(A) (E) (B) (C) (F) (D) Control HLM MLM Chemical synthesis M6

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(A) (E) (B) (C) (F) (D) Control HLM MLM Chemical synthesis M6 350 400 450 500 550 600 650 m/z 10 20 30 40 50 60 70 80 90 100 Relative Abundance 614.2 573.2 554.2 588.2 617.3 534.2 397.1 516.7 480.0 466.1 416.2 369.0 [M+H-H2O]+ 588 573 604.2 588.3 617.1 531.2 466.0 517.3 375.2 415.3 637.5 438.0 5 15 25 18.44 19.35 16.45 21.28 15.63 24.89 10.62 7.40 5.91 3.22 18.46 16.60 19.86 10.41 15.57 9.05 23.61 27.05 6.61 4.46 23.64 19.53 24.06 25.49 15.65 13.52 10.79 9.92 7.44 5.50 26.99 4.59 1.07 27.95 Time (min) 16.56 21.18 9.13 23.73 6.53 25.78 4.13 (A) (B) (C) (D) HLM MLM Chemical synthesis Control (E) (F) M6 Supplemental Figure 4. Extract ion (m/z 632 → 614) chromatograms obtained from LC-LTQ MS analysis of microsomal incubations containing LIM, NAC, NAL, and NADPH in the absence microsomes (A), or in presence of HLMs (B) or MLMs (C). (D) Extracted ion (m/z 632 → 614) chromatogram obtained from LC-LTQ MS analysis of synthetic M6. (E) MS/MS spectrum of M6 generated in microsomal incubations. (F) MS/MS spectrum of synthetic M6.