sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amino]oxane-2-carboxylate

• ChemBase ID: 169205
• Molecular Formular: C23H25F3NNaO7
• Molecular Mass: 507.4320796
• Monoisotopic Mass: 507.14808109
• SMILES: C(CCN([C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])C)(Oc1ccc(cc1)C(F)(F)F)c1ccccc1.[Na+]
• Canonical SMILES: CN([C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)CCC(c1ccccc1)Oc1ccc(cc1)C(F)(F)F.[Na+]
• InChI: InChI=1S/C23H26F3NO7.Na/c1-27(21-19(30)17(28)18(29)20(34-21)22(31)32)12-11-16(13-5-3-2-4-6-13)33-15-9-7-14(8-10-15)23(24,25)26;/h2-10,16-21,28-30H,11-12H2,1H3,(H,31,32);/q;+1/p-1/t16?,17-,18-,19+,20-,21+;/m0./s1
• InChIKey: RRKRXIFOHFBLHY-YEZSYGFXSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amino]oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[methyl({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl})amino]oxane-2-carboxylate
• Synonyms: 1-Deoxy-1-[methyl[3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]amino]-β-D-glucopyranuronic Acid; Fluoxetine N-β-D-Glucuronide Sodium Salt

Database IDs

• PubChem SID: 162263337
• PubChem CID: 71316863

CALCULATED PROPERTIES

• Acid pKa: 3.3675983
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.100094624
• LogD (pH = 7.4): -0.82984674
• Log P: -0.0689478
• Molar Refractivity: 124.0288 cm^3
• Polarizability: 43.998035 Å^3
• Polar Surface Area: 122.52 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F597105

A glucuronide metabolite of Fluoxetine (F597100) in humans.

REFERENCES

• Lemberger, L., et al.: J. Clin. Psychiatry, 46, 14 (1985)