&lt;i&gt;In silico&lt;/i&gt; Assessment of Drug-like Properties of Alkaloids from &lt;i&gt;Areca catechu&lt;/i&gt; L Nut

W Peng,Yj Liu,N Wu,Cj Wu,Xs Huang,Cb Zhao,Mb Hu,Ds Xie

doi:10.4314/tjpr.v14i4.11

Abstract

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 Å2, 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.Keywords: Areca catechu L, Areca nut, Drug-like properties, Alkaloids, Arecoline, Arecaidine, Guvacine, Guvacoline, Isoguvacine, Arecolidine, Homoarecoline, In silico

Highlights

The fruit of Areca catechu L, belonging to Arecaceae family, is an important folk medicine used in China to treat parasitic diseases, digestive disorders, and edema [1,2]
The objective of the present stud was to investigate the drug-like properties of alkaloids of areca nut, namely, arecoline, arecaidine, guvacine, guvacoline, isoguvacine, arecolidine, and homoarecoline using an in silico method
According to our present investigation, the in silico predictive results of drug-like properties of alkaloids from areca nut are shown in Table 1 and Table 2

Summary

Introduction

The fruit of Areca catechu L (areca nut), belonging to Arecaceae family, is an important folk medicine used in China to treat parasitic diseases, digestive disorders, and edema [1,2]. PKa values of the seven alkaloids were > 7.5; 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.

Results

Conclusion