{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T18:46:55Z","timestamp":1791830815686,"version":"4.3.4"},"reference-count":69,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2021,11,20]],"date-time":"2021-11-20T00:00:00Z","timestamp":1637366400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"the Ministry of Science and Technology (MOST), Government of Bangladesh","award":["Grant Number Phy\u2019s-530, dated: 08-12-2020"],"award-info":[{"award-number":["Grant Number Phy\u2019s-530, dated: 08-12-2020"]}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["Grant Number 19K06239"],"award-info":[{"award-number":["Grant Number 19K06239"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of methyl \u03b2-D-galactopyranoside (MGP, 1) analogs were selectively acylated with cinnamoyl chloride in anhydrous N,N-dimethylformamide\/triethylamine to yield 6-O-substitution products, which was subsequently converted into 2,3,4-tri-O-acyl analogs with different acyl halides. Analysis of the physicochemical, elemental, and spectroscopic data of these analogs revealed their chemical structures. In vitro antimicrobial testing against five bacteria and two fungi and the prediction of activity spectra for substances (PASS) showed promising antifungal functionality comparing to their antibacterial activities. Minimum inhibition concentration (MIC) and minimum bactericidal concentration (MBC) tests were conducted for four compounds (4, 5, 6, and 9) based on their activity. MTT assay showed low antiproliferative activity of compound 9 against Ehrlich\u2019s ascites carcinoma (EAC) cells with an IC50 value of 2961.06 \u00b5g\/mL. Density functional theory (DFT) was used to calculate the thermodynamic and physicochemical properties whereas molecular docking identified potential inhibitors of the SARS-CoV-2 main protease (6Y84). A 150-ns molecular dynamics simulation study revealed the stable conformation and binding patterns in a stimulating environment. In-silico ADMET study suggested all the designed molecules to be non-carcinogenic, with low aquatic and non-aquatic toxicity. In summary, all these antimicrobial, anticancer and in silico studies revealed that newly synthesized MGP analogs possess promising antiviral activity, to serve as a therapeutic target for COVID-19.<\/jats:p>","DOI":"10.3390\/molecules26227016","type":"journal-article","created":{"date-parts":[[2021,11,21]],"date-time":"2021-11-21T21:00:50Z","timestamp":1637528450000},"page":"7016","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":58,"title":["Synthesis, Antimicrobial, Anticancer, PASS, Molecular Docking, Molecular Dynamic Simulations &amp; Pharmacokinetic Predictions of Some Methyl \u03b2-D-Galactopyranoside Analogs"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3056-458X","authenticated-orcid":false,"given":"Md. Ruhul","family":"Amin","sequence":"first","affiliation":[{"name":"Laboratory of Carbohydrate and Nucleoside Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Farhana","family":"Yasmin","sequence":"additional","affiliation":[{"name":"Laboratory of Carbohydrate and Nucleoside Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohammed Anowar","family":"Hosen","sequence":"additional","affiliation":[{"name":"Laboratory of Carbohydrate and Nucleoside Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9541-2459","authenticated-orcid":false,"given":"Sujan","family":"Dey","sequence":"additional","affiliation":[{"name":"Department of Microbiology, Faculty of Biological Science, University of Chittagong, Chittagong 4331, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1604-8626","authenticated-orcid":false,"given":"Shafi","family":"Mahmud","sequence":"additional","affiliation":[{"name":"Microbiology Laboratory, Department of Genetic Engineering and Biotechnology, University of Rajshahi, Rajshahi 6205, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5610-4763","authenticated-orcid":false,"given":"Md. Abu","family":"Saleh","sequence":"additional","affiliation":[{"name":"Microbiology Laboratory, Department of Genetic Engineering and Biotechnology, University of Rajshahi, Rajshahi 6205, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3188-2272","authenticated-orcid":false,"given":"Talha Bin","family":"Emran","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, BGC Trust University Bangladesh, Chittagong 4381, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4715-9022","authenticated-orcid":false,"given":"Imtiaj","family":"Hasan","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Molecular Biology, Faculty of Science, University of Rajshahi, Rajshahi 6205, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6408-9620","authenticated-orcid":false,"given":"Yuki","family":"Fujii","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, Nagasaki International University, 2825-7, Huis Ten Bosch-cho, Sasebo, Nagasaki 859-3298, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masao","family":"Yamada","sequence":"additional","affiliation":[{"name":"School of Sciences, Yokohama City University, 22-2, Seto, Kanazawa-ku, Yokohama 236-0027, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2782-6158","authenticated-orcid":false,"given":"Yasuhiro","family":"Ozeki","sequence":"additional","affiliation":[{"name":"School of Sciences, Yokohama City University, 22-2, Seto, Kanazawa-ku, Yokohama 236-0027, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7964-9117","authenticated-orcid":false,"given":"Sarkar Mohammad Abe","family":"Kawsar","sequence":"additional","affiliation":[{"name":"Laboratory of Carbohydrate and Nucleoside Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong 4331, Bangladesh"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,11,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2357","DOI":"10.1126\/science.1059820","article-title":"Chemical glycobiology","volume":"291","author":"Bertozzi","year":"2001","journal-title":"Science"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"371","DOI":"10.1016\/S0076-6879(06)16024-3","article-title":"Cell type-specific roles of carbohydrates in tumor metastasis","volume":"416","author":"Chen","year":"2006","journal-title":"Meth. Enzymol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1093\/glycob\/3.2.97","article-title":"Biological roles of oligosaccharides: All of the theories are correct","volume":"3","author":"Varki","year":"1993","journal-title":"Glycobiology"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1046","DOI":"10.1038\/nature05819","article-title":"Synthesis and medical applications of oligosaccharides","volume":"446","author":"Seeberger","year":"2007","journal-title":"Nature"},{"key":"ref_5","first-page":"211","article-title":"Evaluation of the antimicrobial activity and cytotoxic effect of some uridine derivatives","volume":"12","author":"Kawsar","year":"2018","journal-title":"Int. J. Biosci."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"232","DOI":"10.4236\/ijoc.2015.54023","article-title":"Chemically modified uridine molecules incorporating acyl residues to enhance antibacterial and cytotoxic activities","volume":"5","author":"Kawsar","year":"2015","journal-title":"Int. J. Org. Chem."},{"key":"ref_7","first-page":"83","article-title":"Simple and rapid synthesis of some nucleoside derivatives: Structural and spectral characterization","volume":"5","author":"Shagir","year":"2016","journal-title":"Curr. Chem. Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"465","DOI":"10.17516\/1998-2836-0199","article-title":"Ribose moieties acylation and characterization of some cytidine analogs","volume":"13","author":"Rana","year":"2020","journal-title":"J. Sib. Fed. Univ. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"23","DOI":"10.3897\/pharmacia.68.e56543","article-title":"Synthesis of new series of pyrimidine nucleoside derivatives bearing the acyl moieties as potential antimicrobial agents","volume":"68","author":"Bulbul","year":"2021","journal-title":"Pharmacia"},{"key":"ref_10","first-page":"7","article-title":"An efficient approach to the synthesis of thymidine derivatives containing various acyl groups: Characterization and antibacterial activities","volume":"56","author":"Arifuzzaman","year":"2018","journal-title":"ACTA Pharm. Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"6","DOI":"10.2478\/auoc-2021-0002","article-title":"Synthesis, characterization, synergistic antimicrobial properties and molecular docking of sugar modified uridine derivatives","volume":"32","author":"Maowa","year":"2021","journal-title":"Ovidius. Univ. Ann. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"256","DOI":"10.29356\/jmcs.v65i2.1464","article-title":"Synthesis, characterization, and molecular docking against a receptor protein FimH of Escherichia coli (4XO8) of thymidine derivatives","volume":"65","author":"Alam","year":"2021","journal-title":"J. Mex. Chem. Soc."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s40203-021-00102-0","article-title":"In silico DFT study, molecular docking, and ADMET predictions of cytidine analogs with antimicrobial and anticancer properties","volume":"9","author":"Rana","year":"2021","journal-title":"Silico Pharmacol."},{"key":"ref_14","first-page":"171","article-title":"Bromobenzoylation of methyl \u03b1-D-mannopyranoside: Synthesis and spectral characterization","volume":"14","author":"Farhana","year":"2021","journal-title":"J. Sib. Fed. Univ. Chem."},{"key":"ref_15","first-page":"47","article-title":"Microbial efficacy and two step synthesis of uridine derivatives with spectral characterization","volume":"57","author":"Devi","year":"2019","journal-title":"ACTA Pharm. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"114","DOI":"10.9734\/bpi\/cacb\/v6\/8670D","article-title":"Synthesis, Antibacterial and cytotoxicity assessment of modified uridine molecules","volume":"6","author":"Alam","year":"2021","journal-title":"Curr. Adv. Chem. Biochem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"5206","DOI":"10.4067\/S0717-97072021000205206","article-title":"Computational investigation of methyl \u03b1-D-glucopyranoside derivatives as inhibitor against bacteria, fungi and COVID-19 (SARS-2)","volume":"66","author":"Kawsar","year":"2021","journal-title":"J. Chil. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"153","DOI":"10.15671\/hjbc.622038","article-title":"Novel methyl 4,6-O-benzylidene-\u03b1-D-glucopyranoside derivatives: Synthesis, structural characterization and evaluation of antibacterial activities","volume":"47","author":"Mirajul","year":"2019","journal-title":"Hacettepe J. Biol. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3797\/scipharm.1308-03","article-title":"Regioselective synthesis, characterization and antimicrobial activities of some new monosaccharide derivatives","volume":"82","author":"Kawsar","year":"2014","journal-title":"Sci. Pharm."},{"key":"ref_20","first-page":"125","article-title":"Synthesis, spectroscopic characterization and in vitro antibacterial screening of some D-glucose derivatives","volume":"8","author":"Kawsar","year":"2013","journal-title":"Int. J. Pure Appl. Chem."},{"key":"ref_21","first-page":"299","article-title":"Evaluation of MIC, MBC, MFC and anticancer activities of acylated methyl \u03b2-D-galactopyranoside esters","volume":"16","author":"Misbah","year":"2020","journal-title":"Int. J. Biosci."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"69","DOI":"10.5582\/bst.2020.01020","article-title":"Drug treatment options for the 2019-new coronavirus (2019-nCoV)","volume":"14","author":"Lu","year":"2020","journal-title":"Biosci. Trends"},{"key":"ref_23","first-page":"452","article-title":"Thermochemical, DFT, molecular docking and pharmacokinetic studies of methyl \u03b2-D-galactopyranoside esters","volume":"4","author":"Kawsar","year":"2020","journal-title":"J. Comput. Chem. Mol. Model."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1093\/clinchem\/hvaa080","article-title":"The SARS-CoV-2 outbreak: Diagnosis, infection prevention, and public perception","volume":"66","author":"Wang","year":"2020","journal-title":"Clin. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1126\/science.abb3405","article-title":"Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved a-ketoamide inhibitors","volume":"368","author":"Zhang","year":"2020","journal-title":"Science"},{"key":"ref_26","first-page":"385","article-title":"Pharmacokinetics and molecular docking studies of uridine derivatives as SARS- COV-2 Mpro inhibitors","volume":"9","author":"Maowa","year":"2021","journal-title":"Phys. Chem. Res."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"477","DOI":"10.35812\/CelluloseChemTechnol.2021.55.44","article-title":"Monosaccharide derivatives: Synthesis, antimicrobial, PASS, antiviral, and molecular docking studies against sars-cov-2 mpro inhibitors","volume":"55","author":"Farhana","year":"2021","journal-title":"J. Cellul. Chem. Technol."},{"key":"ref_28","first-page":"88","article-title":"Thermochemical, DFT study, physicochemical, molecular docking and ADMET predictions of some modified uridine derivatives","volume":"8","author":"Bulbul","year":"2021","journal-title":"Int. J. New Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"59","DOI":"10.33435\/tcandtc.718807","article-title":"An optimization and pharmacokinetic studies of some thymidine derivatives","volume":"4","author":"Kawsar","year":"2020","journal-title":"Turk. Comp. Theor. Chem."},{"key":"ref_30","first-page":"66","article-title":"Antibacterial and mycelial growth inhibition of some acylated derivatives of D-glucopyranoside","volume":"2","author":"Kawsar","year":"2012","journal-title":"Int. J. Biosci."},{"key":"ref_31","first-page":"13","article-title":"Synthesis and antibacterial activities of some uridine derivatives","volume":"22","author":"Kabir","year":"1998","journal-title":"Chittagong Univ. J. Sci."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2419","DOI":"10.1021\/cr00023a005","article-title":"Estimation of heats of formation of organic compounds by additivity methods","volume":"93","author":"Cohen","year":"1993","journal-title":"Chem. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"641","DOI":"10.1002\/jps.2600710611","article-title":"Use of dipole moment as a parameter in drug-receptor interaction and quantitative structure-activity relationship studies","volume":"71","author":"Lien","year":"1982","journal-title":"J. Pharm. Sci."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1016\/j.saa.2013.10.042","article-title":"Quantum chemical studies, natural bond orbital analysis and thermodynamic function of 2,5-di-chlorophenylisocyanate","volume":"120","author":"Saravanan","year":"2014","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"27","DOI":"10.4137\/DTI.S12519","article-title":"P-glycoprotein inhibition for optimal drug delivery","volume":"7","author":"Amin","year":"2013","journal-title":"Drug Target Insight"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1002\/9780470125793.ch7","article-title":"Molecular electrostatic potentials and chemical reactivity","volume":"2","author":"Politzer","year":"1991","journal-title":"Rev. Comput. Chem."},{"key":"ref_37","unstructured":"Politzer, P., and Truhlar, D.G. (2013). Chemical Applications of Atomic and Molecular Electrostatic Potentials: Reactivity, Structure, Scattering, and Energetics of Organic, Inorganic, and Biological Systems, Springer Science & Business Media."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1021\/ja0047368","article-title":"The weak hydrogen bond in structural chemistry and biology","volume":"123","author":"Perlstein","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.jgg.2020.02.001","article-title":"Potential inhibitors against 2019-nCoV coronavirus M protease from clinically approved medicines","volume":"7","author":"Liu","year":"2020","journal-title":"J. Genet. Genom."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"4066","DOI":"10.1021\/acs.jmedchem.5b00104","article-title":"pkCSM: Predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures","volume":"58","author":"Pires","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1007\/978-1-4684-7529-6_9","article-title":"The effects of aliphatic alcohols on the biophysical and biochemical correlates of membrane function","volume":"56","author":"Hunt","year":"1975","journal-title":"Adv. Exp. Med. Biol."},{"key":"ref_42","unstructured":"Clinical and Laboratory Standards Institute (CLSI) (2013). Performance Standards for Antimicrobial Disk Susceptibility Tests, Clinical and Laboratory Standards Institute (CLSI). [23rd ed.]. Informational Supplement M100-S23."},{"key":"ref_43","first-page":"1","article-title":"Synthesis of some new derivatives of D-mannose","volume":"29","author":"Kabir","year":"2005","journal-title":"Chittagong Univ. J. Sci."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"122","DOI":"10.56431\/p-v4hx32","article-title":"Infrared, 1 H-NMR Spectral Studies of some Methyl 6-O-Myristoyl-\u03b1-DGlucopyranoside Derivatives: Assessment of Antimicrobial Effects. Int","volume":"58","author":"Kawsar","year":"2015","journal-title":"Lett. Chem. Phys. Astron."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"952","DOI":"10.1016\/j.ijbiomac.2017.04.109","article-title":"Antitumor properties of a methyl-\u03b2-d-galactopyranoside specific lectin from Kaempferia rotunda against Ehrlich ascites carcinoma cells","volume":"102","author":"Ahmed","year":"2017","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_46","first-page":"1035","article-title":"GC-MS analysis and pass-assisted prediction of biological activity spectra of extract of Phomopsis sp. isolated from Andrographis paniculata","volume":"4","author":"Kumaresan","year":"2015","journal-title":"World J. Pharm. Res."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"159","DOI":"10.37358\/RC.21.3.8446","article-title":"Thermochemical, PASS, Molecular Docking, Drug-Likeness and In Silico ADMET Prediction of Cytidine Derivatives Against HIV-1 Reverse Transcriptase","volume":"72","author":"Kawsar","year":"2021","journal-title":"Rev. Chim."},{"key":"ref_48","unstructured":"Gaussian, R.A., Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., and Mennucci, B. (2009). Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry, Gaussian, Inc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","article-title":"Density-functional exchange-energy approximation with correct asymptotic behaviour","volume":"38","author":"Becke","year":"1988","journal-title":"Phys. Rev. A"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"8440","DOI":"10.1073\/pnas.83.22.8440","article-title":"Absolute electronegativity and hardness correlated with molecular orbital theory","volume":"83","author":"Pearson","year":"1986","journal-title":"Proc. Nat. Acad. Sci. USA"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1093\/nar\/28.1.235","article-title":"The protein data bank","volume":"28","author":"Berman","year":"2000","journal-title":"Nucleic Acids Res."},{"key":"ref_53","unstructured":"Delano, W.L. (2002). The PyMOL Molecular Graphics System, De-Lano Scientific. Available online: http:\/\/www.pymol.org."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2714","DOI":"10.1002\/elps.1150181505","article-title":"SWISS-MODEL and the Swiss-Pdb Viewer: An environment for comparative protein modeling","volume":"18","author":"Guex","year":"1997","journal-title":"Electrophoresis"},{"key":"ref_55","unstructured":"Hempel, J.E., Williams, C.H., and Hong, C.C. (2015). Small-molecule library screening by docking with PyRx. Chemical Biology: Methods and Protocols, Springer."},{"key":"ref_56","unstructured":"(2017). 56. Version ADS 4.0, Accelrys."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3099","DOI":"10.1021\/ci300367a","article-title":"admetSAR: A comprehensive source and free tool for assessment of chemical ADMET properties","volume":"52","author":"Cheng","year":"2012","journal-title":"J. Chem. Inf. Mod."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0169-409X(00)00129-0","article-title":"Experimental and computational approaches to estimate solubility and permeability in drug discovery and development","volume":"46","author":"Lipinski","year":"2001","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1007\/978-1-4939-7366-8_4","article-title":"YASARA: A tool to obtain structural guidance in biocatalytic investigations","volume":"1685","author":"Land","year":"2018","journal-title":"Methods Mol. Biol."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1157","DOI":"10.1002\/jcc.20035","article-title":"Development and testing of a general Amber force field","volume":"25","author":"Wang","year":"2004","journal-title":"J. Comput. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"174501","DOI":"10.1063\/1.4872239","article-title":"Structure and dynamics of TIP3P, TIP4P, and TIP5P water near smooth and atomistic walls of different hydroaffinity","volume":"140","author":"Harrach","year":"2014","journal-title":"J. Chem. Phys."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"996","DOI":"10.1002\/jcc.23899","article-title":"New ways to boost molecular dynamics simulations","volume":"36","author":"Krieger","year":"2015","journal-title":"J. Comput. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1016\/j.jmgm.2006.02.009","article-title":"Fast empirical pKa prediction by Ewald summation","volume":"25","author":"Krieger","year":"2006","journal-title":"J. Mol. Graph. Model."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"8577","DOI":"10.1063\/1.470117","article-title":"A smooth particle mesh Ewald method","volume":"103","author":"Essmann","year":"1995","journal-title":"J. Chem. Phys."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"2371","DOI":"10.1021\/ct900275y","article-title":"An implementation of the smooth particle mesh Ewald method on GPU hardware","volume":"5","author":"Harvey","year":"2009","journal-title":"J. Chem. Theory Comput."},{"key":"ref_66","doi-asserted-by":"crossref","unstructured":"Uddin, Z., Paul, A., Rakib, A., Sami, S.A., Mahmud, S., Rana, S., Hossain, S., Tareq, M.A., Dutta, M., and Emran, T. (2021). Chemical profiles and pharmacological properties with in silico studies on elatostema papillosum wedd. Molecules, 26.","DOI":"10.3390\/molecules26040809"},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Mahmud, S., Paul, G.K., Afroze, M., Islam, S., Gupt, S.B.R., Razu, M.H., Biswas, S., Zaman, S., Uddin, M.S., and Khan, M. (2021). Efficacy of phytochemicals derived from avicennia officinalis for the management of covid-19: A combined in silico and biochemical study. Molecules, 26.","DOI":"10.3390\/molecules26082210"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"18103","DOI":"10.1039\/D1RA02885E","article-title":"Immunoinformatics-guided design of a multi-epitope vaccine based on the structural proteins of severe acute respiratory syndrome coronavirus 2","volume":"11","author":"Obaidullah","year":"2021","journal-title":"RSC Adv."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"383","DOI":"10.3389\/fmolb.2021.628585","article-title":"Prospective Role of Peptide-Based Antiviral Therapy Against the Main Protease of SARS-CoV-2","volume":"8","author":"Mahmud","year":"2021","journal-title":"Front. Mol. Biosci."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/22\/7016\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:33:17Z","timestamp":1760167997000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/22\/7016"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,20]]},"references-count":69,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2021,11]]}},"alternative-id":["molecules26227016"],"URL":"https:\/\/doi.org\/10.3390\/molecules26227016","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,20]]}}}