Chemicals are the essential components of the industry for maneuvering the required need of the living ecosystem. Ionic liquids are a group of promising novel chemicals with potential usefulness toward various industrial applications, although they are not entirely devoid of hazardous outcomes. The present study is an attempt to investigate the chemical attributes of a wide variety of 292 ionic liquids toward their inhibitory potential of acetyl cholinesterase enzyme of electric eel through the development of predictive regression and classification-based quantitative mathematical models in the light of the OECD guidelines. Molecular docking studies have additionally corroborated the results. Hydrophilicity, hydrophobicity, branching, and positively charged N-species were observed to be the major chemical contributors to such toxicity. The docking studies chiefly portrayed the pi-cationic type interaction of the cationic N+ atom with the Phe288, Phe290, and Trp23 residues of the acyl binding pocket to be responsible for enzyme inhibition.