(2R,3R,4R,5S,6R)-6-[(2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172432
• Molecular Formular: C21H21ClFNO8
• Molecular Mass: 469.8447432
• Monoisotopic Mass: 469.09397254
• SMILES: c1(ccc(c(c1)CC(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)Nc1c(cccc1F)Cl)C
• Canonical SMILES: O=C(Cc1cc(C)ccc1Nc1c(F)cccc1Cl)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C21H21ClFNO8/c1-9-5-6-13(24-15-11(22)3-2-4-12(15)23)10(7-9)8-14(25)31-21-18(28)16(26)17(27)19(32-21)20(29)30/h2-7,16-19,21,24,26-28H,8H2,1H3,(H,29,30)/t16-,17-,18+,19-,21+/m1/s1
• InChIKey: GEVZOJTWMGGTTK-YRIDSSQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-[(2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-[(2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[2-[(2-Chloro-6-fluorophenyl)amino]-5-methylbenzeneacetate] β-D-Glucopyranuronic Acid; Lumiracoxib Acyl-β-D-glucuronide

Database IDs

• CAS Number: 697287-17-5
• PubChem SID: 164228342
• PubChem CID: 71749854

CALCULATED PROPERTIES

• Acid pKa: 3.2442968
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.12770517
• LogD (pH = 7.4): -1.0740309
• Log P: 2.3632944
• Molar Refractivity: 108.2128 cm^3
• Polarizability: 42.510113 Å^3
• Polar Surface Area: 145.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L474710

A metabolite of Lumiracoxib.

REFERENCES

• Fu, J., et al.: J. Biol. Chem., 265, 16737 (1990)
• Goldstein, J., et al.: Am. J. Gastroenterol., 96, 1019 (1990)
• Flower, R., et al.: Nat. Rev. Drug Discov., 2, 179 (1990)
• Grillo, M., et al.: Drug Metab. Dispos., 31, 1327 (1990)