(2S,3S,4S,5R,6R)-6-[(1S)-2-(carbamoyloxy)-1-(2-chlorophenyl)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 163816
• Molecular Formular: C15H18ClNO9
• Molecular Mass: 391.75772
• Monoisotopic Mass: 391.06700884
• SMILES: c1(ccccc1Cl)[C@H](O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)COC(=O)N
• Canonical SMILES: NC(=O)OC[C@H](c1ccccc1Cl)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H18ClNO9/c16-7-4-2-1-3-6(7)8(5-24-15(17)23)25-14-11(20)9(18)10(19)12(26-14)13(21)22/h1-4,8-12,14,18-20H,5H2,(H2,17,23)(H,21,22)/t8-,9+,10+,11-,12+,14-/m1/s1
• InChIKey: RKWAMNXFHLRQGF-CBIHJVFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(1S)-2-(carbamoyloxy)-1-(2-chlorophenyl)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(1S)-2-(carbamoyloxy)-1-(2-chlorophenyl)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (1S)-2-[(Aminocarbonyl)oxy]-1-(2-chlorophenyl)ethyl β-D-Glucopyranosiduronic Acid; (S)-Carisbamate β-D-O-Glucuronide

Database IDs

• CAS Number: 940279-82-3
• PubChem SID: 162257951
• PubChem CID: 71314564

CALCULATED PROPERTIES

• Acid pKa: 3.314583
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.3323827
• LogD (pH = 7.4): -3.586353
• Log P: -0.16337545
• Molar Refractivity: 83.7501 cm^3
• Polarizability: 34.11411 Å^3
• Polar Surface Area: 168.77 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C183520

A metabolite of (S)-Carisbamate (C183510).

REFERENCES

• Merrill, J., et al.: J. Lipid Res., 37, 98 (1996)
• Humerickhouse, R., et al.: Cancer Res., 60, 1189 (1996)
• Mannens, G., et al.: Drug Metab. Dispos., 35, 554 (1996)