(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoyl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 175026
• Molecular Formular: C25H35NO9
• Molecular Mass: 493.5467
• Monoisotopic Mass: 493.23118171
• SMILES: C([C@@H](NC(=O)[C@@H]1CC[C@H](CC1)C(C)C)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)c1ccccc1
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)N[C@@H](C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)Cc1ccccc1)C
• InChI: InChI=1S/C25H35NO9/c1-13(2)15-8-10-16(11-9-15)22(30)26-17(12-14-6-4-3-5-7-14)24(33)35-25-20(29)18(27)19(28)21(34-25)23(31)32/h3-7,13,15-21,25,27-29H,8-12H2,1-2H3,(H,26,30)(H,31,32)/t15-,16-,17-,18+,19+,20-,21+,25+/m1/s1
• InChIKey: YTIRWNSTJVSCRW-BBFBHBGISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R)-3-phenyl-2-{[(1r,4r)-4-(propan-2-yl)cyclohexyl]formamido}propanoyl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R)-3-phenyl-2-{[(1r,4r)-4-isopropylcyclohexyl]formamido}propanoyl]oxy}oxane-2-carboxylic acid
• Synonyms: N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine β-D-Glucopyranuronic Acid; Nateglinide Acyl Glucuronide; Nateglinide Acyl-β-D-glucuronide

Database IDs

• CAS Number: 183996-85-2
• PubChem SID: 164230936
• PubChem CID: 71750955

CALCULATED PROPERTIES

• Acid pKa: 3.171759
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.2231105
• LogD (pH = 7.4): -1.3695333
• Log P: 2.0807772
• Molar Refractivity: 121.7591 cm^3
• Polarizability: 49.041466 Å^3
• Polar Surface Area: 162.62 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 105-107°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N379380

A metabolite of Nateglinide (N379375), a novel D-phenylalanine-derivative hypoglycemic agent

REFERENCES

• Korzekwa, K., et al.: Drug Metab. Dispos., 18, 974 (1990)
• Takesada, H., et al.: Bioorg. Med. Chem., 4, 1771 (1990)
• Ikenoue, T., et al.: Br. J. Pharmacol., 120, 137 (1990)
• Karara, A., et al.: J. Clin. Pharmacol., 39, 172 (1990)
• Hanefeld, M., et al.: Di