Purpose: To investigate in silico the drug-like properties of alkaloids (arecoline, arecaidine, guvacine,
guvacoline, isoguvacine, arecolidine and homoarecoline) obtained from the fruits of
Areca catechu
L
(areca nut).
Methods: All chemical structures were re-drawn using Chemdraw Ultra 11.0. Furthermore, software
including Bio-Loom for Windows - version 1.5, Molinspiration Property Calculator and ACD/I-LAB
service were used to predict the drug-like properties of the alkaloids, including relative molecular mass
(MW), partition coefficient log P (cLog P), number of hydrogen bond donors (HBD), number of hydrogen
bond acceptors (HBA), topological polar surface area (TPSA), number of rotatable bonds (NROTB),
pKa, and aqueous solubility at a given pH (LogS). In addition, Lipinski’s rule was used to evaluate druglike
properties.
Results: From our research, MWs of the seven compounds were all < 500. HBD and cLog P values of
the seven compounds were all < 5, and HBA values were all < 10. In addition, TPSA value of each
compound was < 60 Å
2, and NROTB value was < 10. Besides, pKa values of the seven alkaloids were
> 7.5; furthermore, they possess good solubility at pH 1.0, 5.0, and 7.0.
Conclusion: All the seven alkaloids possess good drug-like properties, and demonstrated good oral
absorption and bioavailability. The results also suggest that these compounds can be further developed
into new oral drugs for treating certain diseases.
