3-phenyl-2-{[(1r,4r)-4-tert-butylcyclohexyl]formamido}propanoic acid

• ChemBase ID: 163293
• Molecular Formular: C20H29NO3
• Molecular Mass: 331.44916
• Monoisotopic Mass: 331.21474379
• SMILES: C1[C@H](CC[C@@H](C1)C(=O)NC(Cc1ccccc1)C(=O)O)C(C)(C)C
• Canonical SMILES: O=C([C@@H]1CC[C@H](CC1)C(C)(C)C)NC(C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C20H29NO3/c1-20(2,3)16-11-9-15(10-12-16)18(22)21-17(19(23)24)13-14-7-5-4-6-8-14/h4-8,15-17H,9-13H2,1-3H3,(H,21,22)(H,23,24)/t15-,16-,17?
• InChIKey: SYWRPZFKQKXPIE-BDWYFLKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-phenyl-2-{[(1r,4r)-4-tert-butylcyclohexyl]formamido}propanoic acid
• IUPAC Traditional name: 3-phenyl-2-{[(1r,4r)-4-tert-butylcyclohexyl]formamido}propanoic acid
• Synonyms: trans-N-[[4-(1,1-Dimethylethyl)cyclohexyl]carbonyl]-D-phenylalanine; N-(trans-4-tert-Butyl-cyclohexyl)carbonyl-D-phenylalanine

Database IDs

• CAS Number: 105746-46-1
• PubChem SID: 162257428
• PubChem CID: 14233115

CALCULATED PROPERTIES

• Acid pKa: 3.898222
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.721179
• LogD (pH = 7.4): 1.1140935
• Log P: 4.328618
• Molar Refractivity: 93.9356 cm^3
• Polarizability: 37.09784 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B690720

Used as an oral hypoglycemic agent. An analogue of N-(Cyclohexylcarbonyl)-D-phenylalanine.

REFERENCES

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