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. Author manuscript; available in PMC: 2018 Apr 17.
Published in final edited form as: Chem Res Toxicol. 2017 Mar 14;30(4):1046–1059. doi: 10.1021/acs.chemrestox.6b00336

Figure 3.

Figure 3

Commonly observed structural alerts that bioactivation can render toxic. Our furan, phenol, nitroaromatic, and thiophene structural alert evaluation sets contain 17, 188, 37, and 42 FDA approved or withdrawn small molecule drugs (in purple), respectively. Among those, 13 furan-, 127 phenol-, 31 nitroaromatic-, and 31 thiophene-containing drugs have been metabolically studied (blue and red). Of those metabolically studied drugs, the furan, phenol, nitroaromatic, and thiophene structural alerts are bioactivated, respectively, 23%, 26%, 51%, and 26% of the time. Nitroaromatics can include aromatic rings of any size, so only a fragment of the ring is visualized.