4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol

• ChemBase ID: 166466
• Molecular Formular: C19H22N2O2
• Molecular Mass: 310.39018
• Monoisotopic Mass: 310.16812795
• SMILES: c1(ccc2c(c1)c(ccn2)[C@H]([C@H]1N2CCC(C1)[C@H](C2)C=C)O)O
• Canonical SMILES: C=C[C@H]1CN2CCC1C[C@H]2[C@@H](c1ccnc2c1cc(O)cc2)O
• InChI: InChI=1S/C19H22N2O2/c1-2-12-11-21-8-6-13(12)9-18(21)19(23)15-5-7-20-17-4-3-14(22)10-16(15)17/h2-5,7,10,12-13,18-19,22-23H,1,6,8-9,11H2/t12-,13?,18-,19+/m0/s1
• InChIKey: VJFMSYZSFUWQPZ-BPBOJLQBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol
• IUPAC Traditional name: 4-[(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](hydroxy)methyl]quinolin-6-ol
• Synonyms: (8,9R)-9-Diol Cinchonan-6’; Cupreine; O-Demethylquinidine; Ultraquinine; O-Desmethyl Quinine

Database IDs

• CAS Number: 524-63-0
• PubChem SID: 162260599
• PubChem CID: 441075

CALCULATED PROPERTIES

• Acid pKa: 9.756925
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.86843485
• LogD (pH = 7.4): 0.71408486
• Log P: 1.958033
• Molar Refractivity: 90.2113 cm^3
• Polarizability: 36.43055 Å^3
• Polar Surface Area: 56.59 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: >171°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292145

A metabolite of Quinine (Q694000).

REFERENCES

• Small, D.L., et al.: J. Chem. Med., 22, 1014 (1979)
• Guentert, T.W., et al.: Eur. J. Drug Metab. Pharmacokinet., 7, 31 (1979)
• Rakhir, A., et al.: J. Pharmacokinet. Biopharm., 12, 1 (1979)
• Christie, D.J., et al.: J. Lab. Clin. Med., 112, 92 (1979)