SMARTpy performs a template-based conformational search that generates an ensemble representative of the topology of the cavity. The choice of molecular probe is shown to influence the information obtained from SMART parameters. Acyclic probes are shown to generate highly irregular cavities, parametrizing the space between ligands. Macrocyclic probes generate regular, more spherical pockets due to rotational barriers. The flexibility of macrocyclic probes can be increased by the selection of small substituents bound to the core, such as H. This allows the probe to explore space closer to the ligands, resulting in a "high definition" representation of the cavity. Depending on the flexibility of the substrates coming together within the pocket in the transformation of interest, smaller or larger probes may be more suitable for generating SMART descriptors.