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. 2014 Aug 26;54(9):2423–2432. doi: 10.1021/ci500363p

Table 4. Frequency of Application of Ring–Chain Rules in the Systematic Generation of Ring–Chain Tautomers in AMS Database.

SMIRKS rule count %
3-exo-trig 65 435 0.31
4-exo-trig 10 560 0.05
5-exo-trig 7 506 722 35.09
6-exo-trig 5 289 114 24.72
7-exo-trig 4 185 292 19.56
5-exo-dig 179 567 0.84
6-exo-dig 472 074 2.21
7-exo-dig 3 293 445 15.40
5-endo-trig 169 007 0.79
6-endo-trig 156 371 0.73
7-endo-trig 65 239 0.30