(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-(2,2,5,5-2H4)oxolan-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide

• ChemBase ID: 159581
• Molecular Formular: C24H25ClFN5O3
• Molecular Mass: 485.9384032
• Monoisotopic Mass: 485.16299559
• SMILES: c1(c(cc2c(c1)ncnc2Nc1cc(c(cc1)F)Cl)NC(=O)/C=C/CN(C)C)O[C@H]1CCOC1
• Canonical SMILES: CN(C/C=C/C(=O)Nc1cc2c(ncnc2cc1O[C@@H]1COCC1)Nc1ccc(c(c1)Cl)F)C
• InChI: InChI=1S/C24H25ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/b4-3+/t16-/m0/s1
• InChIKey: ULXXDDBFHOBEHA-CWDCEQMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-(2,2,5,5-^2H₄)oxolan-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
• IUPAC Traditional name: (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-(2,2,5,5-^2H₄)oxolan-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
• Synonyms: (2E)-N-[4-[(3-Chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-butenamide; BIBW 2992; Afatinib-d4

Database IDs

• PubChem SID: 162253716
• PubChem CID: 71313050

CALCULATED PROPERTIES

• Acid pKa: 12.487393
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.6314944
• LogD (pH = 7.4): 2.3384943
• Log P: 3.7583613
• Molar Refractivity: 131.3804 cm^3
• Polarizability: 49.88503 Å^3
• Polar Surface Area: 88.61 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A355302

Labelled Afatinib (A355300). An aminocrotonylamino-substituted quinazoline derivative used for treating cancer and diseases of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder.