4-({[(1S)-1-(2-aminophenyl)-3-methylbutyl]carbamoyl}methyl)-2-ethoxybenzoic acid

• ChemBase ID: 166649
• Molecular Formular: C22H28N2O4
• Molecular Mass: 384.46872
• Monoisotopic Mass: 384.20490739
• SMILES: c1cccc(c1[C@@H](NC(=O)Cc1cc(c(cc1)C(=O)O)OCC)CC(C)C)N
• Canonical SMILES: CCOc1cc(ccc1C(=O)O)CC(=O)N[C@H](c1ccccc1N)CC(C)C
• InChI: InChI=1S/C22H28N2O4/c1-4-28-20-12-15(9-10-17(20)22(26)27)13-21(25)24-19(11-14(2)3)16-7-5-6-8-18(16)23/h5-10,12,14,19H,4,11,13,23H2,1-3H3,(H,24,25)(H,26,27)/t19-/m0/s1
• InChIKey: OSCVKZCOJUTUFD-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({[(1S)-1-(2-aminophenyl)-3-methylbutyl]carbamoyl}methyl)-2-ethoxybenzoic acid
• IUPAC Traditional name: 4-({[(1S)-1-(2-aminophenyl)-3-methylbutyl]carbamoyl}methyl)-2-ethoxybenzoic acid
• Synonyms: Repaglinide M1 metabolite; 2-Despiperidyl-2-amino Repaglinide; 4-[2-[[(1S)-1-(2-Aminophenyl)-3-methylbutyl]amino]-2-oxoethyl]-2-ethoxybenzoic Acid

Database IDs

• CAS Number: 637301-29-2
• PubChem SID: 162260782
• PubChem CID: 29977666

CALCULATED PROPERTIES

• Acid pKa: 3.9216244
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6667868
• LogD (pH = 7.4): 0.1532366
• Log P: 2.8753054
• Molar Refractivity: 109.9579 cm^3
• Polarizability: 41.842384 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 66-68°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D297150

A metabolite of Repaglinide (M1).

REFERENCES

• 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)
• Balfour, J., et al.: Drugs, 61, 815 (2001)