2-{[(4S)-4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino}ethan-1-ol

• ChemBase ID: 170331
• Molecular Formular: C18H26ClN3O
• Molecular Mass: 335.87154
• Monoisotopic Mass: 335.17644015
• SMILES: c1c(cc2c(c1)c(ccn2)N[C@H](CCCN(CCO)CC)C)Cl
• Canonical SMILES: OCCN(CCC[C@@H](Nc1ccnc2c1ccc(c2)Cl)C)CC
• InChI: InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)/t14-/m0/s1
• InChIKey: XXSMGPRMXLTPCZ-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(4S)-4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino}ethan-1-ol
• IUPAC Traditional name: 2-{[(4S)-4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino}ethanol
• Synonyms: (S)-2-[[4-[(7-Chloro-4-quinolinyl)amino]pentyl]ethylamino]ethanol Phosphate; (S)-(+)-Hydroxy Chloroquine Diphosphate

Database IDs

• CAS Number: 158749-76-9
• PubChem SID: 164226241
• PubChem CID: 178396

CALCULATED PROPERTIES

• Acid pKa: 15.59329
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.7593226
• LogD (pH = 7.4): 0.3267855
• Log P: 2.8869712
• Molar Refractivity: 97.9667 cm^3
• Polarizability: 38.672028 Å^3
• Polar Surface Area: 48.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H905305

A major metabolite of Chloroquine (C379965).

REFERENCES

• Brocks, D., et al.: Clin. Pharmacokinet., 42, 1359 (2003)
• Brocks, D., et al.: Clin. Pharmacokinet., 42, 1359 (2003)
• Huang, S., et al.: Talanta, 64, 887 (2003)