Spatial Molding for Approachable Rigid Targets (SMART) descriptors quantify structural features at the reactive pockets of catalysts, such as cavity volume (VCAVITY), entry surface area (ESA), and contact surface area (CSA) with the surrounding ligands. These descriptors are obtained through conformational sampling of reactive site space using a generalized molecular probe. SMART descriptors were initially applied to quantify the origins of regioselectivity in dirhodium C-H functionalization of donor/acceptor carbenes and diastereoselectivity in dirhodium C-H insertion of donor/donor carbenes 7 . Although we envisioned broader applicability to diverse areas of catalysis, the original implementation of SMART was challenging for widespread adoption, including a significant reliance on user input and the necessity for commercial software. These two factors have prevented the rapid analysis of larger data sets and limited the accessibility of the tool to a broader community of potential users.