(2R)-3-phenyl-2-[(2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanamido]propanoic acid

• ChemBase ID: 176510
• Molecular Formular: C28H36N2O4
• Molecular Mass: 464.59644
• Monoisotopic Mass: 464.26750764
• SMILES: C([C@@H](NC(=O)[C@@H]1CC[C@H](CC1)C(C)C)C(=O)N[C@H](Cc1ccccc1)C(=O)O)c1ccccc1
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)N[C@@H](C(=O)N[C@@H](C(=O)O)Cc1ccccc1)Cc1ccccc1)C
• InChI: InChI=1S/C28H36N2O4/c1-19(2)22-13-15-23(16-14-22)26(31)29-24(17-20-9-5-3-6-10-20)27(32)30-25(28(33)34)18-21-11-7-4-8-12-21/h3-12,19,22-25H,13-18H2,1-2H3,(H,29,31)(H,30,32)(H,33,34)/t22-,23-,24-,25-/m1/s1
• InChIKey: XMXSUTQQSCOJBE-ZGFBMJKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-phenyl-2-[(2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanamido]propanoic acid
• IUPAC Traditional name: (2R)-3-phenyl-2-[(2R)-3-phenyl-2-{[(1r,4r)-4-isopropylcyclohexyl]formamido}propanamido]propanoic acid
• Synonyms: N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanyl-D-phenylalanine; N-[(trans-4-Isopropylcyclohexyl)carbonyl]-D-phenylalanyl-D-phenylalanine; D-Phenylalanyl Nateglinide

Database IDs

• CAS Number: 944746-48-9
• PubChem SID: 164232420
• PubChem CID: 71157707

CALCULATED PROPERTIES

• Acid pKa: 3.9009287
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.5435557
• LogD (pH = 7.4): 1.9352541
• Log P: 5.148378
• Molar Refractivity: 131.3769 cm^3
• Polarizability: 51.584686 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P319435

An impurity of the oral hypoglycemic agent Nateglinide (N379375) used in forced degradation studies.

REFERENCES

• Pathare, D.B. et al.: Drug Dev. Indust. Pharm., 33, 551 (2007)