In silico clastogenic activity of dietary phenolic acids

•Study of phenolic acids (benzoic and cinnamic) with pro-oxidant activity.•Performance of a virtual screening using the TOPS-MODE approach.•Determination of structural alerts to identify the clastogenic activity.

Phenolic acids have been reported to exert multiple biological effects, including their activity as pro-oxidants. Structural alerts to identify the clastogenic activity of phenolic acids with pro-oxidant activity were determined in the current study. The described methodology was based on the application of a quantitative structure-activity relationship (QSAR) study. It was developed a virtual screening method based on a clastogenic model using the topological substructural molecular design (TOPS-MODE) approach. The model has presented a suitable probability of good classification for the external prediction data set. Therefore, it was possible to establish the structural criteria for maximal clastogenicity (chromosomal aberrations) of pro-oxidant reported phenolic acids. The two main criteria were represented by the presence of methoxy and/or hydroxyl substitutions on the benzene ring and polarity of these substituents. In summary, the apolar regions of phenolic acid derivatives contributed negatively to the activity, while the polar groups favored it.