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

• ChemBase ID: 177289
• Molecular Formular: C20H24N2O4
• Molecular Mass: 356.41556
• Monoisotopic Mass: 356.17360726
• SMILES: c1(ccc2c(c1)c(cc[n+]2[O-])[C@H]([C@H]1[N@+]2(CC[C@@H](C1)[C@H](C2)C=C)[O-])O)OC
• Canonical SMILES: C=C[C@H]1C[N@+]2([O-])CC[C@H]1C[C@H]2[C@@H](c1cc[n+](c2c1cc(OC)cc2)[O-])O
• InChI: InChI=1S/C20H24N2O4/c1-3-13-12-22(25)9-7-14(13)10-19(22)20(23)16-6-8-21(24)18-5-4-15(26-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+,22+/m0/s1
• InChIKey: BTIIQUQYRAFYJP-CURGQOQWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 101655-92-9
• PubChem SID: 164233199
• PubChem CID: 71751938

CALCULATED PROPERTIES

• Acid pKa: 13.227551
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.29005525
• LogD (pH = 7.4): 0.29006878
• Log P: 0.2900696
• Molar Refractivity: 100.646 cm^3
• Polarizability: 38.90863 Å^3
• Polar Surface Area: 81.8 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Beige Solid
• Melting Point: 137-142°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Q694005

A metabolite of Quinine.

REFERENCES

• Christie, D.J., et al.: J. Lab. Clin. Med., 112, 92 (1988).