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

• ChemBase ID: 172032
• Molecular Formular: C19H27NO4
• Molecular Mass: 333.42198
• Monoisotopic Mass: 333.19400835
• SMILES: C1CCC[C@@H]2[C@H]1CN(C2)C(=O)C[C@H](Cc1ccccc1)C(=O)O.O
• Canonical SMILES: O=C(N1C[C@@H]2[C@H](C1)CCCC2)C[C@@H](C(=O)O)Cc1ccccc1.O
• InChI: InChI=1S/C19H25NO3.H2O/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);1H2/t15-,16+,17-;/m0./s1
• InChIKey: YBMPTCIINXDDNF-VNMUXGFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-[(3aR,7aS)-octahydro-1H-isoindol-2-yl]-2-benzyl-4-oxobutanoic acid hydrate
• IUPAC Traditional name: mitiglinide hydrate
• Synonyms: (S)-2-Benzyl-4-oxo-4-(cis-perhydroisoindol-2-yl)butyric Acid Calcium Salt Hydrate; Mitiglinide Calcium Hydrate; KAD-1229 Calcium Hydrate

Database IDs

• CAS Number: 207844-01-7
• PubChem SID: 164227942
• PubChem CID: 67758547

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

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 198-200°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - K090000

KAD-1229 binds to sulfonylurea receptors and inhibits the activity of ATP-sensitive K+ channel in MIN 6 cells. Antidiabetic.

REFERENCES

• Jackson, J., et al.: Drugs, 22, 211 (1981)
• Mogami, H., et al.: Eur. J. Pharmacol., 15, 269, (1981)
• Malaisse, W., et al.: Pharmacol. Res. 32, 111 (1981)
• Ulusoy, S., et al.: Diabetes Res., 31, 27 (1981)
• Louchami, K., et al.: Pharmacol. Res., 40, 297 (19