Reaction Library to Predict Direct Photochemical Transformation Products of Environmental Organic Contaminants in Sunlit Aquatic Systems

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Abstract
Cheminformatics-based applications to predict transformation pathways of environmental contaminants are useful to quickly prioritize contaminants with potentially toxic/persistent products. Direct photolysis can be an important degradation pathway for sunlight-absorbing compounds in the aquatic systems. In this study, we developed the first freely available direct phototransformation pathway predictive tool, which uses a rule-based reaction library. Journal publications studying diverse contaminants (such as pesticides, pharmaceuticals, and energetic compounds) were systematically compiled to encode 155 reaction schemes into the reaction library. The execution result of this predictive tool was internally evaluated against 390 compounds from the compiled journal publications and externally evaluated against 138 compounds from regulatory reports. The recall (sensitivity) and precision (selectivity) were 0.62 and 0.35, respectively, for internal evaluation, and 0.56 and 0.20, for external evaluation, when only products formed from the first reaction step were counted. This predictive tool could help to narrow the data gaps in chemical registration/evaluation and inform future experimental studies.
Funding Information
  • Oak Ridge Institute for Science and Education (DW-922983301-01)
  • U.S. Environmental Protection Agency (DW-922983301-01)

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