Conceptual DFT study of the chemical reactivity of four natural products with anti-sickling activity

Abstract

Theoretical reactivity indices based on the conceptual density functional theory were computed to investigate the reactivity of four anti-sickling plant-isolated terpenes: betulinic acid, betulinic acid acetate, friedelan-3-one, and ursolic acid. Herein, global reactivity indices such as the HOMO energy, electronic chemical potential, hardness, and electrophilicity and the local reactivity descriptors like Fukui functions, dual descriptors, and molecular electrostatic potentials for the anti-sickling agents are discussed. The binding energies of water on the most active site are in between -19 and -6 kcal/ mol at B3LYP/6-31G(d). A molecular docking of anti-sickling agents and deoxyhemoglobin including binding energies, hydrogen bond distances and pictorial representation of viable docked poses revealed that betulinic acid and ursolic acid are the most potent molecules with a common binding site.