MiniDrugBank covers significantly more chemical space than either of the other molecule sets with 73 bond, 34 angle, 136 proper torsion, and 26 nonbonded parameters from smirnoff99Frosst. It uses all parameters employed in molecules from the DrugBank database that can be atom typed by the parm99/parm@Frosst force field, as described in Section 2.4. This is a more complex set, so despite considerable success, we are often unable to obtain a total score of 100%. Specifically, we were unable to find a total score of 100% for bonds, angles, torsions or nonbonded fragment types with 10,000 iterations. We also saw a significant decrease in the average total score for all fragment types during our ten simulations (Table ) relative to other molecule sets. For this reason we repeated the simulations with 50,000 and then 100,000 iterations. SMIRKY still did not find a total score of 100% during the longer simulations. However, overall, SMIRKY was partially successful for MiniDrugBank. We achieve total scores over 90% for nonbonded, bond, and angle types for the highest scoring iterations (Table ). The highest total score for torsion types is 76%, which is still promising considering the large combinatorial problem.