(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-methyl-4-[(1R)-3-[(2H3)methylamino]-1-phenylpropoxy]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 170136
• Molecular Formular: C23H29NO8
• Molecular Mass: 447.47826
• Monoisotopic Mass: 447.18931689
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)O)Oc1cc(c(cc1)O[C@H](CCNC)c1ccccc1)C)O)O)O
• Canonical SMILES: CNCC[C@H](c1ccccc1)Oc1ccc(cc1C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H29NO8/c1-13-12-15(30-23-20(27)18(25)19(26)21(32-23)22(28)29)8-9-16(13)31-17(10-11-24-2)14-6-4-3-5-7-14/h3-9,12,17-21,23-27H,10-11H2,1-2H3,(H,28,29)/t17-,18+,19+,20-,21+,23-/m1/s1
• InChIKey: DJWNPJFKTPNTAE-AJYYVVFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-methyl-4-[(1R)-3-[(^2H₃)methylamino]-1-phenylpropoxy]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-methyl-4-[(1R)-3-[(^2H₃)methylamino]-1-phenylpropoxy]phenoxy}oxane-2-carboxylic acid
• Synonyms: 3-Methyl-4-[(1R)-3-(methylamino)-1-phenylpropoxy]phenyl β-D-Glucopyranosiduronic Acid-d3; 4-Hydroxyatomoxetine-O-glucuronide-d3; 4'-Hydroxy Atomoxetine β-D-Glucuronide-d3

Database IDs

• PubChem SID: 164226046
• PubChem CID: 71748823

CALCULATED PROPERTIES

• Acid pKa: 2.8910086
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.9149456
• LogD (pH = 7.4): -0.9156205
• Log P: -0.9143829
• Molar Refractivity: 113.4277 cm^3
• Polarizability: 45.383884 Å^3
• Polar Surface Area: 137.71 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H802512

A metabolite of labelled Atomoxetine (A791400).

REFERENCES

• Wong, D., et al.: J. Pharmacol. Exp. Ther., 222, 61 (1982)
• Steiner, E., et al.: Clin. Pharmacol. Ther., 44, 431 (1982)
• Gehlert, D., et al.: Neurosci. Lett., 157, 203 (1982)
• Kuczenski, R., et al.: J. Neurochem., 68, 2032 (1982)
• Sauer, J., et al.: Drug