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

• ChemBase ID: 175028
• Molecular Formular: C32H41NO9
• Molecular Mass: 583.66924
• Monoisotopic Mass: 583.2781319
• SMILES: C(C(NC(=O)[C@@H]1CC[C@H](CC1)C(C)C)C(=O)O[C@@H]1OC([C@H](C([C@H]1O)O)O)C(=O)OCc1ccccc1)c1ccccc1
• Canonical SMILES: CC([C@@H]1CC[C@H](CC1)C(=O)NC(C(=O)O[C@@H]1OC(C(=O)OCc2ccccc2)[C@H](C([C@H]1O)O)O)Cc1ccccc1)C
• InChI: InChI=1S/C32H41NO9/c1-19(2)22-13-15-23(16-14-22)29(37)33-24(17-20-9-5-3-6-10-20)30(38)42-32-27(36)25(34)26(35)28(41-32)31(39)40-18-21-11-7-4-8-12-21/h3-12,19,22-28,32,34-36H,13-18H2,1-2H3,(H,33,37)/t22-,23-,24?,25?,26-,27-,28?,32-/m0/s1
• InChIKey: FETBIPXTQOAEAM-YOFVAGNESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 164230938
• PubChem CID: 71750957

CALCULATED PROPERTIES

• Acid pKa: 11.896516
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 3.9511435
• LogD (pH = 7.4): 3.9511313
• Log P: 3.9511445
• Molar Refractivity: 151.1408 cm^3
• Polarizability: 60.640316 Å^3
• Polar Surface Area: 151.62 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N379390

Intermediate in the production of Nateglinide metabolites