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Log P partition coefficient of a molecule between an aqueous and lipophilic phases Log S water solubility MACCS molecular ACCess System MW molecular weight N.S nonsignificant NPV negative predictive value PAMPA parallel artificial membrane permeability assay P -gp P -glycoprotein PPV positive predicted value RBs rotatable bonds ROC responder operator curve SLCs solute carriers SMARTS list of substructure patterns TPSA topological polar surface area t SNE t -distributed stochastic neighbor embedding XGBoost eXtreme gradient boosting Data Availability Statement All data and written scripts can be found at Supporting Information Available The Supporting Information is available free of charge at Overview of similarities between datasets and chemical space analysis based on physiochemical properties and fingerprints per dataset, confusion matrices and corresponding AUCs of physiochemical property models, confusion matrices and corresponding AUCs of MACCS fingerprint models, confusion matrices and corresponding AUCs of physiochemical property and structural feature models, decision tree MACCS fingerprint models, compounds’ Tanimoto similarity search, analysis of the CNS dataset for the TNs for all models, detailed MACCS structural analysis of the molecular influx model, and overview of the performance of all XGBoost models (PDF) Author Contributions ⊥ F.M.G.C

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The average of SF36 Vitality, Role Physical and Social Function domains was optimal for showing differences from control