TABLE 1

Fragmentation patterns of KAE609 and metabolites

Structural characterization of metabolites was carried out by LC-MS/MS analysis with accurate mass measurements. The proposed structures of the metabolites were based on their elemental composition derived from accurate mass measurements and fragment ions in their data-dependent MS² and MS³ mass spectra. Comparison of metabolite fragment ions with those of KAE609 allowed the assignment of regions of biotransformation.

Compound	[MH⁺] m/z	Elemental Formula	Diagnostic Fragment Ions
KAE609	390.0573	C₁₉H₁₅Cl₂FN₃O	390, 347,^{^a} 319,^{^a} 311, 312, 284, 276
M14	404.0362	C₁₉H₁₃Cl₂FN₃O₂	404, 386,^{^a} 360, 351, 325, 278
M18	388.0416	C₁₉H₁₃Cl₂FN₃O	388, 359,^{^a} 324
M20	404.0375	C₁₉H₁₃Cl₂FN₃O₂	404,^{^a} 375, 340
M20.1	388.0425	C₁₉H₁₃Cl₂FN₃O	388, 360,^{^a} 324
M21.2	404.0375	C₁₉H₁₃Cl₂FN₃O₂	404,^{^a} 375,^{^a} 368,^{^a} 340,^{^a} 312
M23	404.0363	C₁₉H₁₃Cl₂FN₃O₂	404, 375, 340, 235
M24	404.0362	C₁₉H₁₃Cl₂FN₃O₂	404, 375, 340, 235
M26	406.0515	C₁₉H₁₅Cl₂FN₃O₂	406,^{^a} 373, 327, 226^{^a}
M34	406.0528	C₁₉H₁₅Cl₂FN₃O₂	406, 373,^{^a} 355,^{^a} 309,^{^a} 210^{^a}
M36	404.0042	C₁₉H₁₃Cl₂FN₃O₂	404,^{^a} 375
M37	390.0579	C₁₉H₁₅Cl₂FN₃O	390, 373, 210,^{^a} 175
M39	404.037	C₁₉H₁₃Cl₂FN₃O₂	404, 355,^{^a} 337,^{^a} 319
M40	388.0419	C₁₉H₁₃Cl₂FN₃O	388,^{^a} 359, 324, 210
M44	402.0223	C₁₉H₁₁Cl₂FN₃O₂	402,^{^a} 339, 325, 197,^{^a} 172
M46	402.0209	C₁₉H₁₁Cl₂FN₃O₂	402,^{^a} 310, 276, 172
M47	401.9908	C₁₉H₁₁Cl₂FN₃O₂	402,^{^a} 367, 310
M48	386.0256	C₁₉H₁₁Cl₂FN₃O	386,^{^a} 351, 323, 309

↵^a Indicates the most abundant fragment ions.