4-[(3aR,7aS)-octahydro-1H-isoindol-2-yl]-2-benzyl-4-oxobutanoic acid

• ChemBase ID: 179724
• Molecular Formular: C19H25NO3
• Molecular Mass: 315.4067
• Monoisotopic Mass: 315.18344367
• SMILES: N1(C(=O)CC(C(=O)O)Cc2ccccc2)C[C@H]2[C@@H](C1)CCCC2
• Canonical SMILES: O=C(N1C[C@@H]2[C@H](C1)CCCC2)CC(C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C19H25NO3/c21-18(20-12-15-8-4-5-9-16(15)13-20)11-17(19(22)23)10-14-6-2-1-3-7-14/h1-3,6-7,15-17H,4-5,8-13H2,(H,22,23)/t15-,16+,17?
• InChIKey: WPGGHFDDFPHPOB-SJPCQFCGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(3aR,7aS)-octahydro-1H-isoindol-2-yl]-2-benzyl-4-oxobutanoic acid
• IUPAC Traditional name: 4-[(3aR,7aS)-octahydro-1H-isoindol-2-yl]-2-benzyl-4-oxobutanoic acid
• Synonyms: Glufast; Mitiglinide

Database IDs

• CAS Number: 145324-16-9
• PubChem SID: 164235634
• PubChem CID: 10734122

CALCULATED PROPERTIES

• Acid pKa: 4.6218934
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9932944
• LogD (pH = 7.4): 0.21648112
• Log P: 2.92444
• Molar Refractivity: 88.3071 cm^3
• Polarizability: 34.530243 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Stimulates insulin secretion

Product Information

• Application(s): Oral hypoglycaemic agent for the treatment of type 2 diabetes

REFERENCES

• Eur. Pat., 1992, Kissei, 507 534; CA, 118, 59584b, (synth, isomers, pharmacol)
• Mogami, H. et al., Eur. J. Pharmacol., 1994, 269, 293-298, (pharmacol)
• Malaisse, W.J., Horm. Metab. Res., 1995, 27, 263-266, (pharmacol)
• Lins, L. et al., Biochem. Pharmacol., 1996, 52, 1155-1168, (pmr, cmr, pharmacol)
• Kinukawa, M. et al., Br. J. Pharmacol., 1996, 117, 1702-1706, (pharmacol)
• Ulusoy, S. et al., Diabetes Res., 1996, 31, 27-31, (pharmacol)
• Sunaga, Y. et al., Eur. J. Pharmacol., 2001, 431, 119-125, (pharmacol)