Antibacterial Potential of Trihydroxycyclohexa-2,4-Diene-1- Carboxylic Acid: Insight from DFT, Molecular Docking, and Molecular Dynamic Simulation
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Taylor&Francis online
Abstract
Description
In this study, (z)-5-((3-(2,3-dihydroxyphenyl) acryloyl) oxy)- 1,3,4-trihydroxycyclohexa-
2,4-diene-1-carboxylic acid (chlorogenic acid) was isolated and characterized using UVVisible,
1H NMR and 13C NMR, FT-IR, along with detailed investigation using density
functional theory (DFT), in-silico molecular docking, and molecular dynamics (MD)
simulation. Results from DFT calculation indicates that the titled compound is very
stable with energy gap of 3.7–7.8 for variable functionals, and similarly, the structural
parameters show very close agreement with X-ray data for bond lengths and angles.
The FT-IR spectrum results revealed stretching vibration O–H (3366 cm−1), C=O
(1689 cm−1), C–H (1636, 1606, 1522, and 1442 cm−1), C–O (1192 and 1122 cm−1). The
drug-likeness analyses and ADME studies showed drug-likeness ability and good oral
behavior of the investigated compound as it obeys Lipinski, Ghose, Veber and Egan
rules. Hepatotoxic and immunotoxic activities were indicated for the toxicity/toxicological
endpoints of the studied compound. The molecular docking indicates a binding affinity
of −8.30 and 9.5 kcal/mol for the titled compound, which is higher than the standard
drug. From the molecular dynamic simulation results, chlorogenic-2H14 (complex B)
revealed variations in RMSD values of less than 3Å, indicating that the protein structure
underwent minor conformational changes throughout the simulation. Chlorogenicprotein
complexes had average RGyr values of 3.704 − 4.907Å, which indicates
compaction during the simulation. Therefore, it can be said that the titled compound has
potential to be effective as an agent for cholera management, and the results obtained
can be platform further in-vitro, vivo and clinical trials.
Keywords
QH Natural history, QH301 Biology, QR Microbiology