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A Reaction Library to Predict Direct Photochemical Transformation Products of Environmental Organic Contaminants in Sunlit Aquat

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A Reaction Library to Predict Direct Photochemical Transformation Products of Environmental Organic Contaminants in Sunlit Aquat 1 Supporting Information for 2 A reaction library to predict direct 3 photochemical transformation products of 4 environmental organic contaminants in sunlit 5 aquatic systems 6 Chenyi Yuana, Caroline Tebes-Stevensb*, Eric J. Weberb 7 aOak Ridge Institute for Science and Education (ORISE), hosted at United States Environmental 8 Protection Agency, Athens, Georgia 30605, United States 9 bCenter for Environmental Measurement and Modeling, United States Environmental Protection 10 Agency, Athens, Georgia 30605, United States 11 12 Number of Pages: 34 13 Number of Lists: 2 14 Number of Figures: 8 15 Number of Tables: 1 16 S1 17 Table of Content Figure S1 The trend in number of peer-reviewed journal publication S3 investigating direct phototransformation products of aquatic contaminants under environmentally relevant conditions from 1960 to 2019. Figure S2 Example transformation assignment and reaction scheme selection for S4 hydroxychlorothalonil. Figure S3 Composition diagram of NO, NP, NOP. S5 Figure S4 An example of calculating evaluation counts based on compound- S6 specific performance, reaction-scheme-specific performance, and major-product performance. Figure S5 Plots of recall and precision for DB-J-ENV compounds after 1- S7 generation (a), 2-generation (b), and 3-generation (c) prediction. Figure S6 Library prediction example for hexahydro-1,3,5-trinitro-1,3,5-triazine S8 (RDX). Figure S7 Plot of recall and precision for DB-EFSA-ENV compounds after 1- S9 generation (a), 2-generation (b), and 3-generation (c) prediction. Figure S8 Characterization for the 46 reaction schemes observed in the first S10 generation evaluated for DB-EFSA-ENV. Table S1 List of direct photolysis reaction schemes and its corresponding S11-17 counts of experimental observed parent compounds (NO_r), predicted parent compounds (NP_r), correct prediction hits (NOP_r), and the corresponding precision as a result of first-generation transformation for different compound lists. List S1 Complete list of compound names and standardized smiles in DB-J- S18-29 ENV List S2 Complete list of compound names and standardized smiles in DB- S30-33 EFSA-ENV. References S34 18 19 20 S2 21 22 Figure S1. The trend in number of peer-reviewed journal publications investigating direct 23 phototransformation products of aquatic contaminants under environmentally relevant conditions 24 from 1960 to 2019. Data are from DB-J-ENV. S3 25 26 27 Figure S2. Example transformation assignment and reaction scheme selection for 28 hydroxychlorothalonil. The experimentally observed products are from a 2001 publication by 29 Armbrust.1 30 S4 31 32 Figure S3. Composition diagram of NO, NP, NOP. 33 S5 34 35 Figure S4. An example of calculating evaluation counts based on compound-specific 36 performance, reaction-scheme-specific performance, and major-product performance. For 37 simplification, this example only has first-generation products. S6 38 39 Figure S5. Plots of recall and precision for DB-J-ENV compounds after 1-generation (a), 2- 40 generation (b), and 3-generation (c) prediction. The size (and color) of circles represents count of 41 compounds of the same recall and precision. Recall/precision based on summation of all product 42 counts were tabulated in Table 1 and shown as the solid (black) lines. Mean and median of 43 individual recall/precision after removing 37 uncountable ones (denominator of precision is zero) 44 were shown as the dash (blue) and dot (red) lines, respectively. 45 46 S7 47 48 Figure S6. Library prediction example for hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX). 49 Experimentally observed products were compiled from literature.2, 3 Products a and b were only 50 proposed but no efforts were taken to detect them by the referenced papers. Please note this 51 manually created diagram is different from the output format of CTS. S8 52 53 Figure S7. Plot of recall and precision for DB-EFSA-ENV compounds after 1-generation (a), 2- 54 generation (b), and 3-generation (c) prediction. The size (and color) of circles represents count of 55 compounds of the same recall and precision. Recall/precision based on summation of all product 56 counts were tabulated in Table 1 and shown as the solid (black) lines. Mean and median of 57 individual recall/precision after removing 14 uncountable ones (denominator of precision is zero) 58 were shown as the dash (blue) and dot (red) lines, respectively. 59 60 S9 61 62 Figure S8. Characterization for the 46 reaction schemes observed in the first generation 63 evaluated for DB-EFSA-ENV. The size (and color) of circles represent count of reaction 64 schemes with the same NOP_r (number of parent compounds correctly predicted to undergo a 65 certain reaction scheme) and precision (NOP_r/NP_r). 66 S10 67 Table S1. List of direct photolysis reaction schemes and its corresponding counts of experimental observed parent compounds (NO_r), 68 predicted parent compounds (NP_r), correct prediction hits (NOP_r), and the corresponding precision as a result of first-generation 69 transformation for different compound lists. Precision is only applicable for reaction schemes with non-zero NP_r. DB-J-ENV DB-EFSA-ENV CERAPP # Reaction Scheme Name NO_r NOP_r NP_r precision NO_r NOP_r NP_r precision NP_r Photorearrangement 1 1-Naphthoxy Photorearrangement (C2) 1 1 2 0.5 1 1 1 1.0 41 2 1-Naphthoxy Photorearrangement (C4) 1 1 2 0.5 1 1 1 1.0 28 3 2-Naphthoxy Photorearrangement (C1) 0 0 4 0.0 0 0 0 50 4 2-Nitrobenzaldehyde Photorearrangement 1 1 1 1.0 0 0 0 5 5 Benzyl Phenyl Ether Photorearrangement (o) 1 1 2 0.5 1 1 1 1.0 110 6 Benzyl Phenyl Ether Photorearrangement (p) 1 1 1 1.0 1 1 1 1.0 64 7 Enone Steroid Photorearrangement to Cyclopentenone 2 2 2 1.0 0 0 0 125 8 Enone Steroid Photorearrangement to Lumiketone 2 2 2 1.0 0 0 0 125 9 O-aryl Carbamate Photorearrangement (o) 1 1 4 0.3 0 0 3 0.0 90 10 O-aryl Carbamate Photorearrangement (p) 1 1 4 0.3 0 0 2 0.0 53 11 Organothiophosphorus Ester Photochemical Oxygen Transfer 1 1 1 1.0 0 0 0 2 12 Organothiophosphorus Ester Photorearrangement 1 1 9 0.1 1 1 2 0.5 66 13 Phenoxyphenol Dehalogenative Photorearrangement 1 1 13 0.1 0 0 0 1 Photodissociation 14 Aromatic Ketone Norrish II Photocleavage (C1_C4) 1 1 1 1.0 0 0 0 101 15 Aminobenzophenone Photochemical N-dealkylation 1 1 1 1.0 0 0 0 58 16 Benzyl Photodeamination to Alcohol 2 2 8 0.3 0 0 3 0.0 562 17 Benzyl Photodeamination to Carbonyl 4 4 8 0.5 0 0 3 0.0 513 18 Benzyl Thiocarbamate Photocleavage to Carbonyl 2 2 3 0.7 0 0 0 5 19 Cyclohexanedione Oxime N-O Photocleavage 2 2 2 1.0 1 1 1 1.0 10 20 Diazepam Ring Photocleavage 5 5 5 1.0 0 0 0 47 21 Dihydrophenanthrene Benzyl Photodealkylation 1 1 2 0.5 0 0 0 1 22 Dihydrophenanthrene Benzyl Oxidative Photodealkylation 2 2 2 1.0 0 0 0 0 S11 DB-J-ENV DB-EFSA-ENV CERAPP # Reaction Scheme Name NO_r NOP_r NP_r precision NO_r NOP_r NP_r precision NP_r 23 Dinitroaniline Photochemical N-dealkylation 5 5 5 1.0 2 2 6 0.3 21 24 Fluoroquinolone Ethylenediamine Photochemical N-dealkylation 0 0 1 0.0 0 0 0 9 25 Fluoroquinolone Photochemical N-dealkylation 4 4 5 0.8 0 0 0 15 26 Fluoroquinolone Piperazine Photochemical Bis N-dealkylation 3 3 10 0.3 0 0 0 26 27 Imidazolinone Ring Photocleavage to Aldehyde 3 3 6 0.5 0 0 1 0.0 10 28 Imidazolinone Ring Photocleavage to Amide 3 3 6 0.5 1 1 1 1.0 10 29 Imidazolinone Ring Photocleavage to Amidine 3 3 6 0.5 0 0 1 0.0 10 30 Imidazolinone Ring Photocleavage to Carboxylic Acid 3 3 6 0.5 1 1 1 1.0 10 31 Nitroenamine Photocleavage 1 1 2 0.5 0 0 0 8 32 Nitroenamine Photocleavage to Carbonyl 2 2 2 1.0 0 0 0 8 33 Nitrosamine N-C Photocleavage 1 1 1 1.0 0 0 0 153 34 p-Aminobenzoic Acid Photochemical N-dealkylation 2 2 2 1.0 0 0 0 18 35 Phenoxyphenol Ether Photocleavage 7 7 13 0.5 0 0 0 2 36 Phenylurea Photochemical N-dealkylation 2 2 8 0.3 1 1 3 0.3 78 37 Phenylurea Photochemical N-demethoxylation 2 2 3 0.7 1 1 1 1.0 7 38 Phenylurea N-formyl Photocleavage 0 0 0 0 0 0 0 39 Pyridinium Photochemical N-dealkylation 3 3 3 1.0 0 0 0 201 40 s-Triazine Side Chain Photochemical N-dealkylation 8 8 13 0.6 4 4 7 0.6 138 41 Sulfonamide N-C Photocleavage (6-5) 5 5 7 0.7 0 0 0 26 42 Tetracycline Photochemical N-dealkylation 0 0 2 0.0 0 0 0 22 Photoelimination 43 1_2_4-Triazine-5-one Photochemical N-deamination 1 1 1 1.0 2 2 2 1.0 5 44 Aromatic Acetic Acid Photodecarboxylation 6 6 11 0.5 1 1 1 1.0 241 45 Aromatic Acetic Acid Photodecarboxylation to Alcohol 6 6 11 0.5 1 1 1 1.0 241 46 Aromatic Acetic Acid Photodecarboxylation to Carbonyl 8 8 10 0.8 1 1 1 1.0 204 47 Aromatic Carboxylic Acid Photodecarboxylation 7 7 28 0.3 0 0 5 0.0 881 48 Aromatic Carboxylic Acid Photodecarboxylation to Alcohol 2 2 28 0.1 0 0 5 0.0 881 49 Benzotriazole Photodenitrogenation 5 5 5 1.0 0 0 0 90 S12 DB-J-ENV DB-EFSA-ENV CERAPP # Reaction Scheme Name NO_r NOP_r NP_r precision NO_r NOP_r NP_r precision NP_r 50 Benzotriazole Photodenitrogenation to Phenol (o) 4 4 5 0.8 0 0 0 90 51 Cephem Photodecarboxylation 3 3 4 0.8 0 0 0 82 52 Cyanohydrin Cyano Photoelimination to Aldehyde 0 0 0 0 0 0 0 53 Fipronil Sulfoxide Photoextrusion 1 1 1 1.0 1 1 1 1.0 1 54 Imidazolinone Amide Photoelimination 2 2 6 0.3 0 0 1 0.0 10 55 Imidazolinone Photodecarbonylation 3 3 6 0.5 0 0 1 0.0 10 56 Nitroguanidine Photochemical N-denitration 2 2 4 0.5 1 1 1 1.0 15 57 Nitrosamine N-N Photocleavage 1 1 1 1.0 0 0 0 157 58 Phenoxyacetic Acid Photodecarboxylation 2 2 11 0.2 0 0 5 0.0 93 59 Phenoxyacetic Acid Photodecarboxylation to Carbonyl 2 2 11 0.2 1 1 5 0.2 93 60 Pyrrolinone Photodecarbonylation 0 0 0 0 0 0 1 61 RDX Photochemical N-denitration to Imine 1 1
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