ethyl 4-hydroxy-6,7-bis(2-methylpropoxy)quinoline-3-carboxylate

• ChemBase ID: 179729
• Molecular Formular: C20H27NO5
• Molecular Mass: 361.43208
• Monoisotopic Mass: 361.18892297
• SMILES: c1(c(c2c(nc1)cc(c(c2)OCC(C)C)OCC(C)C)O)C(=O)OCC
• Canonical SMILES: CCOC(=O)c1cnc2c(c1O)cc(c(c2)OCC(C)C)OCC(C)C
• InChI: InChI=1S/C20H27NO5/c1-6-24-20(23)15-9-21-16-8-18(26-11-13(4)5)17(25-10-12(2)3)7-14(16)19(15)22/h7-9,12-13H,6,10-11H2,1-5H3,(H,21,22)
• InChIKey: LVVXOXRUTDAKFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-hydroxy-6,7-bis(2-methylpropoxy)quinoline-3-carboxylate
• IUPAC Traditional name: ethyl 4-hydroxy-6,7-bis(2-methylpropoxy)quinoline-3-carboxylate
• Synonyms: Antagonal; Bonaid; Butoril; Buquinolate

Database IDs

• CAS Number: 5486-03-3
• PubChem SID: 164235639
• PubChem CID: 21651

CALCULATED PROPERTIES

• Acid pKa: 10.763948
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.0107574
• LogD (pH = 7.4): 5.010697
• Log P: 5.010884
• Molar Refractivity: 99.1489 cm^3
• Polarizability: 39.894005 Å^3
• Polar Surface Area: 77.88 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Product Information

• Application(s): Anticoccidial agent for poultry; Protozoacide

REFERENCES

• Spencer, C.F. et al., J. Med. Chem., 1966, 9, 934, (synth, pharmacol)
• Raines, T.V., Poultry Sci., 1968, 47, 1425, (rev)
• Egri, J. et al., Acta Chim. Acad. Sci. Hung., 1972, 73, 469; 74, 345; 351, (synth, pharmacol)
• Harris, N.D., Synthesis, 1972, 625, (synth)
• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, BOO632