1-({5-[(7-chloroquinolin-4-yl)amino]-2-hydroxyphenyl}methyl)pyrrolidin-1-ium-1-olate

• ChemBase ID: 160570
• Molecular Formular: C20H20ClN3O2
• Molecular Mass: 369.8447
• Monoisotopic Mass: 369.12440458
• SMILES: c1c(cc2c(c1)c(ccn2)Nc1ccc(c(c1)C[N+]1(CCCC1)[O-])O)Cl
• Canonical SMILES: Clc1ccc2c(c1)nccc2Nc1ccc(c(c1)C[N+]1([O-])CCCC1)O
• InChI: InChI=1S/C20H20ClN3O2/c21-15-3-5-17-18(7-8-22-19(17)12-15)23-16-4-6-20(25)14(11-16)13-24(26)9-1-2-10-24/h3-8,11-12,25H,1-2,9-10,13H2,(H,22,23)
• InChIKey: VLCOGSMGGJRHOM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-({5-[(7-chloroquinolin-4-yl)amino]-2-hydroxyphenyl}methyl)pyrrolidin-1-ium-1-olate
• IUPAC Traditional name: 1-({5-[(7-chloroquinolin-4-yl)amino]-2-hydroxyphenyl}methyl)pyrrolidin-1-ium-1-olate
• Synonyms: 4-[(7-Chloro-4-quinolinyl)amino]-2-[(1-oxido-1-pyrrolidinyl)methyl]phenol; 4-[(7-Chloro-4-quinolinyl)amino]-2-(1-pyrrolidinylmethyl)phenol N2-Oxide; Amopyroquine N-Oxide

Database IDs

• CAS Number: 172476-17-4
• PubChem SID: 162254705
• PubChem CID: 46780377

CALCULATED PROPERTIES

• Acid pKa: 10.096647
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.2367067
• LogD (pH = 7.4): 3.0478287
• Log P: 3.0941246
• Molar Refractivity: 103.3798 cm^3
• Polarizability: 40.265564 Å^3
• Polar Surface Area: 72.03 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A634220

A non-polar potential metabolite of Amopyroquine.

REFERENCES

• Aitken, D.J., et al.: Bioorg. Med. Chem. Lett., 5, 1111 (1995)