2-({4-[(3-ethynylphenyl)amino]-7-(2-methoxyethoxy)quinazolin-6-yl}oxy)acetic acid

• ChemBase ID: 166557
• Molecular Formular: C21H19N3O5
• Molecular Mass: 393.39266
• Monoisotopic Mass: 393.13247072
• SMILES: c1c(c(cc2c1c(ncn2)Nc1cc(ccc1)C#C)OCCOC)OCC(=O)O
• Canonical SMILES: COCCOc1cc2ncnc(c2cc1OCC(=O)O)Nc1cccc(c1)C#C
• InChI: InChI=1S/C21H19N3O5/c1-3-14-5-4-6-15(9-14)24-21-16-10-18(29-12-20(25)26)19(28-8-7-27-2)11-17(16)22-13-23-21/h1,4-6,9-11,13H,7-8,12H2,2H3,(H,25,26)(H,22,23,24)
• InChIKey: KNCLPBMNMFPIIO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({4-[(3-ethynylphenyl)amino]-7-(2-methoxyethoxy)quinazolin-6-yl}oxy)acetic acid
• IUPAC Traditional name: ({4-[(3-ethynylphenyl)amino]-7-(2-methoxyethoxy)quinazolin-6-yl}oxy)acetic acid
• Synonyms: 2-[[4-[(3-Ethynylphenyl)amino]-6-(2-methoxyethoxy)-7-quinazolinyl]oxy]acetic Acid; Desmethyl Erlotinib Carboxylate Acid

Database IDs

• CAS Number: 882172-60-3
• PubChem SID: 162260690
• PubChem CID: 71315775

CALCULATED PROPERTIES

• Acid pKa: 3.009907
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.3512639
• LogD (pH = 7.4): -0.7287374
• Log P: 1.1598034
• Molar Refractivity: 102.827 cm^3
• Polarizability: 41.12336 Å^3
• Polar Surface Area: 102.8 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292800

A metabolite of Erlotinib (E625000).

REFERENCES

• Hidalgo, M., et al.: J. Clin. Oncol., 19, 3267 (2001)
• Austin, R., et al.: Drug Metab. Dispos., 30, 1497 (2001)
• Howgate, E., et al.: Xenobiotica, 36, 473 (2001)