(12-13-21(24)27(33)34)17-25(30)29-23(15-18(2)3)20-9-5-6-10-22(20)28-14-8-7-11-26(31)32/h5-6,9-10,12-13,16,18,23,28H,4,7-8,11,14-15,17H2,1-3H3,(H,29,30)(H,31,32)(H,33,34)
• InChIKey: ZOMBGPVQRXZSGW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1-{2-[(4-carboxybutyl)amino]phenyl}-3-methylbutyl)carbamoyl]methyl}-2-ethoxybenzoic acid
• IUPAC Traditional name: 4-{[(1-{2-[(4-carboxybutyl)amino]phenyl}-3-methylbutyl)carbamoyl]methyl}-2-ethoxybenzoic acid
• Synonyms: 4-[2-[[1-[2-[(4-Carboxybutyl)amino]phenyl]-3-methylbutyl]amino]-2-oxoethyl]-2-ethoxybenzoic Acid; Repaglinide M2 metabolite; 2-Despiperidyl-2-(5-carboxypentylamine) Repaglinide

Database IDs

• CAS Number: 874908-12-0
• PubChem SID: 162260784
• PubChem CID: 46781210

CALCULATED PROPERTIES

• Acid pKa: 3.538518
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.3874791
• LogD (pH = 7.4): -1.8922998
• Log P: 3.264421
• Molar Refractivity: 135.5913 cm^3
• Polarizability: 51.579506 Å^3
• Polar Surface Area: 124.96 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 45-52°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D297170

A metabolite of Repaglinide (M2).

REFERENCES

• Balfour, J., et al.: Drugs, 61, 815 (2001)
• Backman, J., et al.: Clin. Pharmacol. Ther., 72, 685 (2001)
• Hatorp, V., et al.: Clin. Pharmacokinet., 41, 471 (2001)
• Niemi, M., et al.: Diabetologia, 46, 347 (2001)