(S)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

• ChemBase ID: 164767
• Molecular Formular: C19H22N2O
• Molecular Mass: 294.39078
• Monoisotopic Mass: 294.17321333
• SMILES: c1ccc2nccc(c2c1)[C@@H]([C@H]1N2CCC(C1)[C@H](C2)C=C)O
• Canonical SMILES: C=C[C@H]1CN2CCC1C[C@H]2[C@H](c1ccnc2c1cccc2)O
• InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14?,18-,19-/m0/s1
• InChIKey: KMPWYEUPVWOPIM-SIGHOMJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (S)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• IUPAC Traditional name: (S)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
• Synonyms: (8α,9S)-Cinchonan-9-ol; Epicinchonidine; (+)-9-epi-Cinchonidine; 9-epi-Cinchonidine

Database IDs

• CAS Number: 550-54-9
• PubChem SID: 162258902
• PubChem CID: 6713950

CALCULATED PROPERTIES

• Acid pKa: 13.8773155
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.60487753
• LogD (pH = 7.4): 0.92435837
• Log P: 2.6711352
• Molar Refractivity: 88.2304 cm^3
• Polarizability: 35.8717 Å^3
• Polar Surface Area: 36.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C441930

The 9-epimer of Cinchonidine (C441925). Antimalarial.

REFERENCES

• Litchfield, J., et al.: J. Pharm. Exp. Ther., 96, 99 (1949)
• Trager, W., et al.: Science, 193, 673 (1949)
• Panisko, D., et al.: Drugs, 39, 160 (1949)
• Karle, J., et al.: Antimicrob. Agents Chemother., 36, 1538 (1949)