4-[(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]-6-(2H3)methoxyquinolin-1-ium-1-olate

• ChemBase ID: 177291
• Molecular Formular: C20H24N2O3
• Molecular Mass: 340.41616
• Monoisotopic Mass: 340.17869264
• SMILES: c1(ccc2c(c1)c(cc[n+]2[O-])[C@H]([C@H]1N2CC[C@@H](C1)[C@H](C2)C=C)O)OC
• Canonical SMILES: C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1cc[n+](c2c1cc(OC)cc2)[O-])O
• InChI: InChI=1S/C20H24N2O3/c1-3-13-12-21-8-6-14(13)10-19(21)20(23)16-7-9-22(24)18-5-4-15(25-2)11-17(16)18/h3-5,7,9,11,13-14,19-20,23H,1,6,8,10,12H2,2H3/t13-,14-,19-,20+/m0/s1
• InChIKey: GBBIANHNFAPFOH-WZBLMQSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]-6-(^2H₃)methoxyquinolin-1-ium-1-olate
• IUPAC Traditional name: 4-[(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]-6-(^2H₃)methoxyquinolin-1-ium-1-olate
• Synonyms: (8α,9R)-6'-(Methoxy-d3)-cinchonan-9-ol 1'-Oxide; Quinine-d3 1'-N-Oxide; Quinine-d3 N'-Oxide; Quinine-d3 ar-N-Oxide; Quinine-d3 1'-Oxide

Database IDs

• PubChem SID: 164233201
• PubChem CID: 71751939

CALCULATED PROPERTIES

• Acid pKa: 13.805381
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.7064064
• LogD (pH = 7.4): -0.051033214
• Log P: 1.4144448
• Molar Refractivity: 98.6011 cm^3
• Polarizability: 38.787193 Å^3
• Polar Surface Area: 58.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - Q694012

A labelled metabolite of Quinine.

REFERENCES

• Small, D.L., J. Chem. Med., 22,1014 (1979)
• Guentert, T.W., et al.: Eur. J. Drug Metab. Pharmacokinet., 7, 31 (1979)
• Chang, Y.F., et al.: Neurochem. Res., 13, 455 (1979)