Figure 9.

Metabolism model identifies which nitroaromatics (highlighted in red) are bioactivated. Twelve examples from the nitroaromatic evaluation set, from left to right, top to bottom: nitrofurantoin,¹⁰⁸ furazolidone,¹⁰⁹ clonazepam,⁵⁴ tolcapone,⁵¹ dantrolene,^52,110 nimesulide,⁵² flutamide,⁵² entacapone,^106,111 tinidazole,¹¹² nifedipine,⁵⁴ benidipine, and lercanidipine. The remaining molecules and their prediction are reported in the Supporting Information (Table S3). Site reduction scores are indicated by color shading, ranging from red (1.0 highly probable) to white (0.0, low probability). Experimentally observed sites of reduction are indicated by white circles. Attached numbers are molecule reduction scores. The reduction model was able to assign drugs that are known to be bioactivated at nitroaromatic structural alerts (scores in red) with higher scores than those that do not (scores in blue). The model AUC accuracy on the nitroaromatic evaluation set is 93% (significantly outperforms the structural alert approach, two-sided p-value = 0.0002).