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

• ChemBase ID: 175624
• Molecular Formular: C22H24F3NO7
• Molecular Mass: 471.4236696
• Monoisotopic Mass: 471.15048677
• SMILES: C(CCN[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)(Oc1ccc(cc1)C(F)(F)F)c1ccccc1
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](NCCC(c2ccccc2)Oc2ccc(cc2)C(F)(F)F)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H24F3NO7/c23-22(24,25)13-6-8-14(9-7-13)32-15(12-4-2-1-3-5-12)10-11-26-20-18(29)16(27)17(28)19(33-20)21(30)31/h1-9,15-20,26-29H,10-11H2,(H,30,31)/t15?,16-,17-,18+,19-,20+/m0/s1
• InChIKey: GXZQMXPRYAFVRG-OJRVOLPLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 96735-72-7
• PubChem SID: 164231534
• PubChem CID: 71751199

CALCULATED PROPERTIES

• Acid pKa: 2.990476
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.39264107
• LogD (pH = 7.4): -0.59018075
• Log P: -0.39270756
• Molar Refractivity: 107.897 cm^3
• Polarizability: 42.300926 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N681110

A glucuronide of Norfluoxetine (N681100) metabolite in humans.

REFERENCES

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