(2S,3S,4S,5R,6R)-6-({2-[(ethoxycarbonyl)amino]-5-{[(4-fluorophenyl)methyl]amino}phenyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177436
• Molecular Formular: C22H26FN3O8
• Molecular Mass: 479.4555432
• Monoisotopic Mass: 479.17039303
• SMILES: c1(ccc(cc1)CNc1ccc(c(c1)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)NC(=O)OCC)F
• Canonical SMILES: CCOC(=O)Nc1ccc(cc1N[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)NCc1ccc(cc1)F
• InChI: InChI=1S/C22H26FN3O8/c1-2-33-22(32)26-14-8-7-13(24-10-11-3-5-12(23)6-4-11)9-15(14)25-20-18(29)16(27)17(28)19(34-20)21(30)31/h3-9,16-20,24-25,27-29H,2,10H2,1H3,(H,26,32)(H,30,31)/t16-,17-,18+,19-,20+/m0/s1
• InChIKey: AVGRGNFEIQMATO-UHZRXMQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-({2-[(ethoxycarbonyl)amino]-5-{[(4-fluorophenyl)methyl]amino}phenyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-({2-[(ethoxycarbonyl)amino]-5-{[(4-fluorophenyl)methyl]amino}phenyl}amino)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-Deoxy-1-[[2-[(ethoxycarbonyl)amino]-5-[[(4-fluorophenyl)methyl]amino]phenyl]amino] β-D-Glucopyranuronic Acid; Retigabine N-β-D-Glucuronide

Database IDs

• CAS Number: 191873-41-3
• PubChem SID: 164233346
• PubChem CID: 71752020

CALCULATED PROPERTIES

• Acid pKa: 3.2044854
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -1.240818
• LogD (pH = 7.4): -2.50979
• Log P: -0.048746508
• Molar Refractivity: 120.0393 cm^3
• Polarizability: 44.758842 Å^3
• Polar Surface Area: 169.61 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R189060

Retigabine N-β-D-Glucuronide is the major metabolite of the antiepileptic drug Retigabine (R189050) that is produced via N-glucuronidation in humans.

REFERENCES

• Hiller, A. et al.: Drug Metab. Dispos., 27, 605 (1999)
• Borlak, J. et al.: Metab. Clin. Exp., 55, 711 (1999)
• McNeilly, P.P. et al.: Zenobiotica, 27, 431 (1999)