(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({4-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-yl}oxy)oxane-2-carboxylic acid

• ChemBase ID: 170424
• Molecular Formular: C24H27NO8S
• Molecular Mass: 489.53808
• Monoisotopic Mass: 489.14573783
• SMILES: c1cc(c2c(c1O[C@H](c1cccs1)CCNC)cccc2)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CNCC[C@@H](c1cccs1)Oc1ccc(c2c1cccc2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H27NO8S/c1-25-11-10-17(18-7-4-12-34-18)31-15-8-9-16(14-6-3-2-5-13(14)15)32-24-21(28)19(26)20(27)22(33-24)23(29)30/h2-9,12,17,19-22,24-28H,10-11H2,1H3,(H,29,30)/t17-,19-,20-,21+,22-,24+/m0/s1
• InChIKey: OBIZFSZXDHWUJZ-ANUWOGMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({4-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-yl}oxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({4-[(1S)-3-(methylamino)-1-(thiophen-2-yl)propoxy]naphthalen-1-yl}oxy)oxane-2-carboxylic acid
• Synonyms: 4-[(1S)-3-(Methylamino)-1-(2-thienyl)propoxy]-1-naphthalenyl β-D-Glucopyranosiduronic Acid; LY 550408; 4-Hydroxy Duloxetine β-D-Glucuronide

Database IDs

• CAS Number: 741693-83-4
• PubChem SID: 164226334
• PubChem CID: 29981513

CALCULATED PROPERTIES

• Acid pKa: 3.0345333
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.5263485
• LogD (pH = 7.4): -0.52708244
• Log P: -0.52556026
• Molar Refractivity: 121.7266 cm^3
• Polarizability: 49.762432 Å^3
• Polar Surface Area: 137.71 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Tan to Brown Solid
• Melting Point: 182-184°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H941805

A metabolite of Duloxetine.

REFERENCES

• Lantz, R.J., et al.: Drug Dispos. Metab., 31, 1142 (2003)
• Detke, M., et al.: J. Clin Psy., 63, 308 (2003)
• Bymaster, F.P., et al.: Bioorg. Med., Chem. Lett., 13, 4477 (2003)