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In this study, we develop a system that generates virtual compound libraries from input compounds. When a user inputs a compound, the system recursively applies virtual synthetic reaction rules to the compound to improve its properties. The synthetic pathway can also be traced by the user because the reaction rules in this system are based on real organic synthesis reactions. This system has useful functions for effective drug design, such as structural preservation, allowing the substructures necessary for potency to be maintained. In this paper, to confirm the effect of directional reaction sets, we applied the reaction sets to 100 compounds. Moreover, to confirm that the system can reproduce real synthetic pathways, the synthetic pathways of Ibuprofen and Ofloxacin were explored by inputting isobutyl benzene and 7,8-difluoro-2,3-dihydro-3-methyl-4H-benzoxazine. This application is available at the following URL: http:\/\/enh.sekijima-lab.org . <\/jats:p>","DOI":"10.1142\/s0219720018400164","type":"journal-article","created":{"date-parts":[[2018,5,3]],"date-time":"2018-05-03T06:12:46Z","timestamp":1525327966000},"page":"1840016","source":"Crossref","is-referenced-by-count":5,"title":["Compound property enhancement by virtual compound synthesis"],"prefix":"10.1142","volume":"16","author":[{"given":"Naoki","family":"Arai","sequence":"first","affiliation":[{"name":"Department of Computer Science, Tokyo Institute of Technology, 4259-J3-23, Nagatsuta-cho, Midori-ku, 226-8502, Yokohama, Japan"}]},{"given":"Shunsuke","family":"Yoshikawa","sequence":"additional","affiliation":[{"name":"Department of Computer Science, Tokyo Institute of Technology, 4259-J3-23, Nagatsuta-cho, Midori-ku, 226-8502, Yokohama, Japan"}]},{"given":"Nobuaki","family":"Yasuo","sequence":"additional","affiliation":[{"name":"Department of Computer Science, Tokyo Institute of 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