(2S,3S,4S,5R,6R)-6-{1-[4-chloro-3-(trifluoromethyl)phenyl][(4-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}phenyl)carbamoyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177833
• Molecular Formular: C27H24ClF3N4O9
• Molecular Mass: 640.9490696
• Monoisotopic Mass: 640.11839071
• SMILES: c1(ccc(cc1)Oc1ccnc(c1)C(=O)NC)NC(=O)N([C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)c1cc(c(cc1)Cl)C(F)(F)F
• Canonical SMILES: CNC(=O)c1nccc(c1)Oc1ccc(cc1)NC(=O)N([C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)c1ccc(c(c1)C(F)(F)F)Cl
• InChI: InChI=1S/C27H24ClF3N4O9/c1-32-23(39)18-11-15(8-9-33-18)43-14-5-2-12(3-6-14)34-26(42)35(13-4-7-17(28)16(10-13)27(29,30)31)24-21(38)19(36)20(37)22(44-24)25(40)41/h2-11,19-22,24,36-38H,1H3,(H,32,39)(H,34,42)(H,40,41)/t19-,20-,21+,22-,24+/m0/s1
• InChIKey: HALZWBPBJOJUOZ-QMDPOKHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{1-[4-chloro-3-(trifluoromethyl)phenyl][(4-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}phenyl)carbamoyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{1-[4-chloro-3-(trifluoromethyl)phenyl][(4-{[2-(methylcarbamoyl)pyridin-4-yl]oxy}phenyl)carbamoyl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[[4-Chloro-3-(trifluoromethyl)phenyl][[[4-[[2-[(methylamino)carbonyl]-4-pyridinyl]oxy]phenyl]amino]carbonyl]amino]-1-deoxy-β-D-glucopyranuronic Acid; Sorafenib β-D-GlucuronideDISCONTINUED

Database IDs

• CAS Number: 1130164-93-0
• PubChem SID: 164233743
• PubChem CID: 71752221

CALCULATED PROPERTIES

• Acid pKa: 3.4405856
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 0.04870731
• LogD (pH = 7.4): -1.2831045
• Log P: 1.9325448
• Molar Refractivity: 145.1637 cm^3
• Polarizability: 55.032158 Å^3
• Polar Surface Area: 190.78 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S676855

A glucuronide metabolite of Sorafenib (S676850).

REFERENCES

• O'Neil, B., et al.: Oncologist, 12, 1425 (2007)
• Jain, L., et al.: J. Pharm. Biomed. Anal., 46, 362 (2007)