While SMARTY and SMIRKY both show considerable promise, they both face challenges with the size of the combinatorial search problem, suggesting room for further improvement. The combinatorial problem becomes especially important for fragment types involving the most potential atoms and decoratorsangles and torsions. One step to improving performance could include a better optimization algorithm, such as simulated annealing. Here, however, the sampling problem is exacerbated by the fact that move proposals are not necessarily chemically sensible, so future work will need to make more reasonable chemical moves to improve efficiency. Before introducing a new optimization algorithm, the move set needs to be improved. Particularly, instead of using any SMARTS decorator, these tools should take advantage of basic chemistry. For example, no molecule will have a tetrahedral carbon with a double bond, so such a move should never be proposed.