2-{[3-({4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)propyl]amino}ethan-1-ol

• ChemBase ID: 166630
• Molecular Formular: C20H22ClFN4O3
• Molecular Mass: 420.8650832
• Monoisotopic Mass: 420.13644648
• SMILES: c1c(c(cc2c1c(ncn2)Nc1cc(c(cc1)F)Cl)OC)OCCCNCCO
• Canonical SMILES: OCCNCCCOc1cc2c(ncnc2cc1OC)Nc1ccc(c(c1)Cl)F
• InChI: InChI=1S/C20H22ClFN4O3/c1-28-18-11-17-14(10-19(18)29-8-2-5-23-6-7-27)20(25-12-24-17)26-13-3-4-16(22)15(21)9-13/h3-4,9-12,23,27H,2,5-8H2,1H3,(H,24,25,26)
• InChIKey: WDGXWUJUPXLCDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[3-({4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)propyl]amino}ethan-1-ol
• IUPAC Traditional name: 2-{[3-({4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}oxy)propyl]amino}ethanol
• Synonyms: 2-[[3-[[4-[(3-Chloro-4-fluorophenyl)amino]-7-methoxy-6-quinazolinyl]oxy]propyl]amino]ethanol; 3-Desmorpholinyl-3-hydroxyethylamino Gefitinib

Database IDs

• CAS Number: 847949-56-8
• PubChem SID: 162260763
• PubChem CID: 11235504

CALCULATED PROPERTIES

• Acid pKa: 15.483567
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.34060338
• LogD (pH = 7.4): 0.7449521
• Log P: 2.8963041
• Molar Refractivity: 109.4299 cm^3
• Polarizability: 42.89898 Å^3
• Polar Surface Area: 88.53 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D296835

A metabolite of Gefitinib (G304000).

REFERENCES

• Newton, D., et al.: Drug Metab. Dispos., 23, 154 (1995)
• Wakeling, A., et al.: Cancer Res., 62, 5749 (1995)
• McKillop, D., et al.: Xenobiotica, 34, 917 (1995)