{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,17]],"date-time":"2026-05-17T05:06:22Z","timestamp":1778994382452,"version":"3.51.4"},"reference-count":53,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T00:00:00Z","timestamp":1778803200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003593","name":"National Council for Scientific and Technological Development","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100002322","name":"Coordination for the Improvement of Higher Education Personnel","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100006181","name":"Bahia State Research Support Foundation","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100006181","id-type":"DOI","asserted-by":"crossref"}]},{"name":"Internal Financial Assistance Program for Publication in Qualified National and International Journals for Postgraduate Studies"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The flavonoids constitute a class of secondary metabolites distributed in plants, occurring in free form (aglycone) or conjugated sugars (glycosides), and are notable for their recognized pharmacological potential. This study investigated flavonoids isolated from the leaves of Erythroxylum rimosum, correlating their chemical structures with biological activities evaluated in vitro assays. The flavonoids did not show significant cytotoxicity in mammalian cells (CC50 &gt; 100 \u03bcM), while flavonoids 4 and 5, glycosylated with six-carbon sugar, inhibited the promastigote forms of L. braziliensis with IC50 of 10.34 \u00b1 0.70 \u03bcM and 10.14 \u00b1 0.50 \u03bcM, respectively. In intracellular infection models, they reduced ~43% of parasitized cells and ~40% of amastigotes. Scanning electron microscopy demonstrated changes in promastigotes, including loss of membrane integrity and flagellum shortening. A molecular docking study with L. mexicana arginase suggested enzyme inhibition as a possible mechanism of action, influenced by sugar chirality. In the antioxidant evaluation, using the DPPH and \u03b2-carotene methods, quercetin showed the best inhibitory concentration value (IC50 = 0.22 \u00b1 0.94 mg\/mL), followed by glycoside 5 (IC50 = 0.42 \u00b1 0.09 mg\/mL). In addition, the flavonoids glycosylated with five-carbon sugar inhibited the acetylcholinesterase enzyme.<\/jats:p>","DOI":"10.3390\/molecules31101669","type":"journal-article","created":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T08:50:12Z","timestamp":1778835012000},"page":"1669","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Structure\u2013Activity Relationship Analysis of Flavonoids Isolated from the Leaves of Erythroxylum rimosum O. E. Schulz"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-9818-2591","authenticated-orcid":false,"given":"Ivana P.","family":"dos Santos","sequence":"first","affiliation":[{"name":"Departamento de Ci\u00eancias da Vida, Universidade Estadual da Bahia, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria Eduarda V.","family":"Costa","sequence":"additional","affiliation":[{"name":"Escola Bahiana de Medicina e Sa\u00fade P\u00fablica, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-6159-2169","authenticated-orcid":false,"given":"Geovana A.","family":"de Oliveira","sequence":"additional","affiliation":[{"name":"Escola Bahiana de Medicina e Sa\u00fade P\u00fablica, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-2743-7847","authenticated-orcid":false,"given":"Francisnaira S.","family":"Santos","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias da Vida, Universidade Estadual da Bahia, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D\u00e9bora O. S.","family":"Vit\u00f3ria","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias da Vida, Universidade Estadual da Bahia, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9808-1691","authenticated-orcid":false,"given":"Robson Almeida","family":"Silva","sequence":"additional","affiliation":[{"name":"Faculdade de Farm\u00e1cia, Universidade Federal da Bahia, Salvador 40170-115, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Janaina M. C.","family":"do Vale","sequence":"additional","affiliation":[{"name":"Faculdade de Farm\u00e1cia, Universidade Federal da Bahia, Salvador 40170-115, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gildeon S.","family":"Marques","sequence":"additional","affiliation":[{"name":"Faculdade de Farm\u00e1cia, Universidade Federal da Bahia, Salvador 40170-115, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ademir Evangelista do","family":"Vale","sequence":"additional","affiliation":[{"name":"Faculdade de Farm\u00e1cia, Universidade Federal da Bahia, Salvador 40170-115, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Milena Botelho Pereira","family":"Soares","sequence":"additional","affiliation":[{"name":"Instituto Gon\u00e7alo Moniz, Salvador 40296-710, Brazil"},{"name":"Instituto SENAI de Inova\u00e7\u00e3o em Sistemas Avan\u00e7ados em Sa\u00fade (CIMATEC ISI SAS), Salvador 41650-010, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8385-5375","authenticated-orcid":false,"given":"Taise de A.","family":"Ara\u00fajo","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias da Vida, Universidade Estadual da Bahia, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7884-2177","authenticated-orcid":false,"given":"Andr\u00e9 Braga","family":"Teles","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias da Vida, Universidade Estadual da Bahia, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elisalva Teixeira","family":"Guimar\u00e3es","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias da Vida, Universidade Estadual da Bahia, Salvador 41150-000, Brazil"},{"name":"Instituto Gon\u00e7alo Moniz, Salvador 40296-710, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Erika Maria de Oliveira","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias da Vida, Universidade Estadual da Bahia, Salvador 41150-000, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2026,5,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Restrepo, D.A., Saenz, E., Jara-Mu\u00f1oz, O.A., Calixto-Bot\u00eda, I.F., Rodr\u00edguez-Su\u00e1rez, S., Zuleta, P., Chavez, B.G., Sanchez, J.A., and D\u2019auria, J.C. (2019). Erythroxylum in focus: An interdisciplinary review of an overlooked genus. Molecules, 24.","DOI":"10.3390\/molecules24203788"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1007\/s13659-022-00338-z","article-title":"Advances in chemistry and bioactivity of the genus Erythroxylum","volume":"12","author":"Lv","year":"2022","journal-title":"Nat. Prod. Bioprospect."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"e44101018282","DOI":"10.33448\/rsd-v10i10.18282","article-title":"Use of medicinal plants: History and relevance","volume":"10","author":"Filho","year":"2021","journal-title":"Res. Soc. Dev."},{"key":"ref_4","first-page":"100893","article-title":"Antioxidant, antibacterial, cytotoxic and thrombolytic activities of flowers of Mirabilis jalapa L: Possible role of phenolics and flavonoids","volume":"14","author":"Rashid","year":"2023","journal-title":"J. Agric. Food Res."},{"key":"ref_5","first-page":"51","article-title":"Antimicrobial activity of flavonoids: A literature review","volume":"4","author":"Kowalski","year":"2020","journal-title":"Interdiscip. J. Health Biol. Sci."},{"key":"ref_6","first-page":"1","article-title":"Medicinal plants: Past history and future perspective","volume":"7","author":"Lorigooini","year":"2017","journal-title":"J. Herbmed Pharmacol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"e532101019013","DOI":"10.33448\/rsd-v10i10.19013","article-title":"Chemical composition and evaluation of antioxidant and anticholinesterase activities of oil from the fruits of Ouratea fieldingiana (Gargner)","volume":"10","author":"Frota","year":"2021","journal-title":"Engl. Res. Soc. Dev."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Mucha, P., Skoczy\u0144ska, A., Ma\u0142ecka, M., Hikisz, P., and Budzisz, E. (2021). Overview of the antioxidant and anti-inflammatory activities of selected plant compounds and their metal ions complexes. Molecules, 26.","DOI":"10.3390\/molecules26164886"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2720","DOI":"10.30574\/wjarr.2025.25.2.0593","article-title":"Leveraging Natural Antioxidants in Disease Prevention: Investigating the Role of Medicinal Herbs in Reducing Oxidative Stress and Chronic Disease","volume":"25","author":"Allison","year":"2025","journal-title":"World J. Adv. Res. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2438069","DOI":"10.1080\/17518253.2024.2438069","article-title":"Phytochemical screening and evaluation of anti-oxidant, anti-inflammatory and anticancer activities of leaves of Vernonia amygdalina, Otostegia integrifolia, and Salvia rosmarinus","volume":"18","author":"Dejene","year":"2025","journal-title":"Green Chem. Lett. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Kurtul, E., Akkol, E.K., A\u011f\u00f6ren, B.K., Yaylac\u0131, B., Ac\u0131kara, \u00d6.B., and Sobarzo-S\u00e1nchez, E. (2025). Phytochemical investigation and assessment of the anti-inflammatory activity of four Heracleum taxa growing in Turkey. Front. Pharmacol., 15.","DOI":"10.3389\/fphar.2024.1494786"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"115027","DOI":"10.1016\/j.intimp.2025.115027","article-title":"Exploring the anti-inflammatory effects of total flavonoids from L. gracile on LPS-induced inflammation: An integrated approach combining network pharmacology, molecular docking, and experimental validation","volume":"161","author":"Li","year":"2025","journal-title":"Int. Immunopharmacol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3233","DOI":"10.2147\/DDDT.S466470","article-title":"Flavonoids and gastric cancer therapy: From signaling pathway to therapeutic significance","volume":"18","author":"Cai","year":"2024","journal-title":"Drug Des. Dev. Ther."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Orioli, R., Belluti, F., Gobbi, S., Rampa, A., and Bisi, A. (2024). Naturally inspired coumarin derivatives in Alzheimer\u2019s disease drug discovery: Latest advances and current challenges. Molecules, 29.","DOI":"10.3390\/molecules29153514"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"77","DOI":"10.58624\/SVOAMB.2025.06.010","article-title":"Phytochemical Profile and Modifying Potential of Erythroxylum rosuliferum OE Schulz (Erythroxylaceae)","volume":"6","author":"Silva","year":"2025","journal-title":"SVOA Microbiol."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Singh, P.K., Gupta, G.S., Kumar, I., Kumar, U., Madheshiya, P., Dwivedi, A., Singh, P., Mishra, A.K., Mishra, S., and Gupta, S. (2025). Therapeutic Potential of Biotoxins and Biotechnological Innovations. Biotoxins: Biotechnological and Therapeutic Applications, Springer Nature.","DOI":"10.1007\/978-3-031-75309-1_16"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"e202400911","DOI":"10.1002\/cbdv.202400911","article-title":"Genus Berberis: A comprehensive and updated review on ethnobotanical uses, phytochemistry and pharmacological activities","volume":"21","author":"Saleem","year":"2024","journal-title":"Chem. Biodivers."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"De-Lima, L.H.D.G., Gomes, M.W.F., Curado, T.S.d.S., Naves, L.M., Marques, S.M., Oliveira, M.S., Ogbu, J.I., Menezes, A.C.S., Vila Verde, G.M., and Fajemiroye, J.O. (2024). Cardiovascular effects of a glycosylated flavonoids-rich leaf extract from Brazilian Erythroxylum campestre: A potential health bio-input. Pharmaceuticals, 17.","DOI":"10.3390\/ph17111456"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3051","DOI":"10.1080\/07391102.2023.2212062","article-title":"Multitargeted molecular docking and dynamics simulation studies of flavonoids and volatile components from the peel of Citrus sinensis L. (Osbeck) against specific tumor protein markers","volume":"42","author":"Sharanya","year":"2024","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"110372","DOI":"10.1016\/j.abb.2025.110372","article-title":"Phytochemical inhibitors of squalene epoxidase: Integrated in silico and in vitro mechanistic insights for targeting cholesterol biosynthesis","volume":"768","author":"Kamel","year":"2025","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_21","first-page":"12","article-title":"Bioactive flavonoids in medicinal plants: Structure, activity and biological fate","volume":"13","author":"Wang","year":"2018","journal-title":"Asian J. Pharm. Sci."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Sl\u00e1mov\u00e1, K., Kape\u0161ov\u00e1, J., and Valentov\u00e1, K. (2018). \u201cSweet flavonoids\u201d: Glycosidase-catalyzed modifications. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19072126"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"5445291","DOI":"10.1155\/2022\/5445291","article-title":"Flavonoids a bioactive compound from medicinal plants and its therapeutic applications","volume":"2022","author":"Roy","year":"2022","journal-title":"BioMed Res. Int."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"105095","DOI":"10.1016\/j.fbio.2024.105095","article-title":"Viola stocksii: A rich source of antioxidant and anti-inflammatory flavonoid glycosides with converged therapeutic potential against SARS-CoV-2 MPro, spike trimer, and surface glycoproteins","volume":"62","author":"Zamir","year":"2024","journal-title":"Food Biosci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"e238111436225","DOI":"10.33448\/rsd-v11i14.36225","article-title":"Antioxidant potential of flavonoids and therapeutic applications","volume":"11","author":"Moraes","year":"2022","journal-title":"Res. Soc. Dev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"5243","DOI":"10.3390\/ijerph18105243","article-title":"Scutellaria baicalensis and their natural flavone compounds as potential medicinal drugs for the treatment of nicotine-induced non-small-cell lung cancer and asthma","volume":"18","author":"Alsharairi","year":"2021","journal-title":"Int. J. Environ. Res. Public Health"},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Dias, M.C., Pinto, D.C.G.A., and Silva, A.M.S. (2021). Plant flavonoids: Chemical characteristics and biological activity. Molecules, 26.","DOI":"10.3390\/molecules26175377"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/j.phytol.2013.02.008","article-title":"A new tropane alkaloid and other constituents of Erythroxylum rimosum (Erythroxylaceae)","volume":"6","author":"Lima","year":"2013","journal-title":"Phytochem. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1016\/j.abb.2013.03.015","article-title":"Crystal structure of arginase from Leishmania mexicana and implications for the inhibition of polyamine biosynthesis in parasitic infections","volume":"535","author":"Ullman","year":"2013","journal-title":"Biochem. Biophys. Arch."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"100603","DOI":"10.1016\/j.phyplu.2024.100603","article-title":"Comparando efeitos antioxidantes e citoprotetores: Glicos\u00eddeo de quercetina vs. aglicona de Ephedra alata","volume":"4","author":"Maaiden","year":"2024","journal-title":"Phytomed. Plus"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1139\/v02-113","article-title":"Ab initio and DFT conformational analysis of selected flavones: 5,7-dihydroxyflavone (chrysin) and 7,8-dihydroxyflavone","volume":"80","author":"Lau","year":"2002","journal-title":"Can. J. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.1007\/s10534-025-00696-4","article-title":"Therapeutic applications of quercetin-metallic complexes: A review","volume":"38","author":"Ramzan","year":"2025","journal-title":"BioMetals"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"100651","DOI":"10.1016\/j.rechem.2022.100651","article-title":"The syntheses of polymethoxy flavonoid glycosides from apigenin and diosmetin and their cytotoxic activities on two human cancer cell lines","volume":"4","author":"Nguyen","year":"2022","journal-title":"Results Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1080\/13880209.2021.1903047","article-title":"Cytotoxic activity of standardized extracts, a fraction, and individual secondary metabolites from fenugreek seeds against SKOV-3, HeLa and MOLT-4 cell lines","volume":"59","author":"Kimel","year":"2021","journal-title":"Pharm. Biol."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Gervazoni, L.F.O., Gon\u00e7alves-Oz\u00f3rio, G., and Almeida-Amaral, E.E. (2018). 2\u2032 Hydroxyflavanone activity in vitro and in vivo against wild-type and antimony-resistant Leishmania amazonensis. PLoS Neglected Trop. Dis., 12.","DOI":"10.1371\/journal.pntd.0006930"},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Cherrak, S.A., Merzouk, H., and Mokhtari-Soulimane, N. (2020). Potential bioactive glycosylated flavonoids as SARS-CoV-2 main protease inhibitors: A molecular docking and simulation studies. PLoS ONE, 15.","DOI":"10.31219\/osf.io\/k4h5f"},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Sajid, M., Channakesavula, C.N., Stone, S.R., and Kaur, P. (2021). Synthetic biology towards improved flavonoid pharmacokinetics. Biomolecules, 11.","DOI":"10.3390\/biom11050754"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1016\/j.sajb.2016.10.021","article-title":"Antimicrobial, antioxidant and cytotoxicity of isolated compounds from leaves of Pappea capensis","volume":"108","author":"Pendota","year":"2017","journal-title":"S. Afr. J. Bot."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1016\/j.freeradbiomed.2019.08.001","article-title":"Redox properties of individual quercetin moieties","volume":"143","author":"Biler","year":"2019","journal-title":"Free Radic. Biol. Med."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1016\/j.toxrep.2022.03.011","article-title":"An ethnopharmacological review on the therapeutical properties of flavonoids and their mechanisms of actions: A comprehensive review based on up to date knowledge","volume":"9","year":"2022","journal-title":"Toxicol. Rep."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4150897","DOI":"10.1155\/2020\/4150897","article-title":"Identification of six flavonoids as novel cellular antioxidants and their structure-activity relationship","volume":"2020","author":"Zhang","year":"2020","journal-title":"Oxidative Med. Cell. Longev."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Lou, Y., Xu, T., Cao, H., Zhao, Q., Zhang, P., and Shu, P. (2022). Natural antioxidants, tyrosinase and acetylcholinesterase inhibitors from Cercis glabra leaves. Molecules, 27.","DOI":"10.3390\/molecules27248667"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"7432","DOI":"10.3390\/molecules27217432","article-title":"Anti-inflammatory, antioxidative, and nitric oxide-scavenging activities of a quercetin nanosuspension with polyethylene glycol in LPS-induced RAW 264.7 macrophages","volume":"27","author":"Kang","year":"2022","journal-title":"Molecules"},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Khan, H., Ullah, H., Aschner, M., Cheang, W.S., and Akkol, E.K. (2020). Neuroprotective effects of quercetin in Alzheimer\u2019s disease. Biomolecules, 10.","DOI":"10.3390\/biom10010059"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Carrillo-Martinez, E.J., Flores-Hern\u00e1ndez, F.Y., Salazar-Montes, A.M., Nario-Chaidez, H.F., and Hern\u00e1ndez-Ortega, L.D. (2024). Quercetin, a flavonoid with great pharmacological capacity. Molecules, 29.","DOI":"10.20944\/preprints202402.0029.v1"},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Smyrska-Wieleba, N., and Mroczek, T. (2023). Natural inhibitors of cholinesterases: Chemistry, structure\u2013activity and methods of their analysis. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24032722"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"3219","DOI":"10.1016\/0040-4020(80)80168-2","article-title":"Iterative partial equalization of orbital electronegativity a rapid access to atomic charges","volume":"36","author":"Gasteiger","year":"1980","journal-title":"Tetrahedron"},{"key":"ref_48","unstructured":"Jones, G., Willett, P., Glen, R.C., Leach, A.R., and Taylor, R. (Gold, 2008). Gold, version 4.0."},{"key":"ref_49","unstructured":"ChemAxon (Marvin Sketch, 2015). Marvin Sketch, version 15.4.20."},{"key":"ref_50","unstructured":"Tripos (Sybyl-X, 2010). Sybyl-X, version 2.0."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"982","DOI":"10.1002\/jcc.540100804","article-title":"Validation of the general purpose Tripos 5.2 force field","volume":"10","author":"Clark","year":"1989","journal-title":"J. Comput. Chem."},{"key":"ref_52","unstructured":"Schr\u00f6dinger, LLC (The PyMOL Molecular Graphics System, 2009). The PyMOL Molecular Graphics System, version 1.3."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1021\/ml100164p","article-title":"Drawing the PDB\u2014Protein-ligand complexes in two dimensions","volume":"1","author":"Stierand","year":"2010","journal-title":"ACS Med. Chem. Lett."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/10\/1669\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,5,17]],"date-time":"2026-05-17T04:11:47Z","timestamp":1778991107000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/10\/1669"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,5,15]]},"references-count":53,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2026,5]]}},"alternative-id":["molecules31101669"],"URL":"https:\/\/doi.org\/10.3390\/molecules31101669","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,5,15]]}}}