SMARTY and SMIRKY have proven capable of automatically sampling chemical perception trees relevant to general small molecule force fields. Both of our tools were tested first with relatively simple sets (AlkEthOH and PhEthOH) and then using MiniDrugBank, which provided a test set of molecules encompassing the diversity of the DrugBank database. SMARTY generated SMARTS patterns which resulted in a 93% total score for MiniDrugBank, and 100% for AlkEthOH and PhEthOH. SMIRKY achieved a total score of over 90% for nonbonded, bond, and angle fragment types in MiniDrugBank.