ethyl (2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoate

• ChemBase ID: 175033
• Molecular Formular: C21H31NO3
• Molecular Mass: 345.47574
• Monoisotopic Mass: 345.23039386
• SMILES: C([C@@H](NC(=O)[C@@H]1CC[C@H](CC1)C(C)C)C(=O)OCC)c1ccccc1
• Canonical SMILES: CCOC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H]1CC[C@H](CC1)C(C)C
• InChI: InChI=1S/C21H31NO3/c1-4-25-21(24)19(14-16-8-6-5-7-9-16)22-20(23)18-12-10-17(11-13-18)15(2)3/h5-9,15,17-19H,4,10-14H2,1-3H3,(H,22,23)/t17-,18-,19-/m1/s1
• InChIKey: AVOHCDLQBWDQOF-GUDVDZBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoate
• IUPAC Traditional name: ethyl (2R)-3-phenyl-2-{[(1r,4r)-4-isopropylcyclohexyl]formamido}propanoate
• Synonyms: N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine Ethyl Ester; Nateglinide Ethyl Ester

Database IDs

• CAS Number: 187728-85-4
• PubChem SID: 164230943
• PubChem CID: 25000304

CALCULATED PROPERTIES

• Acid pKa: 12.76201
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.531272
• LogD (pH = 7.4): 4.531271
• Log P: 4.531273
• Molar Refractivity: 98.9782 cm^3
• Polarizability: 39.194775 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N379810

The ethyl ester of the oral hypoglycemic agent Nateglinide (N379375). It showed no effects on gross behavior in mice.

REFERENCES

• Maeda, K. et al.: Yak. Chir., 25, S157 (1997)