(2S,3S,4S,5R,6R)-6-{[(5E)-5-[(2-aminoethoxy)imino]-5-[4-(trifluoromethyl)phenyl]pentyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 166439
• Molecular Formular: C20H27F3N2O8
• Molecular Mass: 480.4321896
• Monoisotopic Mass: 480.17195049
• SMILES: c1cc(ccc1/C(=N/OCCN)/CCCCO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C(F)(F)F
• Canonical SMILES: NCCO/N=C(/c1ccc(cc1)C(F)(F)F)\CCCCO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H27F3N2O8/c21-20(22,23)12-6-4-11(5-7-12)13(25-32-10-8-24)3-1-2-9-31-19-16(28)14(26)15(27)17(33-19)18(29)30/h4-7,14-17,19,26-28H,1-3,8-10,24H2,(H,29,30)/b25-13+/t14-,15-,16+,17-,19+/m0/s1
• InChIKey: BFHCANBAKJDDQR-PCTIKJEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(5E)-5-[(2-aminoethoxy)imino]-5-[4-(trifluoromethyl)phenyl]pentyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(5E)-5-[(2-aminoethoxy)imino]-5-[4-(trifluoromethyl)phenyl]pentyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (E)-5-[(2-Aminoethoxy)imino]-5-[4-(trifluoromethyl)phenyl]pentyl β-D-Glucopyranosiduronic Acid; Desmethyl Fluvoxamine β-D-Glucuronide

Database IDs

• CAS Number: 89103-66-2
• PubChem SID: 162260572
• PubChem CID: 71315737

CALCULATED PROPERTIES

• Acid pKa: 3.2760706
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.563093
• LogD (pH = 7.4): -1.5679104
• Log P: -1.5618157
• Molar Refractivity: 106.7266 cm^3
• Polarizability: 41.68481 Å^3
• Polar Surface Area: 164.06 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D291633

A metabolite of Fluvoxamine (F603500).

REFERENCES

• Ruijten, H.M., et al.: Drug Metab. Dispos., 12, 82 (1984)