We first tested SMARTY on the AlkEthOH and PhEthOH sets. Although these have only eight atom types, some of the five hydrogen types used in these sets require multiple atoms in the beta position, so they still provide a significant challenge. For the AlkEthOH set run at effective temperatures between 10 -6 and 10 -2 , the original sampler, SMARTY , yielded total scores, averaged across the 10 runs, of > 90% (Table ), and the lowest average score is still fairly high, at 69%. The degradation of performance at lower and higher temperatures is reasonable for the MC method, as low temperatures can lead to trapping in local maxima, while high temperatures can lead to a lower preference for favorable states. Figure provides sample plots of total score against step number for MC runs at various temperatures. As expected, the higher temperatures lead to greater score fluctuations. Equivalent results were obtained for the PhEthOH set (Table ), which has a similar number of atom types (Section 2.4). To summarize results, we also report total scores for the initial atom types used in each simulation and the maximum total score received across all simulations (Table ). Overall, these results strongly support the ability of SMARTY to sample chemically relevant ensembles of atom types. Analysis of the partial scores offers a finer-grained view of these overall results. Thus, we made heat maps showing the frequency of generating a partial score of 100% for each reference atom type (Figure ), at the various simulation temperatures. These show that some reference atom types are easier to discover than others. This can be for multiple reasons, including because they have simpler specifications, and because they occur more frequently. Also, although low to moderate temperatures yield the best results for most atom types, higher temperatures worked better for atom type HC, at least for the PhEthOH molecule set.