{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T10:04:47Z","timestamp":1792663487362,"version":"4.5.0"},"reference-count":19,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2021,7,3]],"date-time":"2021-07-03T00:00:00Z","timestamp":1625270400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2021,7,3]],"date-time":"2021-07-03T00:00:00Z","timestamp":1625270400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/100007569","name":"Carl-Zeiss-Stiftung","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007569","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"crossref","award":["239748522"],"award-info":[{"award-number":["239748522"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/100012957","name":"Friedrich-Schiller-Universit\u00e4t Jena","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100012957","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["J Cheminform"],"published-print":{"date-parts":[[2021,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The generation of constitutional isomer chemical spaces has been a subject of cheminformatics since the early 1960s, with applications in structure elucidation and elsewhere. In order to perform such a generation efficiently, exhaustively and isomorphism-free, the structure generator needs to ensure the building of canonical graphs already during the generation step and not by subsequent filtering. Here we present MAYGEN, an open-source, pure-Java development of a constitutional isomer molecular generator. The principles of MAYGEN\u2019s architecture and algorithm are outlined and the software is benchmarked in single-threaded mode against the state-of-the-art, but closed-source solution MOLGEN, as well as against the best open-source solution PMG. Based on the benchmarking, MAYGEN is on average 47 times faster than PMG and on average three times slower than MOLGEN in performance.<\/jats:p>","DOI":"10.1186\/s13321-021-00529-9","type":"journal-article","created":{"date-parts":[[2021,7,3]],"date-time":"2021-07-03T05:02:49Z","timestamp":1625288569000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["MAYGEN: an open-source chemical structure generator for constitutional isomers based on the orderly generation principle"],"prefix":"10.1186","volume":"13","author":[{"given":"Mehmet Aziz","family":"Yirik","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria","family":"Sorokina","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6966-0814","authenticated-orcid":false,"given":"Christoph","family":"Steinbeck","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2021,7,3]]},"reference":[{"issue":"2","key":"529_CR1","doi-asserted-by":"publisher","first-page":"342","DOI":"10.1021\/ci600423u","volume":"47","author":"T Fink","year":"2007","unstructured":"Fink T, Reymond J-L (2007) Virtual exploration of the chemical universe up to 11 atoms of c, n, o, f: assembly of 26.4 million structures (110.9 million stereoisomers) and analysis for new ring systems, stereochemistry, physicochemical properties, compound classes, and drug discovery. J Chem Inf Model 47(2):342\u2013353","journal-title":"J Chem Inf Model"},{"issue":"25","key":"529_CR2","doi-asserted-by":"publisher","first-page":"8732","DOI":"10.1021\/ja902302h","volume":"131","author":"LC Blum","year":"2009","unstructured":"Blum LC, Reymond J-L (2009) 970 million druglike small molecules for virtual screening in the chemical universe database GSB-13. J Am Chem Soc 131(25):8732\u20138733","journal-title":"J Am Chem Soc"},{"issue":"11","key":"529_CR3","doi-asserted-by":"publisher","first-page":"2864","DOI":"10.1021\/ci300415d","volume":"52","author":"L Ruddigkeit","year":"2012","unstructured":"Ruddigkeit L, Van Deursen R, Blum LC, Reymond J-L (2012) Enumeration of 166 billion organic small molecules in the chemical universe database GDB-17. J Chem Inf Model 52(11):2864\u20132875","journal-title":"J Chem Inf Model"},{"key":"529_CR4","unstructured":"Sutherland G (1967) Dendral\u2014a computer program for generating and filtering chemical structures. 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