(2S,3S,4S,5R,6S)-6-{[2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169026
• Molecular Formular: C19H20F2N6O7
• Molecular Mass: 482.3949064
• Monoisotopic Mass: 482.13615345
• SMILES: n1(CC(Cn2ncnc2)(c2ccc(cc2F)F)O[C@@H]2O[C@H]([C@H]([C@@H]([C@@H]2O)O)O)C(=O)O)cncn1
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(c2ccc(cc2F)F)(Cn2cncn2)Cn2cncn2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C19H20F2N6O7/c20-10-1-2-11(12(21)3-10)19(4-26-8-22-6-24-26,5-27-9-23-7-25-27)34-18-15(30)13(28)14(29)16(33-18)17(31)32/h1-3,6-9,13-16,18,28-30H,4-5H2,(H,31,32)/t13-,14-,15+,16-,18-/m0/s1
• InChIKey: GJQIGLSHRFZUJD-RPUYLAQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-(1H-1,2,4-triazol-1-ylmethyl)ethyl β-D-Glucopyranosiduronic Acid; Fluconazole Glucuronide; Fluconazole β-D-Glucuronide

Database IDs

• CAS Number: 136134-23-1
• PubChem SID: 162263158
• PubChem CID: 71316779

CALCULATED PROPERTIES

• Acid pKa: 3.189495
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -3.3486907
• LogD (pH = 7.4): -4.3636627
• Log P: -1.3517712
• Molar Refractivity: 129.4802 cm^3
• Polarizability: 40.745975 Å^3
• Polar Surface Area: 177.87 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F421015

Fluconazole β-D-Glucuronide is a metabolite of Fluconazole (F421000).

REFERENCES

• Brammer, K.W., et al.: Drug Metab. Dispos.,19, 764 (1991)