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. Author manuscript; available in PMC: 2021 Dec 30.
Published in final edited form as: J Chem Inf Model. 2018 Jul 23;58(8):1483–1500. doi: 10.1021/acs.jcim.8b00104

Figure 8.

Figure 8.

Some PAINS filters may be associated with other, unrelated reactive motifs. (A) The imine_one_fives filter group matches a five-membered ring motif containing both imine and ketone groups. Among 102 compounds matching this filter group (red), 28 (27%) contain a thioamide group conjugated to the ring motif (purple). (B) Compounds matching the filter group and this thioamide group are enriched 3.31-fold for promiscuous actives compared to compounds matching only the filter group (p = 7.97 × 10−3, χ2 test). (C) Compounds containing the thioamide group are assigned higher reactivity scores than compounds matching only the filter group (p < 10−10, Mann–Whitney U-test). (D) Oxidation of the thioamide group is known to form a reactive intermediate that can conjugate to proteins in rat hepatocytes.73 **: p < 0.001. ***: p < 0.0001.