{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T20:21:21Z","timestamp":1788898881391,"version":"build-2803163510"},"reference-count":69,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T00:00:00Z","timestamp":1767830400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Science Committee of the Ministry of Science and Higher Education of the Republic of Kazakhstan","award":["IRN AP23487966"],"award-info":[{"award-number":["IRN AP23487966"]}]},{"DOI":"10.13039\/501100012190","name":"Ministry of Science and Higher Education of the Russian Federation","doi-asserted-by":"crossref","award":["FWUR-2024-0040"],"award-info":[{"award-number":["FWUR-2024-0040"]}],"id":[{"id":"10.13039\/501100012190","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A promising direction for the creation of new biologically active derivatives of the alkaloid lupinine is the synthesis of \u201chybrid molecules\u201d that combine a fragment of the alkaloid and the pharmacophore of 1,2,3-triazole in their structure. From a biological perspective, this work presents the first X-ray diffraction study of a single crystal of (1S,9aR)-1-({4-[4-(Benzyloxy)-3-methoxyphenyl]-1H-1,2,3-triazol-1-yl}methyl)octahydro-2H-quinolizine, a new, recently synthesized 1,2,3-triazole derivative of lupinine. A comparison of theoretically predicted and experimentally observed structural parameters was carried out. The FTIR spectroscopy study and vibrational properties calculations allowed us to interpret the FTIR absorption spectrum and localize specific vibrational modes in quinolizidine, 1,2,3-triazole, and benzene rings. Such information can be fruitful for further characterization of the synthesis process and products. The molecular docking of the compound was performed. It was shown that the studied molecules are capable of interacting with the Mpro binding site via non-covalent and hydrophobic interactions with subsites S3 (Met165, Glu166, Leu167, Pro168) and S5 (Gln189, Thr190, Gln192), which ensure the stabilization of the Mpro substrate. Blocking of the active site of the enzyme in the region of the oxyanion hole does not occur, but stable stacking interactions with the \u03c0-system of one of the catalytic amino acids, His41, are observed.<\/jats:p>","DOI":"10.3390\/molecules31020218","type":"journal-article","created":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T14:32:38Z","timestamp":1767882758000},"page":"218","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Study of Structural, Vibrational, and Molecular Docking Properties of (1S,9aR)-1-({4-[4-(Benzyloxy)-3-methoxyphenyl]-1H-1,2,3-triazol-1-yl}methyl)octahydro-2H-quinolizine"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0245-022X","authenticated-orcid":false,"given":"Dastan","family":"Turdybekov","sequence":"first","affiliation":[{"name":"Department of Physics, Abylkas Saginov Karaganda Technical University, Karaganda 100027, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0978-5663","authenticated-orcid":false,"given":"Zhangeldy","family":"Nurmaganbetov","sequence":"additional","affiliation":[{"name":"Laboratory of Synthesis of Biologically Active Substances, Institute of Organic Synthesis and Coal Chemistry, Karaganda 100008, Kazakhstan"},{"name":"School of Pharmacy, Karaganda Medical University, Karaganda 100012, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Almagul","family":"Makhmutova","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Karaganda Medical University, Karaganda 100012, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1795-9256","authenticated-orcid":false,"given":"Dmitry","family":"Baev","sequence":"additional","affiliation":[{"name":"Synchrotron Radiation Facility\u2014Siberian Circular Photon Source \u201cSKlF\u201d Boreskov Institute of Catalysis of Siberian Branch of the Russian Academy of Sciences , Koltsovo 630559, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4128-7293","authenticated-orcid":false,"given":"Yury","family":"Gatilov","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dmitrii","family":"Pankin","sequence":"additional","affiliation":[{"name":"Center for Optical and Laser Materials Research, St. Petersburg State University, Ulianovskaya 5, St. Petersburg 198504, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4292-1989","authenticated-orcid":false,"given":"Mikhail","family":"Smirnov","sequence":"additional","affiliation":[{"name":"Faculty of Physics, St. Petersburg State University, Universitetskaya Nab. 7\/9, St. Petersburg 199034, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3575-9888","authenticated-orcid":false,"given":"Pernesh","family":"Bekisheva","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Karaganda Medical University, Karaganda 100012, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kymbat","family":"Kopbalina","sequence":"additional","affiliation":[{"name":"Department of Physics, Abylkas Saginov Karaganda Technical University, Karaganda 100027, Kazakhstan"},{"name":"Department of Physics and Nanotechnology, E.A. Buketov Karaganda National Research University, Universitetskaya 28, Karaganda 100024, Kazakhstan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,1,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5644","DOI":"10.1021\/jm050408c","article-title":"4-Aryl-1,2,3-triazole: A novel template for a reversible methionine aminopeptidase 2 inhibitor, optimized to inhibit angiogenesis in vivo","volume":"48","author":"Kallander","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"4829","DOI":"10.1016\/j.bmc.2008.03.049","article-title":"1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin","volume":"16","author":"Odlo","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1016\/j.bmcl.2009.10.127","article-title":"Synthesis and antitumor activity of novel 2\u2032,3\u2032-dideoxy-2\u2032,3\u2032-diethanethionucleosides bearing 1,2,3-triazole residues","volume":"20","author":"Yu","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"6157","DOI":"10.1016\/j.bmc.2015.07.069","article-title":"Synthesis of 1,2-benzisoxazole tethered 1,2,3-triazoles that exhibit anticancer activity in acute myeloid leukemia cell lines by inhibiting histone deacetylases, and inducing p21 and tubulin acetylation","volume":"23","author":"Ashwini","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3389","DOI":"10.1021\/jm1000979","article-title":"N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamides as a new scaffold that provides rapid access to antimicrotubule agents: Synthesis and evaluation of antiproliferative activity against select cancer cell lines","volume":"53","author":"Stefely","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5225","DOI":"10.1016\/j.bmcl.2010.06.141","article-title":"An efficient one-pot synthesis of heterocycle-fused 1,2,3-triazole derivatives as anti-cancer agents","volume":"20","author":"Yan","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.bioorg.2015.01.003","article-title":"Synthesis and biological evaluation of phenyl-1H-1,2,3-triazole derivatives as anti-inflammatory agents","volume":"59","author":"Kim","year":"2015","journal-title":"Bioorg. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.bioorg.2018.07.029","article-title":"1,2,3-triazole tethered indole-3-glyoxamide derivatives as multiple inhibitors of 5-LOX, COX-2 & tubulin: Their anti-proliferative & anti-inflammatory activity","volume":"81","author":"Naaz","year":"2018","journal-title":"Bioorg. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1017","DOI":"10.1007\/s11030-011-9319-0","article-title":"Targeting tuberculosis through a small focused library of 1,2,3-triazoles","volume":"15","author":"Labadie","year":"2011","journal-title":"Mol. Divers."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5988","DOI":"10.1021\/jm2003624","article-title":"Novel 1,2,3-triazole derivatives for use against Mycobacterium tuberculosis H37Rv (ATCC 27294) strain","volume":"54","author":"Boechat","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3911","DOI":"10.1021\/jm300125e","article-title":"Design, synthesis, and structure-activity correlations of novel dibenzo[b,d]furan, dibenzo[b,d]thiophene and N-methylcarbazole clubbed 1,2,3-triazoles as potent inhibitors of Mycobacterium tuberculosis","volume":"55","author":"Patpi","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4573","DOI":"10.1073\/pnas.0909133107","article-title":"Targeting mycobacterium protein tyrosine phosphatase B for antituberculosis agents","volume":"107","author":"Zhou","year":"2010","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1016\/j.ejmech.2016.02.041","article-title":"Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities","volume":"113","author":"Kant","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1016\/j.ejmech.2016.07.024","article-title":"Design, synthesis, anticancer, antimicrobial activities and molecular docking studies of theophylline containing acetylenes and theophylline containing 1,2,3-triazoles with variant nucleoside derivatives","volume":"123","author":"Ruddarraju","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1016\/j.ejmech.2014.07.042","article-title":"Ultrasound-assisted synthesis of novel 1,2,3-triazole coupled diaryl sulfone moieties by the CuAAC reaction, and biological evaluation of them as antioxidant and antimicrobial agents","volume":"84","author":"Mady","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1016\/j.bmcl.2013.11.013","article-title":"1,2,3-Triazole-derived naphthalimides as a novel type of potential antimicrobial agents: Synthesis, antimicrobial activity, interaction with calf thymus DNA and human serum albumin","volume":"24","author":"Lv","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_17","first-page":"2307","article-title":"Synthesis, structure and biological activity of (1S,9aR)-1H-1,2,3-triazol-1-yl)methyl)octahydro-1H-quinolizine derivatives of lupinine","volume":"77","author":"Nurkenov","year":"2022","journal-title":"Arch. Razi Inst."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2144","DOI":"10.1021\/jm2013503","article-title":"Design, synthesis, and In Vitro biological evaluation of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein","volume":"55","author":"Cheng","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Nurmaganbetov, Z.S., Nurkenov, O.A., Khlebnikov, A.I., Fazylov, S.D., Seidakhmetova, R.B., Tukhmetova, Z.K., Takibayeva, A.T., Khabdolda, G., Rakhimberlinova, Z.B., and Kaldybayeva, A.K. (2024). Antiviral Activity of (1S,9aR)-1-[(1,2,3-Triazol-1-yl)methyl]octahydro-1H-quinolizines from the Alkaloid Lupinine. Molecules, 29.","DOI":"10.3390\/molecules29235742"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"161","DOI":"10.3851\/IMP2564","article-title":"Antivirally active ribavirin analogues 4,5-disubstituted 1,2,3-triazole nucleosides: Biological evaluation against certain respiratory viruses and computational modelling","volume":"23","author":"Krajczyk","year":"2014","journal-title":"Antivir. Chem. Chemother."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1501","DOI":"10.1007\/s00044-013-0762-6","article-title":"Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs","volume":"23","author":"Pinheiro","year":"2014","journal-title":"Med. Chem. Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"260","DOI":"10.3998\/ark.5550190.0010.725","article-title":"Synthesis of novel alkaloid derivatives from vinyl ether of lupinine and pH-addends","volume":"2009","author":"Gusarova","year":"2009","journal-title":"Arkivoc"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4668","DOI":"10.1021\/jm100298d","article-title":"Novel quinolizidinyl derivatives as antiarrhythmic agents: 2. Further investigation","volume":"53","author":"Tasso","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Tasso, B., Mattioli, L.B., Tonelli, M., Boido, V., Chiarini, A., Sparatore, F., and Budriesi, R. (2023). Further quinolizidine derivatives as antiarrhythmic agents\u20143. Molecules, 28.","DOI":"10.20944\/preprints202308.0877.v1"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1823","DOI":"10.1134\/S0022476620110153","article-title":"Synthesis, crystal structure, and stability of N-lupinyl phthalimide conformers","volume":"61","author":"Turdybekov","year":"2020","journal-title":"J. Struct. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"506","DOI":"10.1007\/s10600-019-02726-3","article-title":"Synthesis, structure and properties of new O-acyl derivatives of the lupinine alkaloid","volume":"55","author":"Nurkenov","year":"2019","journal-title":"Chem. Nat. Compd."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"12","DOI":"10.31489\/2022Ch2\/2-22-5","article-title":"Synthesis and structure of 4-substituted (1S,9aR)-1-[(1,2,3-triazol-1-yl)methyl]octahydro-1H-quinolizines of lupinine","volume":"106","author":"Nurmaganbetov","year":"2022","journal-title":"Bull. Univ. Karaganda Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"175","DOI":"10.18321\/ectj1641","article-title":"Synthesis and spatial structure of 3-phenylacrylic acid octahydroquinolizin-1-ylmethyl ester and 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione","volume":"26","author":"Nurmaganbetov","year":"2024","journal-title":"Eurasian Chem.-Technol. J."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Schepetkin, I.A., Nurmaganbetov, Z.S., Fazylov, S.D., Nurkenov, O.A., Khlebnikov, A.I., Seilkhanov, T.M., Kishkentaeva, A.S., Shults, E.E., and Quinn, M.T. (2023). Inhibition of acetylcholinesterase by novel lupinine derivatives. Molecules, 28.","DOI":"10.3390\/molecules28083357"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"911","DOI":"10.1007\/s10593-021-03000-7","article-title":"Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine","volume":"57","author":"Nurmaganbetov","year":"2021","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Kishkentayeva, A., Kopbalina, K., Shaimerdenova, Z., Shults, E., Gatilov, Y., Pankin, D., Smirnov, M., Povolotckaia, A., Turdybekov, D., and Mazhenov, N. (2025). Investigation of N-(2-oxo-2H-chromen-3-carbonyl)cytisine\u2019s Crystal Structure and Optical Properties. Materials, 18.","DOI":"10.3390\/ma18133153"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Kopbalina, K., Pankin, D., Smirnov, M., Ibrayev, N., and Turdybekov, D. (2025). Arrangement of Azidomethyl Group in Lupinine Azide: Structural and Spectroscopic Properties. Molecules, 30.","DOI":"10.3390\/molecules30030582"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"766","DOI":"10.1016\/j.apsb.2020.02.008","article-title":"Analysis of therapeutic targets for SARS-CoV-2 and discovery of potential drugs by computational methods","volume":"10","author":"Wu","year":"2020","journal-title":"Acta Pharm. Sin. B"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1038\/s41594-020-0440-6","article-title":"Structural basis for the inhibition of SARS-CoV-2 main protease by antineoplastic drug carmofur","volume":"27","author":"Jin","year":"2020","journal-title":"Nat. Struct. Mol. Biol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"127377","DOI":"10.1016\/j.bmcl.2020.127377","article-title":"The SARS-CoV-2 main protease as drug target","volume":"30","author":"Ullrich","year":"2020","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1331","DOI":"10.1126\/science.abb4489","article-title":"Structure-based design of antiviral drug candidates targeting the SARS-CoV-2 main protease","volume":"368","author":"Dai","year":"2020","journal-title":"Science"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"116704","DOI":"10.1016\/j.ejmech.2024.116704","article-title":"Covalent small-molecule inhibitors of SARS-CoV-2 Mpro: Insights into their design, classification, biological activity, and binding interactions","volume":"277","author":"Shawky","year":"2024","journal-title":"Eur. J. Med. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1457","DOI":"10.1021\/acsinfecdis.0c00815","article-title":"Challenges for targeting SARS-CoV-2 proteases as a therapeutic strategy for COVID-19","volume":"7","author":"Steuten","year":"2021","journal-title":"ACS Infect. Dis."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Olosunde, A., and Hu, X. (2025). Molecular recognition of SARS-CoV-2 Mpro inhibitors: Insights from cheminformatics and quantum chemistry. Molecules, 30.","DOI":"10.3390\/molecules30102174"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"534","DOI":"10.1021\/jm050540c","article-title":"Novel procedure for modeling ligand\/receptor induced fit effects","volume":"49","author":"Sherman","year":"2006","journal-title":"J. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"6177","DOI":"10.1021\/jm051256o","article-title":"Extra precision Glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein\u2212ligand complexes","volume":"49","author":"Friesner","year":"2006","journal-title":"J. Med. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1002\/prot.10613","article-title":"A hierarchical approach to all-atom protein loop prediction","volume":"55","author":"Jacobson","year":"2004","journal-title":"Proteins Struct. Funct. Genet."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Bowers, K.J., Chow, D.E., Xu, H., Dror, R.O., Eastwood, M.P., Gregersen, B.A., Klepeis, J.L., Kolossvary, I., Moraes, M.A., and Sacerdoti, F.D. (2007). Scalable Algorithms for Molecular Dynamics Simulations on Commodity Clusters, IEEE.","DOI":"10.1145\/1188455.1188544"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.apsb.2023.08.004","article-title":"Medicinal chemistry strategies towards the development of non-covalent SARS-CoV-2 Mpro inhibitors","volume":"14","author":"Song","year":"2024","journal-title":"Acta Pharm. Sin. B"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"e0069722","DOI":"10.1128\/aac.00697-22","article-title":"A randomized Phase 2\/3 study of ensitrelvir, a novel oral SARS-CoV-2 3C-like protease inhibitor, in Japanese patients with mild-to-moderate COVID-19 or asymptomatic SARS-CoV-2 infection: Results of the Phase 2a part","volume":"66","author":"Mukae","year":"2022","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"980","DOI":"10.1107\/S0567740880005080","article-title":"Structure of (\u2212)-lupinine","volume":"36","author":"Koziol","year":"1980","journal-title":"Acta Crystallogr."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"S1","DOI":"10.1039\/p298700000s1","article-title":"Tables of bond lengths determined by X-ray and neutron diffraction","volume":"2","author":"Allen","year":"1987","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"5630","DOI":"10.1021\/j100377a041","article-title":"Ab initio conformational analysis of cyclohexane","volume":"94","author":"Dixon","year":"1990","journal-title":"J. Phys. Chem."},{"key":"ref_49","unstructured":"(SMART and SAINT, Area Detector Control and Integration Software, 2012). SMART and SAINT, Area Detector Control and Integration Software."},{"key":"ref_50","unstructured":"Sheldrick, G.M. (SADABS ver 2018\/3, 2012). SADABS ver 2018\/3."},{"key":"ref_51","unstructured":"(APEX2, Software Suite for Crystallographic Programs, 2009). APEX2, Software Suite for Crystallographic Programs."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystaollogr. Sect. A Found. Crystallogr."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"714","author":"Sheldrick","year":"2015","journal-title":"Acta Crystaollogr. Sect. C Struct. Chem."},{"key":"ref_54","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2025, October 31). Gaussian 09, Revision C.01. Available online: https:\/\/gaussian.com\/glossary\/g09\/."},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Pankin, D., Smirnov, M., Povolotckaia, A., Povolotskiy, A., Borisov, E., Moskovskiy, M., Gulyaev, A., Gerasimenko, S., Aksenov, A., and Litvinov, M. (2022). DFT Modelling of Molecular Structure, Vibrational and UV-Vis Absorption Spectra of T-2 Toxin and 3-Deacetylcalonectrin. Materials, 15.","DOI":"10.3390\/ma15020649"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Gooneie, A., Schuschnigg, S., and Holzer, C. (2017). A Review of Multiscale Computational Methods in Polymeric Materials. Polymers, 9.","DOI":"10.3390\/polym9010016"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density-Functional Thermochemistry. III. The Role of Exact Exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_58","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_59","doi-asserted-by":"crossref","first-page":"650","DOI":"10.1063\/1.438955","article-title":"Self-Consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions","volume":"72","author":"Krishnan","year":"1980","journal-title":"J. Chem. Phys."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"118933","DOI":"10.1016\/j.saa.2020.118933","article-title":"Spectral properties of triphenyltin chloride toxin and its detectivity by SERS: Theory and experiment","volume":"245","author":"Pankin","year":"2021","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"122469","DOI":"10.1016\/j.saa.2023.122469","article-title":"Theoretical modelling of structure, vibrational and UV\u2013vis absorbance spectra of rubrofusarin molecule","volume":"293","author":"Pankin","year":"2023","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Pankin, D., Povolotckaia, A., Smirnov, M., Borisov, E., Gulyaev, A., Dorochov, A., and Moskovskiy, M. (2023). Theoretical investigation of Anhydrofusarubin: Structural and Optical properties. Crystals, 13.","DOI":"10.3390\/cryst13111556"},{"key":"ref_63","doi-asserted-by":"crossref","unstructured":"Povolotckaia, A., Pankin, D., Novikov, V., Borisov, E., Kuznetsov, S., Dorokhov, A., and Moskovskiy, M. (2024). Investigation of Structural and Spectral Peculiarities of Fusarium sp. Indicator Pigment Bostrycoidin. Molecules, 29.","DOI":"10.3390\/molecules29194765"},{"key":"ref_64","unstructured":"(2025, October 31). Schr\u00f6dinger Software, Available online: https:\/\/www.schrodinger.com."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"721","DOI":"10.1007\/s40265-024-02039-y","article-title":"Ensitrelvir Fumaric Acid: First Approval","volume":"84","author":"Syed","year":"2024","journal-title":"Drugs"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1021\/acscentsci.2c01359","article-title":"Development of Highly Potent Noncovalent Inhibitors of SARS-CoV-2 3CLpro","volume":"9","author":"Hou","year":"2023","journal-title":"ACS Cent. Sci."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"114929","DOI":"10.1016\/j.celrep.2024.114929","article-title":"An oral non-covalent non-peptidic inhibitor of SARS-CoV-2 Mpro ameliorates viral replication and pathogenesis in vivo","volume":"43","author":"Zhou","year":"2024","journal-title":"Cell Rep."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2110","DOI":"10.1002\/qua.24481","article-title":"Jaguar: A High-Performance Quantum Chemistry Software Program with Strengths in Life and Materials Sciences","volume":"113","author":"Bochevarov","year":"2013","journal-title":"Int. J. Quantum Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"116","DOI":"10.1021\/acs.jcim.1c00851","article-title":"High-Throughput Virtual Screening and Validation of a SARS-CoV-2 Main Protease Noncovalent Inhibitor","volume":"62","author":"Clyde","year":"2022","journal-title":"J. Chem. Inf. 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