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

• ChemBase ID: 164868
• Molecular Formular: C23H28ClNO7
• Molecular Mass: 465.92392
• Monoisotopic Mass: 465.15542992
• SMILES: c1(ccccc1C(O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)(CCN(C)C)c1ccccc1)Cl
• Canonical SMILES: CN(CCC(c1ccccc1Cl)(c1ccccc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C23H28ClNO7/c1-25(2)13-12-23(14-8-4-3-5-9-14,15-10-6-7-11-16(15)24)32-22-19(28)17(26)18(27)20(31-22)21(29)30/h3-11,17-20,22,26-28H,12-13H2,1-2H3,(H,29,30)/t17-,18-,19+,20-,22-,23?/m0/s1
• InChIKey: OMHMHPGOIYNCEV-FXACLYGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[1-(2-chlorophenyl)-3-(dimethylamino)-1-phenylpropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[1-(2-chlorophenyl)-3-(dimethylamino)-1-phenylpropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-(2-Chlorophenyl)-3-(dimethylamino)-1-phenylpropyl β-D-Glucopyranosiduronic Acid; Clophedianol O-β-D-Glucuronide; Clofedanol O-β-D-Glucuronide

Database IDs

• CAS Number: 66171-85-5
• PubChem SID: 162259002
• PubChem CID: 71314926

CALCULATED PROPERTIES

• Acid pKa: 3.2945917
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.7255954
• LogD (pH = 7.4): -0.72942466
• Log P: -0.724234
• Molar Refractivity: 117.2173 cm^3
• Polarizability: 46.675583 Å^3
• Polar Surface Area: 119.69 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C586925

A metabolite of the cough suppressant Clofedanol.

REFERENCES

• Eckhardt, G. et al.: J. Clin. Chem. Clin. Biochem., 15, 687 (1977)