Casearvestrin A, B, and C secundary metabolites, with a promising anticancer potential, were computationally characterized to reveal susceptible sites to nucleophilic and electrophilic attacks, establishing the types and strength of chemical bonds and non-covalent interactions using the B3LYP/6-311++G(d,p) theory level. The chemical behavior prediction was performed by the analysis of local besides global reactivity indexes based on the analysis of the Fukui functions and the topological analysis of the electronic density according to Bader’s theory. Casearvestrin A is the most reactive molecule since it has less hardness, smallest band gap, a highest number of C-H--O weak interactions, and both type of susceptible sites, nucleophilic and electrophilic. Electrophilic attacks are most favored at oxygen atoms of the carbonyl groups, the hydroxyl group, and the cyclic ether. The length of the R chain, which differentiates this type of metabolites, is related to the number of H--H interactions, which in turn has a relationship with the dipole moment