Predictive molecular design is an emerging tool in modern molecular physics and chemistry which heavily relies on the understanding of relationships between key structural and electronic properties. Identifying and explaining correlations between properties necessitates either deep physical understanding or exhaustive data analysis. Herein, we present a comprehensive investigation of the intricate interplay between the HOMO-LUMO gap and dipole polarizability -two central properties in designing molecules with tailored optical properties and intermolecular interactions.