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

• ChemBase ID: 167101
• Molecular Formular: C20H19Cl2NO8
• Molecular Mass: 472.27276
• Monoisotopic Mass: 471.04877193
• SMILES: c1ccc(c(c1Cl)Nc1ccccc1CC(=O)O[C@H]1O[C@@H]([C@H](O)[C@@H](O)[C@H]1O)C(=O)O)Cl
• Canonical SMILES: O=C(Cc1ccccc1Nc1c(Cl)cccc1Cl)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C20H19Cl2NO8/c21-10-5-3-6-11(22)14(10)23-12-7-2-1-4-9(12)8-13(24)30-20-17(27)15(25)16(26)18(31-20)19(28)29/h1-7,15-18,20,23,25-27H,8H2,(H,28,29)/t15-,16-,17+,18-,20+/m1/s1
• InChIKey: JXIKYYSIYCILNG-NUABRCLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-[(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-[(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-O-[2-[(2’,6’-Dichlorophenyl)amino)]phenylacetyl]-β-D-glucopyranuronic Acid; Diclofenac Acyl-β-D-glucuronide

Database IDs

• CAS Number: 64118-81-6
• PubChem SID: 162261234
• PubChem CID: 71315976

CALCULATED PROPERTIES

• Acid pKa: 3.234132
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.0660398
• LogD (pH = 7.4): -1.1280338
• Log P: 2.3112156
• Molar Refractivity: 107.76 cm^3
• Polarizability: 42.92743 Å^3
• Polar Surface Area: 145.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 101-103°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D436475

Diclofenac-13C6 Sodium Salt13C Labelled Diclofenac Sodium Salt is a known nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor.

REFERENCES

• Kenny, J. R., et al.: J. Med. Chem., 47, 2816 (2004)