Isothiocyanates (ITCs) are naturally organosulfur molecules derived from glucosinolates. Most of them are present in cruciferous vegetables and are responsible for the plant's sharp taste and act as a defense system. Recently ITCs are considerate an important source of nutritional and medical interest. This study aimed to extract chemical structures containing the isothiocyanate moiety reported in four databases: COCONUT, FooDB, PDB, and DrugBank. As a result of this review, we obtained 154 isothiocyanate-like compounds, which were classified according to their chemical skeleton into seven categories: acyclic (69), cyclic (3), polycyclic (41), aromatic (14), polyaromatic (3), indolic (18) and glycosylated (6) (Figure 1). 14 of 24 were found in Brassica oleracea varieties, according to FooDB. Molinspiration, SwissTargetPrediction, and DataWarrior were used to obtain the physicochemical properties. The results indicated that most ITCs were in a range of 100 to 450 Da of molecular weight, clogP around 1 to 6 and PSA from 40 to 120 Å. Moreover, SwissTargetPrediction, PASSonline, ChEMBL, and Epigenetic Target Profiler were used to predict the activity type and molecular targets of 154 ITCs. In general, the predictions showed activity on macrophage migration inhibitory factor, transient receptor potential cation channel subfamily A member 1, membrane receptors as Serotonin 1b (5-HT1b), and epigenetic targets such as serine-protein kinase ATM and DNA lyase. Also, they can inhibit Cytochrome P450 2E1 and can be an apoptosis agonist. This review has provided insights into the physicochemical properties of 154 isothiocyanates reported in four databases. In general, ITCs could be involved in anti-inflammatory and cancer processes with a potential pharmacological effect.

Isothiocyanates: A recent chemoinformatic study

ACS Fall 2021

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