1-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoyl}-3-[(2R)-piperidin-2-yl]azetidin-3-ol

• ChemBase ID: 179604
• Molecular Formular: C21H21F3IN3O2
• Molecular Mass: 531.3100196
• Monoisotopic Mass: 531.06305959
• SMILES: C1(CN(C1)C(=O)c1ccc(c(c1Nc1ccc(cc1F)I)F)F)([C@H]1CCCCN1)O
• Canonical SMILES: Ic1ccc(c(c1)F)Nc1c(ccc(c1F)F)C(=O)N1CC(C1)(O)[C@H]1CCCCN1
• InChI: InChI=1S/C21H21F3IN3O2/c22-14-6-5-13(19(18(14)24)27-16-7-4-12(25)9-15(16)23)20(29)28-10-21(30,11-28)17-3-1-2-8-26-17/h4-7,9,17,26-27,30H,1-3,8,10-11H2/t17-/m1/s1
• InChIKey: BSMCAPRUBJMWDF-QGZVFWFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoyl}-3-[(2R)-piperidin-2-yl]azetidin-3-ol
• IUPAC Traditional name: 1-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoyl}-3-[(2R)-piperidin-2-yl]azetidin-3-ol
• Synonyms: [3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl][3-hydroxy-3-[(2R)-2-piperidinyl]-1-azetidinyl]methanone; (R)-XL 518; (R)-XL518

Database IDs

• CAS Number: 934660-94-3
• PubChem SID: 164235514
• PubChem CID: 16222097

CALCULATED PROPERTIES

• Acid pKa: 12.659646
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.8336506
• LogD (pH = 7.4): 2.7280476
• Log P: 5.035853
• Molar Refractivity: 115.8474 cm^3
• Polarizability: 43.747135 Å^3
• Polar Surface Area: 64.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - X746245

The (R)-enantiomer of the MEK1 inhibitor XL518 (X746250).

REFERENCES

• Rosen, L.S. et al.: J. Clin. Oncol., 26, 14585 (2008)