Theoretical Investigations on Phytochemicals: Physical Chemistry, FMO, MEP, Lipophilicity, Water Solubility, Drug-likeness, and Bioavailability

Abstract

Naturally-existing chemicals especially phytochemicals have been commonly used for medicinal purposes in terms of both traditional and contemporary respects. Allyl isothiocyanate structure exhibits antimicrobial and anticancer activity, whereas the allitridin, as one of the main components of the garlic, showed antifungal, antitumor, and antioxidant activity. Arabinose and galactose as monosaccharides also play a main role in drug-design research to facilitate drug delivery to target cells and regulate insulin resistance, respectively. Herein, the 3-isothiocyanatoprop-1-ene (Allyl isothiocyanate, AITC), 2,3,4,5-tetrahydroxypentanal (Ar, Arabinose), 1,3-diallyltrisulfane (Allitridin, DATS), 6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol (Galactose, Gal), 6-methyltetrahydro-2H-pyran-2,3,4,5-tetraol (Rhamnose, Rh), and tetrahydro-2H-pyran-2,3,4,5-tetraol (cyclic-Arabinose, C-Ar) agents were investigated by using DFT. The B3LYP/6-311G** level computations were used to optimize the compounds' geometries and then to predict the reactivity indexes of the compounds. Also, lipophilicity and water-solubility features were determined to enlighten the physicochemical characteristics of the compounds. Then, the studied agents' pharmacokinetics were evaluated using the BOILED-Egg and radar graphs. Last, the bioavailability and drug-likeness behaviors were predicted. This trial work will be hoped to provide fundamental electronic and physicochemical insight into the relationship between drug-likeness and electronic structure.