(A) (E) (B) (C) (F) (D) Control HLM MLM Chemical synthesis M4 M4'

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(A) (E) (B) (C) (F) (D) Control HLM MLM Chemical synthesis M4 M4' 5 10 15 20 25 30 40 60 80 100 Relative Abundance 9.58 8.46 3.91 11.47 12.15 24.31 16.21 22.45 25.70 20.18 9.60 8.58 3.95 11.48 3.04 12.49 15.85 19.78 25.30 23.04 25.04 25.16 24.04 16.26 25.94 17.83 22.87 15.06 12.06 22.08 10.07 7.67 26.85 5.81 4.70 2.92 Time (min) 9.49 8.38 3.83 10.65 12.74 16.00 25.25 19.48 22.41 26.69 300 400 500 600 700 800 900 1000 1100 1200 m/z 50 70 90 936.4 990.4 874.4 816.3 687.3 741.3 544.2 1047.5 403.3 643.4 517.1 313.1 1128.4 874.3 544.1 1047.6 653.3 375.2 442.1 1195.1 1092.3 (A) (B) (C) (D) HLM MLM Chemical synthesis Control [M+H-H2O]+ (E) (F) 990 936 -H2O-CO2 874 M4' M4 Supplemental Figure 3. Extract ion (m/z 1065 → 936) chromatograms obtained from LC-LTQ MS analysis of microsomal incubations containing LIM, GSH, NAL, and NADPH in the absence microsomes (A), or in presence of HLMs (B) or MLMs (C). (D) Extracted ion (m/z 1065 → 936) chromatogram obtained from LC-LTQ MS analysis of synthetic M4 and M4'. (E) MS/MS spectrum of M3 generated in microsomal incubations (M4' showed the same MS/MS spectrum). (F) MS/MS spectrum of synthetic M4 (synthetic M4' showed the same MS/MS spectrum).