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. Author manuscript; available in PMC: 2018 Mar 27.
Published in final edited form as: Chem Res Toxicol. 2017 Feb 2;30(2):642–656. doi: 10.1021/acs.chemrestox.6b00385

Figure 13.

Figure 13

Examples of drugs associated with idiosyncratic toxicity that received high molecule quinone formation scores (MQS) but are not known to form quinones in our data set. Each drug predicted to form a quinone is visualized above its most similar quinone-forming molecule from the training data. Similarity was quantified using path based fingerprints and MinMax similarity, a modification of Tanimoto appropriate for count fingerprints.107 Top, flecainide (MQS: 0.81), thenalidine (MQS: 0.79), and bunamiodyl (MQS: 0.96). Bottom, a remoxipride metabolite (MQS: 0.58),108 thioridazine (MQS 0.36),101 and a flutamide metabolite (MQS 0.88).109 The atoms of experimentally observed quinone forming pairs are circled. Scores (ranging from 0 to 0.99) are indicated by colored shading, assigning each atom the probabilistic OR of all pair-level quinone formation scores including the atom. For the training examples, cross-validated scores are reported.