Multidrug resistance activities pEC 50 of sensitive, resistant, and moderately resistant strains of the pathogenic fungus Penicillium digitatum against triflumizole, fenarimol, bitertanol, pyrifenox, cycloheximide, acriflavine, and 4-nitroquinoline-N-oxide were studied by principal component and hierarchical cluster analyses. Genome descriptors for fungal cytochrome P450 sterol 14a-demethylase and multidrug efflux pump PMR1 were generated and correlated with pEC 50 by partial least squares. Toxicants were modeled at the PM3 level. Novel Activity -Structure Relationships (ASRs) were established to predict toxicant structural features from biological activities and to identify and classify the strains. New types of relationships to model and predict biological activities are Quantitative Genome -Activity Relationship (QGAR) and Quantitative Genome/ Structure -Activity Relationship (QGSAR