Structure, spectra and bioactivity of pentyl ester of chlorogenic acid: DFT study

The pentyl ester of chlorogenic acid (C₂₁H₂₈O₉) is reportedly a new bioactive biomaterial isolated from the leaves of the Anthocephalus chinensis plant, whose electronic structure and spectral properties are yet to be reported. In this view, the optimized geometry of the titled compound has been modeled using DFT-B3LYP/6-31+G(d,p) methods for the theoretical investigation of the spectroscopic data and electronic structure properties implementing the density functional theory (DFT) approach. The proton (¹H) and carbon-13 (¹³C) nuclear magnetic resonance chemical shifts have also been calculated and compared with experimental values, which reveal a good agreement. A molecular docking study of the titled molecule has also been performed for the prediction of its bioactivity in which its three-dimensional shape at the equilibrium geometry has been exploited as a ligand input to interact with 1hsg and 1gcn protein receptors, which result in the final values of the free energy of binding to be −5·70 and −2·06 kcal/mol, respectively, which imply that the titled molecule may be a good natural anti-immunodeficiency and antidiabetic agent. The outcome of the present study may be useful in developing a natural drug agent and identifying the other novel structures for synthesizing the alternative drugs.