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Mining Electronic Laboratory Notebooks: Analysis, Retrosynthesis, and Reaction Based Enumeration

An approach to automatically analyze and use the knowledge contained in electronic laboratory notebooks (ELNs) has been developed. Reactions were reduced to their reactive center and converted to a string representation (SMIRKS) which formed the basis for reaction classification and in silico (retro-)synthesis. Of the SMIRKS that occurred at least five times, 98% successfully regenerated the original product. The extracted reaction rules (SMIRKS) and corresponding reactants span a virtual chemical space which showed a strong dependence on the size of the reactive center. Whereas relatively few robust reaction types were sufficient to describe a large part of all reactions, considerably more reaction rules were necessary to cover all reactions in the ELN. Furthermore, reaction sequences were extracted to identify frequent combinations and diversifying reaction steps. Based on the extracted knowledge a (retro-)synthesis tool was built allowing for de novo design of compounds which have a high chance of bein...

Authors:   Clara D. Christ; Matthias Zentgraf; Jan M. Kriegl
Journal:   Journal of Chemical Information and Modeling
Year:   2012
DOI:   10.1021/ci300116p
Publication date:   15-Jun-2012
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