In summary, we report a series of computational and statistical methods that enabled prediction of decomposition temperature and impact sensitivity across a structurally diverse scope of tetrazole and azide HEMs. The key conceptual innovation in this approach is the decision to interrogate the structural and quantum mechanical properties of HEMs at the level of their explosophores, providing the ability to describe and interpret mechanistic events leading to decomposition while also modeling sensitivity properties. The advantages of this descriptor suite are compounded by the fact that descriptors are localized at the level of individual chemical bonds but can readily be expanded to larger chemical motifs, allowing a common set of parameters to be generated for an explosophore of user-specified structure and a sensitivity property of interest. A comprehensive account of the computational methods used to construct these models is disclosed in the SI.