Herein, we release SMARTpy; a Python suite uniting open-source computational packages in a fully automated workflow for the generation of SMART descriptors. In addition to description of the construction of the SMART cavities we evaluated the impact of probe design on resultant descriptors. Finally, we demonstrate the applicability of SMART descriptors through a series of case studies. This code is freely available and open-sourced on GitHub (). A detailed description of the API is supplied in the Supplementary Information, and all structures analyzed are available in the Git repository.