SMARTY is able to generate multiple different SMARTS patterns matching typical reference atom types in MiniDrugBank. In 10 runs of 10,000 iterations each, we found 16,564 unique SMARTS strings which match at least some fraction of any reference atom type. When we look at the SMARTS patterns which match 100% of any reference atom type, the number is still rather large, at 801 unique SMARTS strings. This was true even for simple atom types, such as CM, which is represented by "[#6X3]" in parm99/parm@Frosst. For CM, SMARTY found 24 different SMARTS strings that matched 100% of this reference atom type. Some of these 24 SMARTS are very generic, such as "[#6]", others more complex ("[#6X3$(*-[*])$(*=[#6])]"). Our goal was not to replicate exactly the same SMARTS patterns written by human experts, but instead to determine what extent automated sampling can capture equivalent -or at least similar -chemical perception. SMARTY's ability to discover a wide diversity of SMARTS patterns corresponding to each reference atom type appears to demonstrate success in this regard. We illustrate how SMARTY scores working atom types (red on the left) compared to reference atom types (blue on the right) using a bipartite graph. (a) When there is only one generic SMARTS string ("[#6]"), this pattern is assigned to both CT and CA atom types through the PATTY-adapted scheme, but it will be matched only to the more populated reference atom type (CT highlighted in yellow); (b) when SMARTY creates a new set of working types, containing both "[#6]" and "[#6X4]", the generic atom type will not match CT anymore, since it chemically matches the new working atom type ("[#6X4]") instead.