(2R)-3-phenyl-2-{[(1s,4r)-4-ethylcyclohexyl]formamido}propanoic acid

• ChemBase ID: 166333
• Molecular Formular: C18H25NO3
• Molecular Mass: 303.396
• Monoisotopic Mass: 303.18344367
• SMILES: C([C@@H](NC(=O)[C@@H]1CC[C@H](CC1)CC)C(=O)O)c1ccccc1
• Canonical SMILES: CC[C@@H]1CC[C@H](CC1)C(=O)N[C@@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C18H25NO3/c1-2-13-8-10-15(11-9-13)17(20)19-16(18(21)22)12-14-6-4-3-5-7-14/h3-7,13,15-16H,2,8-12H2,1H3,(H,19,20)(H,21,22)/t13-,15-,16-/m1/s1
• InChIKey: LLSFDDAYCLFQJP-FVQBIDKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-phenyl-2-{[(1s,4r)-4-ethylcyclohexyl]formamido}propanoic acid
• IUPAC Traditional name: (2R)-3-phenyl-2-{[(1s,4r)-4-ethylcyclohexyl]formamido}propanoic acid
• Synonyms: trans-N-[(4-Ethylcyclohexyl)carbonyl]-D-phenylalanine; 4-Desisopropyl-4-ethyl Nateglinide

Database IDs

• CAS Number: 105746-45-0
• PubChem SID: 162260466
• PubChem CID: 14233118

CALCULATED PROPERTIES

• Acid pKa: 4.105905
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.333425
• LogD (pH = 7.4): 0.6463225
• Log P: 3.7415516
• Molar Refractivity: 84.9119 cm^3
• Polarizability: 33.416107 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D290235

D-phenylanaline derivative and an analog Nateglinide (N379375) with similar hypoglycemic activity.

REFERENCES

• Shinkai, H. et al.: J. Med. Chem., 32, 1436 (1989)