Discrete Element Modeling (DEM) of rock subject to high confining pressures, such as in a subterranean drilling environment, may be used to predict performance of cutting structures used in drill bits and other drilling tools, as well as of the tools themselves. DEM may also be used to create “virtual” rock exhibiting specific drillability characteristics with or without specific reference to any actual rock, for purposes of assessing cutting efficiency of various cutting structure configurations and orientations, as well as of drilling tools incorporating same.