(2R)-3-(2H5)phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid

• ChemBase ID: 175025
• Molecular Formular: C19H27NO3
• Molecular Mass: 317.42258
• Monoisotopic Mass: 317.19909373
• SMILES: C([C@@H](NC(=O)[C@@H]1CC[C@H](CC1)C(C)C)C(=O)O)c1ccccc1
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)N[C@@H](C(=O)O)Cc1ccccc1)C
• InChI: InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1
• InChIKey: OELFLUMRDSZNSF-BRWVUGGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-(^2H₅)phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoic acid
• IUPAC Traditional name: (2R)-3-(^2H₅)phenyl-2-{[(1r,4r)-4-isopropylcyclohexyl]formamido}propanoic acid
• Synonyms: N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine-d5; A 4166; AY 4166-d5; D-Nateglinide-d5; DJN 608-d5; Fastic-d5; Glinate-d5; Natelide-d5; SDZ-DJN 608-d5; Senaglinide-d5; Starlix-d5; Starlix DS-d5; Starsis-d5; Nateglinide-d5

Database IDs

• PubChem SID: 164230935
• PubChem CID: 45359040

CALCULATED PROPERTIES

• Acid pKa: 3.9972527
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.5164278
• LogD (pH = 7.4): 0.86791366
• Log P: 4.0285707
• Molar Refractivity: 89.4605 cm^3
• Polarizability: 35.278538 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 128-129°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N379377

A labelled version of Nateglinide, an amino-acid derivative that stimulates insulin secretion which is used as an antidiabetic.

REFERENCES

• Shinkai, H., et al.: J. Med. Chem., 32, 1436 (1989)
• Sato, Y., et al.: Diabetes Res. Clin. Pract., 12, 53 (1989)
• Vicent, D., et al.: J. Clin. Invest., 111, 1373 (1989)
• Ceriello, A., et al.: Diabet. Med., 21, 171 (1989)