Computed dirhodium(II) catalyst structures from a study by Shaw and Sigman 7 were used to assess the impact of probe features on SMART descriptors. A subset of conformers was selected with symmetrical, asymmetrical, and chiral ligands with the intent to maximize representative ligand feature diversity (Figure SX). All molecular probes (Table ) employed for analysis have tetrahedral Si core atoms functionalized with either H or F. The tether atom that binds to the structure is S with a dummy H atom that is removed after initial docking. The choice of Si was initially practical for ease of pocket manipulation in UCSF Chimera with the legacy method, but many molecular units can now be used as a molecular probe core using SMARTpy.