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

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20

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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.

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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

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31

32 Figure S3. Composition diagram of NO, NP, NOP.

33

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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.

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46

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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.

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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.

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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

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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 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

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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

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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 1 1.0 0 0 0 2 62 Sulfonamide SO2 Extrusion Photorearrangement (6-6) 5 5 7 0.7 0 0 0 26 Photocyclization 63 Acetanilide Dehalogenative Photocyclization to Pyrrolinone 1 1 1 1.0 0 0 0 1 64 Acetanilide O-dealkyl Dehalogenative Photocyclization to 2 2 2 1.0 1 1 1 1.0 12 Morpholinone 65 Photocycloaddition 1 1 1 1.0 0 0 0 1 66 Aminobenzophenone Photocyclization to Acridinone 2 2 2 1.0 0 0 0 15 67 Anthranilic Diamide Dehalogenative Photocyclization to Oxazine 2 2 2 1.0 2 2 2 1.0 7 68 Aromatic Ketone Norrish II Photocyclization (C1_C4) 1 1 1 1.0 0 0 0 107 69 beta-Triketone Dehalogenative Photocyclization to Pyran 2 2 2 1.0 0 0 2 0.0 2 70 Diarylethene Photocyclization to Phenanthrene 1 1 1 1.0 0 0 0 35 71 Diarylethene Photocyclization to Phenanthrene (E isomer) 2 2 5 0.4 0 0 0 152 72 Dinitroaniline Photocyclization to Benzimidazole (NOHOH) 1 1 3 0.3 0 0 5 0.0 16 73 Dinitroaniline Photocyclization to Benzimidazole (NOHOH to 0 0 1 0.0 0 0 0 0 NO) 74 Dinitroaniline Photocyclization to Benzimidazole (NO to N) 1 1 1 1.0 0 0 0 0

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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 75 Diphenylamine Photocyclization to Carbazole 1 1 2 0.5 1 1 1 1.0 317 76 Diphenylamine Dehalogenative Photocyclization to Carbazole 1 1 1 1.0 0 0 0 13 77 Fluoroquinolone Defluorinative Photocyclization 1 1 1 1.0 0 0 0 3 78 Lamotrigine Photocyclization to Carbazole 1 1 1 1.0 0 0 0 5 79 Lamotrigine Dehalogenative Photocyclization to Carbazole 1 1 1 1.0 0 0 0 3 80 o-Vinylbiphenyl Photocyclization to Dihydrophenanthrene 2 2 2 1.0 0 0 0 14 81 Phenoxyphenol Dehalogenative Photocyclization to Dioxin 13 13 13 1.0 0 0 0 1 Photochemical Ring Contraction 82 Zepine Photochemical Ring Contraction to Acridine 1 1 1 1.0 0 0 0 7 Photohydrolysis 83 Aromatic Amine Photohydrolysis 1 1 19 0.1 0 0 1 0.0 1253 84 Aromatic Carbamate Photohydrolysis 3 3 7 0.4 3 3 5 0.6 201 85 Aromatic Ether Photohydrolysis 21 21 51 0.4 22 22 50 0.4 3232 86 Aromatic Halide Photohydrolysis 55 55 160 0.3 11 11 64 0.2 4560 87 Aromatic Nitro Photohydrolysis 13 13 48 0.3 1 1 11 0.1 1313 88 Aromatic Sulfonate Photohydrolysis 10 10 10 1.0 1 1 1 1.0 51 89 Benzoylphenylurea Amide Photohydrolysis 2 2 2 1.0 0 0 5 0.0 14 90 Benzoylphenylurea Photohydrolysis 1 1 2 0.5 4 4 5 0.8 14 91 beta-Triketone alpha Photocleavage to Carboxylic Acid 3 3 3 1.0 1 1 2 0.5 4 92 Diphenyl Ether Photohydrolysis 10 9 19 0.5 11 11 24 0.5 328 93 Fluoroquinolone Fluoride Photohydrolysis 5 5 8 0.6 0 0 0 31 94 N-aryl Amide Photohydrolysis 6 6 23 0.3 4 4 9 0.4 1119 95 Nitrofuran Imine Photohydrolysis 3 3 3 1.0 0 0 0 22 96 Nitroguanidine Imine Photohydrolysis 3 3 3 1.0 1 1 1 1.0 15 97 Nitroguanidine Nitro Photohydrolysis 1 1 1 1.0 0 0 0 1 98 Organophosphorus Ester Photohydrolysis 8 8 10 0.8 1 1 3 0.3 138 99 Pyrethroid Carboxylic Acid Ester Photohydrolysis 3 3 4 0.8 4 4 5 0.8 160 100 Pyrrolinone Halide Photohydrolysis 0 0 0 0 0 0 0

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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 101 Sulfonamide Photohydrolysis 9 9 18 0.5 4 4 5 0.8 219 102 Sulfonamide S-C Photohydrolysis 7 7 27 0.3 1 1 4 0.3 314 103 Sulfonylurea Photohydrolysis 7 7 7 1.0 2 2 4 0.5 45 104 Sulfonylurea S-C Photohydrolysis 3 3 7 0.4 2 2 4 0.5 45 105 Sulfonylurea S-N Photohydrolysis 5 5 7 0.7 3 3 4 0.8 45 106 Trifluoromethyl Photohydrolysis 6 6 23 0.3 0 0 23 0.0 347 Photohydration 107 Diarylethene Photohydration 4 4 6 0.7 0 0 0 205 108 Dienone Steroid Photohydration (C5) 2 2 4 0.5 0 0 0 22 109 Dienone Steroid Photohydration (C9) 1 1 1 1.0 0 0 0 15 110 Enone Steroid Photohydration and Photorearrangement to Spiro 2 2 2 1.0 0 0 0 125 111 Trienone Steroid Photohydration (C10) 1 1 3 0.3 0 0 0 7 112 Trienone Steroid Photohydration (C12) 2 2 3 0.7 0 0 0 7 Photooxidation 113 1_2-Naphthoquinone Photohydroxylation (C4) 0 0 0 0 0 0 1 114 1_4-Naphthoquinone Photohydroxylation (C5) 1 1 1 1.0 0 0 1 0.0 22 115 1_4-Naphthoquinone Photohydroxylation (C6) 1 1 1 1.0 0 0 1 0.0 25 116 1-Hydroxypyrene Photooxidation to Quinone (C1_C6) 1 1 1 1.0 0 0 0 1 117 1-Hydroxypyrene Photooxidation to Quinone (C1_C8) 1 1 1 1.0 0 0 0 1 118 1-Naphthol Photooxidation to 1_2-Benzoquinone 1 1 2 0.5 0 0 0 76 119 1-Naphthol Photooxidation to 1_4-Benzoquinone 2 2 2 1.0 0 0 0 271 120 1-Naphthoxy Oxidative Photocleavage to 1_4-Benzoquinone 2 2 3 0.7 0 0 1 0.0 29 121 Anthracene Photooxidation to Endoperoxide 2 2 2 1.0 0 0 0 56 122 Aromatic Methyl Photooxidation to Carboxylic Acid 2 2 2 1.0 1 1 1 1.0 2 123 Aromatic Nitroso Photooxidation 2 2 2 1.0 0 0 0 17 124 Aromatic Sulfoxide Photooxidation 1 1 2 0.5 0 0 1 0.0 49 125 Aromatic Thioether Photooxidation 4 4 8 0.5 3 3 5 0.6 522 126 Benzaldehyde Photooxidation to Carboxylic Acid 3 3 5 0.6 0 0 0 179

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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 127 Benzyl Thio Photooxidation to Sulfoxide 2 2 3 0.7 0 0 1 0.0 99 128 beta-Triketone alpha Photohydroxylation (Dienol) 1 1 1 1.0 0 0 0 0 129 beta-Triketone alpha Photohydroxylation (Keto) 2 2 5 0.4 0 0 1 0.0 9 130 beta-Triketone Photohydroxylation (Enol) 1 1 1 1.0 0 0 0 2 131 beta-Triketone Photohydroxylation (Keto) 4 4 4 1.0 0 0 1 0.0 6 132 Carbamazepine Photoepoxidation 1 1 1 1.0 0 0 0 7 133 Diarylethene Photooxidation 4 4 6 0.7 0 0 0 205 134 Dihydrooxathiine Anilide Photooxidation to Sulfoxide 1 1 1 1.0 1 1 1 1.0 1 135 Dihydropyridine Photooxidation to 1 1 1 1.0 0 0 0 0 136 Octahydrophenanthrene Benzyl Photohydroxylation 3 3 4 0.8 0 0 0 111 137 Octahydrophenanthrene Benzyl Photooxidation to Ketone 3 3 4 0.8 0 0 0 109 138 Organothiophosphorus Ester Photooxidation to Oxon 6 6 9 0.7 1 1 2 0.5 66 139 Phenylurea N-methyl Photooxidation to N-formyl 2 2 8 0.3 0 0 2 0.0 83 140 Pyrene Aromatic Photohydroxylation 0 0 1 0.0 0 0 0 10 141 s-Triazine Side Chain N-alkyl Photooxidation to Carbonyl 4 4 9 0.4 1 1 6 0.2 152 142 s-Triazine Side Chain N-isopropyl Photooxidation to Ketone 2 2 4 0.5 0 0 0 23 143 Trienone Steroid Photooxidation to Dialdehyde 1 1 3 0.3 0 0 0 7 144 Trifluoroacetic Acid Photoformation 0 0 0 0 0 0 0 Photoreduction 145 Aromatic Photohydrodehalogenation 41 41 160 0.3 6 6 64 0.1 4560 146 Dinitroaniline Nitro Photoreduction 1 1 5 0.2 2 2 7 0.3 34 147 Fluoroquinolone Photohydrodefluorination 1 1 11 0.1 0 0 0 43 Secondary Dark Reaction 148 12-OH Steroid Dehydration to Trienone 0 0 0 0 0 0 0 149 5-OH Steroid Dehydration to Dienone 0 0 0 0 0 0 0 150 Aldehyde Oxidation to Carboxylic Acid 0 0 0 0 0 0 477 151 C-NCO Hydrolysis 0 0 0 0 0 0 30 152 C-NNO2 Hydrolysis 0 0 0 0 0 0 17

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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 153 Dehydration of Geminal Diols 0 0 0 0 0 0 26 154 Hydroxy Enal Tautomerization 0 0 0 0 0 0 0 155 Nitro Amidine Hydrolysis 0 0 0 0 0 0 0 70 71 Note: DB-J-ENV stands for the database of 390 compounds compiled from peer-reviewed journal publications on environmentally relevant 72 studies. DB-EFSA-ENV stands for the database of 138 compounds compiled from European Food Safety Authority reports on environmentally 73 relevant studies. CERAPP stands for the prediction list of 32,464 compounds from Collaborative Estrogen Receptor Activity Prediction Project 74 (CERAPP) to include a large portion of manufactured organic chemicals with environmental exposure potential. See the main article for more 75 details.

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76 List S1. Complete list of compound names and standardized smiles in DB-J-ENV. Name Standardized Smiles 1,2,7,8-tetrachlorodibenzo- Clc1ccc2Oc3cc(Cl)c(Cl)cc3Oc2c1Cl p-dioxin 1,2,7,8- Clc1ccc2oc3cc(Cl)c(Cl)cc3c2c1Cl tetrachlorodibenzofuran 1,4-naphthoquinone O=C1C=CC(=O)c2ccccc12 1-(2-chlorobenzoyl)-3-(4- Clc1ccc(NC(=O)NC(=O)c2ccccc2Cl)cc1 chlorophenyl) urea 1-(3- N#CCCC[n+]1ccccc1 cyanopropyl)pyridinium 1-butyl-4- CCCC[n+]1ccc(C)cc1 methylpyridinium 1-ethylpyridinium CC[n+]1ccccc1 1-hydroxypyrene Oc1ccc2ccc3cccc4ccc1c2c34 1-methyl-5-carboxylic Cn1nnc2cc(ccc12)C(O)=O acid-benzotriazole 1-methylnaphthalene Cc1cccc2ccccc12 1-naphthaldehyde O=Cc1cccc2ccccc12 1-naphthaleneacetic acid OC(=O)Cc1cccc2ccccc12 1-naphthalenemethanol OCc1cccc2ccccc12 1-naphthol Oc1cccc2ccccc12 17α-ethinylestradiol CC12CCC3C(CCc4cc(O)ccc34)C1CCC2(O)C#C 17β- CC12CCC3C(CCc4cc(O)ccc34)C1CCC2O 1H-benzotriazole c1ccc2[nH]nnc2c1 2'-HO BDE 68 Oc1c(Br)cc(Br)cc1Oc1ccc(Br)cc1Br 2'-HO PBDE 28 Oc1cc(Br)ccc1Oc1ccc(Br)cc1Br 2,2',3,3'- Clc1cccc(c1Cl)-c1cccc(Cl)c1Cl tetrachlorobiphenyl 2,2',5,5'- Clc1ccc(Cl)c(c1)-c1cc(Cl)ccc1Cl tetrachlorobiphenyl 2,2'-bis(4- OC(=O)C(c1ccc(Cl)cc1)c1ccc(Cl)cc1 chlorophenyl)acetic acid 2,3,7,8- Clc1cc2oc3cc(Cl)c(Cl)cc3c2cc1Cl tetrachlorodibenzofuran 2,4,5- OC(=O)COc1cc(Cl)c(Cl)cc1Cl trichlorophenoxyacetic acid 2,4,6-trinitrotoluene Cc1c(cc(cc1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 2,4,7- CN(C)S(=O)(=O)c1ccc2c(cc(c(OS(=O)(=O)c3ccccc3)c2c1)S(= tris(dimethylsulfamoyl)nap O)(=O)N(C)C)S(=O)(=O)N(C)C hthalen-1-yl benzenesulfonate 2,4-dichlorobiphenyl Clc1ccc(c(Cl)c1)-c1ccccc1

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Name Standardized Smiles 2,4-dichlorophenol Oc1ccc(Cl)cc1Cl 2,4-dichlorophenoxyacetic OC(=O)COc1ccc(Cl)cc1Cl acid 2,4-dichlorophenoxyacetic CCCCOCCOC(=O)COc1ccc(Cl)cc1Cl butoxyethyl ester 2,4-dinitroanisole COc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O 2,4-dinitrophenol Oc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O 2,5-dichlorobiphenyl Clc1ccc(Cl)c(c1)-c1ccccc1 2,6-dimethylbenzoquinone CC1=CC(=O)C=C(C)C1=O 2,6-dinitro-N-propyl-4- CCCNc1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O (trifluoromethyl) 2,7-dichlorodibenzofuran Clc1ccc2c(c1)oc1ccc(Cl)cc21 2-(2-naphthoxy)propionic CC(Oc1ccc2ccccc2c1)C(O)=O acid 2-amino-5- Nc1ccc(Cl)cc1C(=O)c1ccccc1 chlorobenzophenone 2-chloro-4-nitroaniline Nc1ccc(cc1Cl)[N+]([O-])=O 2-chloro-4- Oc1ccc(cc1Cl)[N+]([O-])=O 2-chloro-5- Oc1cc(ccc1Cl)C(F)(F)F trifluoromethylphenol 2-chlorophenol Oc1ccccc1Cl 2-ethyl-4-nitro-3-propyl-6- CCCN1c2c(cc(cc2[N+]([O-])=O)C(F)(F)F)N(O)C1(O)CC (trifluoromethyl)-1,3- benzodiazole-1,2-diol 2-ethyl-4-nitro-6- CCc1[nH]c2c(cc(cc2[n+]1[O-])C(F)(F)F)[N+]([O-])=O (trifluoromethyl)-3H-1,3- benzodiazol-1-ium-1-olate 2-mercaptobenzothiazole Sc1nc2ccccc2s1 2-methyl-1,4- CC1=CC(=O)C=CC1=O benzoquinone 2-methylquinolin-8-yl Cc1ccc2cccc(OS(=O)(=O)c3ccccc3)c2n1 benzenesulfonate 2-naphthoxyacetic acid OC(=O)COc1ccc2ccccc2c1 2-nitrobenzaldehyde [O-][N+](=O)c1ccccc1C=O 2-nitrophenol Oc1ccccc1[N+]([O-])=O 2-phenylbenzimidazole-5- OS(=O)(=O)c1ccc2[nH]c(nc2c1)-c1ccccc1 sulfonic acid 3,4-dichloroaniline Nc1ccc(Cl)c(Cl)c1 3,5-Cl-6-OH PBDE 47 Oc1c(Cl)c(Br)c(Cl)c(Br)c1Oc1ccc(Br)cc1Br 3,5-diamino- Nc1cc(N)cc(c1)C(F)(F)F trifluoromethyl-benzene 3,5-dibromomethylparaben COC(=O)c1cc(Br)c(O)c(Br)c1 3,5-dichloromethylparaben COC(=O)c1cc(Cl)c(O)c(Cl)c1

S19

Name Standardized Smiles 3-Cl-6-OH PBDE 47 Oc1cc(Br)c(Cl)c(Br)c1Oc1ccc(Br)cc1Br 3-bromomethylparaben COC(=O)c1ccc(O)c(Br)c1 3-chloromethylparaben COC(=O)c1ccc(O)c(Cl)c1 3-chlorophenol Oc1cccc(Cl)c1 3-chlorophenylacetic acid OC(=O)Cc1cccc(Cl)c1 3-hydroxybenzonitrile Oc1cccc(c1)C#N 3-methyl-4- CSc1ccc(O)cc1C (methylsulfanyl)phenol 3-nitro-4,5-dihydro-1H- [O-][N+](=O)c1n[nH]c(=O)[nH]1 1,2,4-triazol-5-one 3-nitrophenyl phosphate OP(O)(=O)Oc1cccc(c1)[N+]([O-])=O 3-nitrophenyl sulfate OS(=O)(=O)Oc1cccc(c1)[N+]([O-])=O 3-phenoxybenzoic acid OC(=O)c1cccc(Oc2ccccc2)c1 3-trifluoromethyl-4- Oc1ccc(c(c1)C(F)(F)F)[N+]([O-])=O nitrophenol 3-trifluoromethylphenol Oc1cccc(c1)C(F)(F)F 4,4'-dichlorobenzhydrol OC(c1ccc(Cl)cc1)c1ccc(Cl)cc1 4,4'-dichlorobenzilic acid OC(=O)C(O)(c1ccc(Cl)cc1)c1ccc(Cl)cc1 4,4'-dichlorobiphenyl Clc1ccc(cc1)-c1ccc(Cl)cc1 4,6-Cl- Oc1c(Oc2ccc(Cl)cc2Cl)cc(Cl)c(Cl)c1Cl 4-Cl-triclosan Oc1cc(Cl)c(Cl)cc1Oc1ccc(Cl)cc1Cl 4-OH-benzotriazole Oc1cccc2[nH]nnc12 4-amino-3- Nc1ccc(O)cc1C(F)(F)F trifluoromethylphenol 4-aminobenzoic acid Nc1ccc(cc1)C(O)=O 4-chloro-2-methylphenol Cc1cc(Cl)ccc1O 4-chloroaniline Nc1ccc(Cl)cc1 4-chlorobenzaldehyde Clc1ccc(C=O)cc1 4-chlorobenzoic acid OC(=O)c1ccc(Cl)cc1 4-chloronitrosobenzene Clc1ccc(cc1)N=O 4-chlorophenol Oc1ccc(Cl)cc1 4-chlorophenoxyacetic acid OC(=O)COc1ccc(Cl)cc1 4-hydroxycatechol Oc1ccc(O)c(O)c1 4-methyl-1H-benzotriazole Cc1cccc2[nH]nnc12 4-nitro butamifos CCOP(=S)(NC(C)CC)Oc1ccc(c(C)c1)[N+]([O-])=O 4-nitrobenzaldehyde [O-][N+](=O)c1ccc(C=O)cc1 4-nitrocatechol Oc1ccc(cc1O)[N+]([O-])=O 4-nitrophenol Oc1ccc(cc1)[N+]([O-])=O 4-nitroso sulfamethoxazole Cc1cc(NS(=O)(=O)c2ccc(cc2)N=O)no1 4-pentafluorothio-phenol Oc1ccc(cc1)S(F)(F)(F)(F)F 5,6,7,8-tetrahydro-2- Oc1ccc2CCCCc2c1 naphthol

S20

Name Standardized Smiles 5,6-dimethyl-2- CNc1nc(C)c(C)c(OC(=O)N(C)C)n1 (methylamino)pyrimidin-4- yl N,N-dimethylcarbamate 5,7- CN(C)S(=O)(=O)c1cc(c2ccc(C)nc2c1OS(=O)(=O)c1ccccc1)S(= bis(dimethylsulfamoyl)-2- O)(=O)N(C)C methylquinolin-8-yl benzenesulfonate 5-(dimethylsulfamoyl)-2- CN(C)S(=O)(=O)c1ccc(OS(=O)(=O)c2c(F)c(F)c(F)c(F)c2F)c2n methylquinolin-8-yl c(C)ccc12 2,3,4,5,6- pentafluorobenzenesulfona te 5-(dimethylsulfamoyl)-2- CN(C)S(=O)(=O)c1ccc(OS(=O)(=O)c2ccc(Br)cc2)c2nc(C)ccc1 methylquinolin-8-yl 4- 2 bromobenzenesulfonate 5-(dimethylsulfamoyl)-2- COc1ccc(cc1)S(=O)(=O)Oc1ccc(c2ccc(C)nc12)S(=O)(=O)N(C) methylquinolin-8-yl 4- C methoxybenzenesulfonate 5-(dimethylsulfamoyl)-2- CN(C)S(=O)(=O)c1ccc(OS(=O)(=O)c2ccccc2)c2nc(C)ccc12 methylquinolin-8-yl benzenesulfonate 5-(dimethylsulfamoyl)-2- CN(C)S(=O)(=O)c1ccc(OS(C)(=O)=O)c2nc(C)ccc12 methylquinolin-8-yl methanesulfonate 5-Cl-6-OH PBDE 47 Oc1c(Cl)c(Br)cc(Br)c1Oc1ccc(Br)cc1Br 5-[8-fluoro-4-isopropyl-2- CC(C)c1nc(nc-2c1CC(C(O)CC(O)CC(O)=O)c1cc(F)ccc- (N- 21)N(C)S(C)(=O)=O methylmethanesulfonamid o)-5H,6H- benzo[h]quinazolin-6-yl]- 3,5-dihydroxypentanoic acid 5-bromo-6-methyl-1,3- Cc1[nH]c(=O)[nH]c(=O)c1Br dihydropyrimidine-2,4- dione 5-carboxylic acid- OC(=O)c1ccc2[nH]nnc2c1 benzotriazole 5-chloro-2- CCC(=O)Nc1cccc(Cl)c1 methylacetanilide 5-chloro-2- CNc1ccc(Cl)cc1C(=O)c1ccccc1 methylaminobenzophenone 5-chlorosalicylic acid OC(=O)c1cc(Cl)ccc1O 5-fluorouracil Fc1c[nH]c(=O)[nH]c1=O 5-hydroxyl-1-naphthol Oc1cccc2c(O)cccc12

S21

Name Standardized Smiles 5-methyl-1H-benzotriazole Cc1ccc2[nH]nnc2c1 5-{3-fluoro-7-isopropyl- CC(C)n1c2CC(C(O)CC(O)CC(O)=O)c3cc(F)ccc3-c2c2ccccc12 5H,6H-benzo[c]carbazol-5- yl}-3,5- dihydroxypentanoic acid 6'-OH PBDE 100 Oc1cc(Br)cc(Br)c1Oc1c(Br)cc(Br)cc1Br 6'-OH PBDE 188 Oc1cc(Br)c(Br)cc1Oc1cc(Br)c(Br)cc1Br 6-Cl-triclosan Oc1c(Oc2ccc(Cl)cc2Cl)ccc(Cl)c1Cl 6-OH PBDE 47 Oc1cc(Br)cc(Br)c1Oc1ccc(Br)cc1Br 6-OH PBDE 99 Oc1c(Br)c(Br)cc(Br)c1Oc1ccc(Br)cc1Br 6- CNC(=O)N(C)c1nc2ccc(O)cc2s1 hydroxymethabenzthiazuro n 6-mercaptopurine S=c1nc[nH]c2nc[nH]c12 7,12- Cc1c2ccccc2c(C)c2c1ccc1ccccc21 dimethylbenz[a]anthracene 9,10-dioxoanthracen-2-yl O=C1c2ccccc2C(=O)c2cc(OS(=O)(=O)c3ccccc3)ccc12 benzenesulfonate 9-hydroxyfluorene OC1c2ccccc2-c2ccccc12 BDE 47 Brc1ccc(Oc2ccc(Br)cc2Br)c(Br)c1 N-(3-chloro-4- CCC(=O)Nc1ccc(O)c(Cl)c1 hydroxyphenyl)propanami de N-(4-chloro-3- CCC(=O)Nc1ccc(Cl)c(O)c1 hydroxyphenyl)propanami de N-(4-chlorophenyl)- Clc1ccc(NS(=O)(=O)c2ccccc2)cc1 benzenesulonamide N-(4- CCC(=O)Nc1ccc(Cl)cc1 chlorophenyl)propanamide N-(α-trichloromethyl-p- COc1ccc(NC(c2ccc(OC)cc2)C(Cl)(Cl)Cl)cc1 methoxybenzyl)-p- methoxyaniline N-acetyl sulfadiazine CC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1ncccn1 N-acetyl sulfamethazine CC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1nc(C)cc(C)n1 N-acetyl sulfamethoxazole CC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1cc(C)on1 N-methyl-4-aminobenzoic CNc1ccc(cc1)C(O)=O acid N-nitrosodimethylamine CN(C)N=O SYP-Z048 CN1OC(CC1(C)c1cccnc1)c1ccc(Cl)cc1 acebutolol CCCC(=O)Nc1ccc(OCC(O)CNC(C)C)c(c1)C(C)=O acesulfame CC1=CC(=O)NS(=O)(=O)O1 acetaminophen CC(=O)Nc1ccc(O)cc1

S22

Name Standardized Smiles OC(=O)c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1[N+]([O-])=O acifluorfen isomer OC(=O)c1cc(Oc2cc(ccc2Cl)C(F)(F)F)ccc1[N+]([O-])=O CCc1cccc(CC)c1N(COC)C(=O)CCl aldicarb CNC(=O)ON=CC(C)(C)SC alloxydim CCCC(=NOCC=C)C1=C(O)C(C(=O)OC)C(C)(C)CC1=O alprazolam Cc1nnc2CN=C(c3ccccc3)c3cc(Cl)ccc3-n12 altrenogest CC12C=CC3=C4CCC(=O)C=C4CCC3C1CCC2(O)CC=C amidosulfuron COc1cc(OC)nc(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)n1 amisulpride CCN1CCCC1CNC(=O)c1cc(c(N)cc1OC)S(=O)(=O)CC amlodipine CCOC(=O)C1=C(COCCN)NC(C)=C(C1c1ccccc1Cl)C(=O)OC CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC2=O anthracene c1ccc2cc3ccccc3cc2c1 argatroban CC1CCN(C(C1)C(O)=O)C(=O)C(CCCNC(N)=N)NS(=O)(=O)c 1cccc2CC(C)CNc12 asenapine CN1CC2C(C1)c1cc(Cl)ccc1Oc1ccccc21 atorvastatin CC(C)c1c(C(=O)Nc2ccccc2)c(c(- c2ccc(F)cc2)n1CCC(O)CC(O)CC(O)=O)-c1ccccc1 CCNc1nc(Cl)nc(NC(C)C)n1 azimsulfuron COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2c(cnn2C)- c2nnn(C)n2)n1 azinphos-methyl COP(=S)(OC)SCn1nnc2ccccc2c1=O azoxystrobin COC=C(C(=O)OC)c1ccccc1Oc1cc(Oc2ccccc2C#N)ncn1 balofloxacin CNC1CCCN(C1)c1c(F)cc2c(c1OC)n(cc(C(O)=O)c2=O)C1CC1 basalin CCCN(CCCl)c1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O benoxacor CC1COc2ccccc2N1C(=O)C(Cl)Cl benoxaprofen CC(C(O)=O)c1ccc2oc(nc2c1)-c1ccc(Cl)cc1 bentazone CC(C)N1C(=O)c2ccccc2NS1(=O)=O benzaldehyde O=Cc1ccccc1 benzobicyclon hydrolysate CS(=O)(=O)c1ccc(C(=O)C2=C(O)C3CCC(C3)C2=O)c(Cl)c1 benzoquinone O=C1C=CC(=O)C=C1 bezafibrate CC(C)(Oc1ccc(CCNC(=O)c2ccc(Cl)cc2)cc1)C(O)=O COC(=O)c1cc(Oc2ccc(Cl)cc2Cl)ccc1[N+]([O-])=O bis(4-chlorophenyl) Clc1ccc(Cc2ccc(Cl)cc2)cc1 methane bromacil CCC(C)n1c(=O)[nH]c(C)c(Br)c1=O Oc1c(Br)cc(cc1Br)C#N butamifos CCOP(=S)(NC(C)CC)Oc1cc(C)ccc1[N+]([O-])=O butralin CCC(C)Nc1c(cc(cc1[N+]([O-])=O)C(C)(C)C)[N+]([O-])=O carbamazepine NC(=O)N1c2ccccc2C=Cc2ccccc12 carbaryl CNC(=O)Oc1cccc2ccccc12 carboxin CC1=C(SCCO1)C(=O)Nc1ccccc1 carprofen CC(C(O)=O)c1ccc2c(c1)[nH]c1ccc(Cl)cc21

S23

Name Standardized Smiles cefazolin Cc1nnc(SCC2=C(N3C(SC2)C(NC(=O)Cn2cnnn2)C3=O)C(O)= O)s1 cephalexin CC1=C(N2C(SC1)C(NC(=O)C(N)c1ccccc1)C2=O)C(O)=O cephapirin CC(=O)OCC1=C(N2C(SC1)C(NC(=O)CSc1ccncc1)C2=O)C(O )=O cephradine CC1=C(N2C(SC1)C(NC(=O)C(N)C1=CCC=CC1)C2=O)C(O)= O chloramphenicol OCC(NC(=O)C(Cl)Cl)C(O)c1ccc(cc1)[N+]([O-])=O chlorantraniliprole CNC(=O)c1cc(Cl)cc(C)c1NC(=O)c1cc(Br)nn1-c1ncccc1Cl chlorbromuron CON(C)C(=O)Nc1ccc(Br)c(Cl)c1 chlordimeform CN(C)C=Nc1ccc(Cl)cc1C chlornitrofen [O-][N+](=O)c1ccc(Oc2c(Cl)cc(Cl)cc2Cl)cc1 chlorobenzilate CCOC(=O)C(O)(c1ccc(Cl)cc1)c1ccc(Cl)cc1 chloroxynil Oc1c(Cl)cc(cc1Cl)C#N chlorpropham CC(C)OC(=O)Nc1cccc(Cl)c1 chlortetracycline CN(C)C1C2CC3C(=C(O)C2(O)C(=O)C(C(N)=O)=C1O)C(=O) c1c(O)ccc(Cl)c1C3(C)O cinosulfuron COCCOc1ccccc1S(=O)(=O)NC(=O)Nc1nc(OC)nc(OC)n1 ciprofloxacin OC(=O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O clethodim CCSC(C)CC1CC(O)=C(C(CC)=NOCC=CCl)C(=O)C1 clofibric acid CC(C)(Oc1ccc(Cl)cc1)C(O)=O clothianidin CNC(NCc1cnc(Cl)s1)=N[N+]([O-])=O cyantraniliprole CNC(=O)c1cc(cc(C)c1NC(=O)c1cc(Br)nn1-c1ncccc1Cl)C#N cybutryne CSc1nc(NC2CC2)nc(NC(C)(C)C)n1 cyphenothrin CC(C)=CC1C(C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2)C1(C)C danofloxacin CN1CC2CC1CN2c1cc2n(cc(C(O)=O)c(=O)c2cc1F)C1CC1 dehydroabietic acid CC(C)c1ccc2c(CCC3C(C)(CCCC23C)C(O)=O)c1 desethyl atrazine CC(C)Nc1nc(N)nc(Cl)n1 desipramine CNCCCN1c2ccccc2CCc2ccccc12 desisopropyl atrazine CCNc1nc(N)nc(Cl)n1 diaminostilbene DAS 1 OS(=O)(=O)c1cc(Nc2nc(Nc3ccccc3)nc(n2)N2CCOCC2)ccc1C =Cc1ccc(Nc2nc(Nc3ccccc3)nc(n2)N2CCOCC2)cc1S(O)(=O)= O diaminostilbene DAS 2 OCCN(CCO)c1nc(Nc2ccc(cc2)S(O)(=O)=O)nc(Nc2ccc(C=Cc3 ccc(Nc4nc(Nc5ccc(cc5)S(O)(=O)=O)nc(n4)N(CCO)CCO)cc3S( O)(=O)=O)c(c2)S(O)(=O)=O)n1 diazepam CN1c2ccc(Cl)cc2C(=NCC1=O)c1ccccc1 dibenzothiophene O=s1c2ccccc2c2ccccc12 sulfoxide dichlofluanid CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)c1ccccc1 dichlorophen Oc1ccc(Cl)cc1Cc1cc(Cl)ccc1O CC(Oc1ccc(Cl)cc1Cl)C(O)=O diclofenac OC(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl

S24

Name Standardized Smiles dicloran Nc1c(Cl)cc(cc1Cl)[N+]([O-])=O dicyclanil Nc1nc(NC2CC2)nc(N)c1C#N CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2(O)CC#N diethylene glycol dinitrate [O-][N+](=O)OCCOCCO[N+]([O-])=O diethylstilbestrol CCC(=C(CC)c1ccc(O)cc1)c1ccc(O)cc1 difloxacin CN1CCN(CC1)c1cc2n(cc(C(O)=O)c(=O)c2cc1F)-c1ccc(F)cc1 diflubenzuron Fc1cccc(F)c1C(=O)NC(=O)Nc1ccc(Cl)cc1 dimethyl phosphorothioate COP(=S)(OC)OC diphenylamine N(c1ccccc1)c1ccccc1 distyrylbiphenyl OS(=O)(=O)c1ccccc1C=Cc1ccc(cc1)- disulfonate c1ccc(C=Cc2ccccc2S(O)(=O)=O)cc1 disulfoton CCOP(=S)(OCC)SCCSCC dithianon O=c1c2ccccc2c(=O)c2sc(C#N)c(sc12)C#N diuron CN(C)C(=O)Nc1ccc(Cl)c(Cl)c1 drepamon CCC(C)N(C(C)CC)C(=O)SCc1ccccc1 drepamon sulfoxide CCC(C)N(C(C)CC)C(=O)S(=O)Cc1ccccc1 edifenphos CCOP(=O)(Sc1ccccc1)Sc1ccccc1 emamectin B1A CCC(C)C1OC2(CC3CC(CC=C(C)C(OC4CC(OC)C(OC5CC(O C)C(NC)C(C)O5)C(C)O4)C(C)C=CC=C4COC5C(O)C(C)=CC( C(=O)O3)C45O)O2)C=CC1C enoxacin CCn1cc(C(O)=O)c(=O)c2cc(F)c(nc12)N1CCNCC1 enrofloxacin CCN1CCN(CC1)c1cc2n(cc(C(O)=O)c(=O)c2cc1F)C1CC1 estrone CC12CCC3C(CCc4cc(O)ccc34)C1CCC2=O ethiofencarb CCSCc1ccccc1OC(=O)NC ethyl 5-(2,4- CCOC(=O)c1cc(Oc2ccc(Cl)cc2Cl)ccc1[N+]([O-])=O dichlorophenoxy)-2- nitrobenzoate fenitrothion COP(=S)(OC)Oc1ccc(c(C)c1)[N+]([O-])=O fenofibrate CC(C)OC(=O)C(C)(C)Oc1ccc(cc1)C(=O)c1ccc(Cl)cc1 fenofibric acid CC(C)(Oc1ccc(cc1)C(=O)c1ccc(Cl)cc1)C(O)=O fenoxaprop-p-ethyl CCOC(=O)C(C)Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1 fenpyroximate Cc1nn(C)c(Oc2ccccc2)c1C=NOCc1ccc(cc1)C(=O)OC(C)(C)C fenthion COP(=S)(OC)Oc1ccc(SC)c(C)c1 fenthion sulfoxide COP(=S)(OC)Oc1ccc(c(C)c1)S(C)=O fipronil Nc1c(c(nn1-c1c(Cl)cc(cc1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F fipronil-desulfinyl Nc1c(c(nn1-c1c(Cl)cc(cc1Cl)C(F)(F)F)C#N)C(F)(F)F fipronil-sulfone Nc1c(c(nn1- c1c(Cl)cc(cc1Cl)C(F)(F)F)C#N)S(=O)(=O)C(F)(F)F flavesone CC(C)C(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O florasulam COc1ncc(F)c2nc(nn12)S(=O)(=O)Nc1c(F)cccc1F fluazaindolizine COc1ccc(Cl)c(c1)S(=O)(=O)NC(=O)c1cn2cc(cc(Cl)c2n1)C(F)( F)F

S25

Name Standardized Smiles flufenamic acid OC(=O)c1ccccc1Nc1cccc(c1)C(F)(F)F flumequine CC1CCc2cc(F)cc3c2n1cc(C(O)=O)c3=O flumioxazin Fc1cc2OCC(=O)N(CC#C)c2cc1N1C(=O)C2=C(CCCC2)C1=O flumorph COc1ccc(cc1OC)C(=CC(=O)N1CCOCC1)c1ccc(F)cc1 fluometuron CN(C)C(=O)Nc1cccc(c1)C(F)(F)F fluoxetine CNCCC(Oc1ccc(cc1)C(F)(F)F)c1ccccc1 flutolanil CC(C)Oc1cccc(NC(=O)c2ccccc2C(F)(F)F)c1 fluvastatin CC(C)n1c(C=CC(O)CC(O)CC(O)=O)c(-c2ccc(F)cc2)c2ccccc12 folic acid Nc1nc(=O)c2nc(CNc3ccc(cc3)C(=O)NC(CCC(O)=O)C(O)=O)c nc2[nH]1 furaltadone [O-][N+](=O)c1ccc(C=NN2CC(CN3CCOCC3)OC2=O)o1 furazolidone [O-][N+](=O)c1ccc(C=NN2CCOC2=O)o1 gatifloxacin COc1c(N2CCNC(C)C2)c(F)cc2c1n(cc(C(O)=O)c2=O)C1CC1 gemfibrozil Cc1ccc(C)c(OCCCC(C)(C)C(O)=O)c1 gentisic acid OC(=O)c1cc(O)ccc1O grandiflorone CC1(C)C(=O)C(C(=O)CCc2ccccc2)C(=O)C(C)(C)C1=O hexachlorocyclopentadiene ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl hexahydro-1,3,5-trinitro- [O-][N+](=O)N1CN(CN(C1)[N+]([O-])=O)[N+]([O-])=O 1,3,5-triazine CN(C)c1nc(=O)n(C2CCCCC2)c(=O)n1C hydrochlorothiazide NS(=O)(=O)c1cc2c(NCNS2(=O)=O)cc1Cl hydroxychlorothalonil Oc1c(Cl)c(Cl)c(C#N)c(Cl)c1C#N ibuprofen CC(C)Cc1ccc(cc1)C(C)C(O)=O imazamox COCc1cnc(C2=NC(C)(C(C)C)C(=O)N2)c(c1)C(O)=O CC(C)C1(C)N=C(NC1=O)c1ncc(C)cc1C(O)=O CC(C)C1(C)N=C(NC1=O)c1ncccc1C(O)=O imazaquin CC(C)C1(C)N=C(NC1=O)c1nc2ccccc2cc1C(O)=O imazosulfuron COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2c(Cl)nc3ccccn23)n1 imidacloprid [O-][N+](=O)N=C1NCCN1Cc1ccc(Cl)nc1 indomethacin COc1ccc2n(C(=O)c3ccc(Cl)cc3)c(C)c(CC(O)=O)c2c1 iodosulfuron-methyl COC(=O)c1ccc(I)cc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 iopromide COCC(=O)Nc1c(I)c(C(=O)NCC(O)CO)c(I)c(C(=O)N(C)CC(O) CO)c1I ioxynil Oc1c(I)cc(cc1I)C#N isofenfos CCOP(=S)(NC(C)C)Oc1ccccc1C(=O)OC(C)C isoleptospermone CCC(C)C(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O ketoprofen CC(C(O)=O)c1cccc(c1)C(=O)c1ccccc1 lamotrigine Nc1nnc(c(N)n1)-c1cccc(Cl)c1Cl leptospermone CC(C)CC(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O levothyroxine NC(Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O CON(C)C(=O)Nc1ccc(Cl)c(Cl)c1 lomefloxacin CCn1cc(C(O)=O)c(=O)c2cc(F)c(N3CCNC(C)C3)c(F)c12

S26

Name Standardized Smiles lorazepam OC1N=C(c2ccccc2Cl)c2cc(Cl)ccc2NC1=O m-imazamethabenz-methyl COC(=O)c1cc(C)ccc1C1=NC(C)(C(C)C)C(=O)N1 mandestrobin CNC(=O)C(OC)c1ccccc1COc1cc(C)ccc1C CC(Oc1ccc(Cl)cc1C)C(O)=O CS(=O)(=O)c1ccc(C(=O)C2C(=O)CCCC2=O)c(c1)[N+]([O- ])=O metamitron Cc1nnc(-c2ccccc2)c(=O)n1N methotrexate CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(cc1)C(=O)NC(CCC(O)=O) C(O)=O methyl 2-nitro-5-(2,4,6- COC(=O)c1cc(Oc2c(Cl)cc(Cl)cc2Cl)ccc1[N+]([O-])=O trichlorophenoxy)benzoate methyl 5-(2,4-dichloro-6- COC(=O)c1cc(Oc2c(F)cc(Cl)cc2Cl)ccc1[N+]([O-])=O fluorophenoxy)-2- nitrobenzoate methyl 5-(2-chloro-4- COC(=O)c1cc(Oc2ccc(F)cc2Cl)ccc1[N+]([O-])=O fluorophenoxy)-2- nitrobenzoate metobromuron CON(C)C(=O)Nc1ccc(Br)cc1 metofluthrin COCc1c(F)c(F)c(COC(=O)C2C(C=CC)C2(C)C)c(F)c1F CCc1cccc(C)c1N(C(C)COC)C(=O)CCl metoxuron COc1ccc(NC(=O)N(C)C)cc1Cl metronidazole Cc1ncc(n1CCO)[N+]([O-])=O metsulfuron-methyl COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 midazolam Cc1ncc2CN=C(c3ccccc3F)c3cc(Cl)ccc3-n12 molinate CCSC(=O)N1CCCCCC1 monuron CN(C)C(=O)Nc1ccc(Cl)cc1 musk tibetine Cc1c(C)c(c(c(c1C)[N+]([O-])=O)C(C)(C)C)[N+]([O-])=O myrigalone A CC1=C(O)C(C(=O)CCc2ccccc2)=C(O)C(C)(C)C1=O naphthalen-1-yl O=S(=O)(Oc1cccc2ccccc12)c1ccccc1 benzenesulfonate naphthalene c1ccc2ccccc2c1 naproanilide CC(Oc1ccc2ccccc2c1)C(=O)Nc1ccccc1 napropamide CCN(CC)C(=O)C(C)Oc1cccc2ccccc12 naproxen COc1ccc2cc(ccc2c1)C(C)C(O)=O niclosamide Oc1ccc(Cl)cc1C(=O)Nc1ccc(cc1Cl)[N+]([O-])=O nitenpyram CCN(Cc1ccc(Cl)nc1)C(NC)=C[N+]([O-])=O nithiazine [O-][N+](=O)C=C1NCCCS1 nitrobenzene [O-][N+](=O)c1ccccc1 [O-][N+](=O)c1ccc(Oc2ccc(Cl)cc2Cl)cc1 nitrofuraldehyde [O-][N+](=O)c1ccc(C=O)o1 nitrofurantoin [O-][N+](=O)c1ccc(C=NN2CC(=O)NC2=O)o1 nitroguanidine NC(N)=N[N+]([O-])=O nordiazepam Clc1ccc2NC(=O)CN=C(c3ccccc3)c2c1

S27

Name Standardized Smiles norfloxacin CCn1cc(C(O)=O)c(=O)c2cc(F)c(cc12)N1CCNCC1 octachlorodibenzo-p- Clc1c(Cl)c(Cl)c2Oc3c(Cl)c(Cl)c(Cl)c(Cl)c3Oc2c1Cl dioxin octachlorodibenzofuran Clc1c(Cl)c(Cl)c2c(oc3c(Cl)c(Cl)c(Cl)c(Cl)c23)c1Cl octinoxate CCCCC(CC)COC(=O)C=Cc1ccc(OC)cc1 octyldimethyl PABA CCCCC(CC)COC(=O)c1ccc(cc1)N(C)C ofloxacin CC1COc2c(N3CCN(C)CC3)c(F)cc3c2n1cc(C(O)=O)c3=O oseltamivir CCOC(=O)C1=CC(OC(CC)CC)C(NC(C)=O)C(N)C1 oseltamivir carboxylate CCC(CC)OC1C=C(CC(N)C1NC(C)=O)C(O)=O oxadiazon CC(C)Oc1cc(c(Cl)cc1Cl)-n1nc(oc1=O)C(C)(C)C oxamyl CNC(=O)ON=C(SC)C(=O)N(C)C oxazepam OC1N=C(c2ccccc2)c2cc(Cl)ccc2NC1=O oxyfluorfen CCOc1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1[N+]([O-])=O p-imazamethabenz-methyl COC(=O)c1ccc(C)cc1C1=NC(C)(C(C)C)C(=O)N1 parathion CCOP(=S)(OCC)Oc1ccc(cc1)[N+]([O-])=O parathion-methyl COP(=S)(OC)Oc1ccc(cc1)[N+]([O-])=O CCC(CC)Nc1c(cc(C)c(C)c1[N+]([O-])=O)[N+]([O-])=O penoxsulam COc1cnc(OC)n2nc(NS(=O)(=O)c3c(OCC(F)F)cccc3C(F)(F)F)n c12 pentachlorophenol Oc1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl permethrin CC1(C)C(C=C(Cl)Cl)C1C(=O)OCc1cccc(Oc2ccccc2)c1 phenisopham CCN(C(=O)Oc1cccc(NC(=O)OC(C)C)c1)c1ccccc1 pindolol CC(C)NCC(O)COc1cccc2[nH]ccc12 pirimicarb CN(C)C(=O)Oc1nc(nc(C)c1C)N(C)C preforan [O-][N+](=O)c1ccc(Oc2ccc(cc2[N+]([O-])=O)C(F)(F)F)cc1 profenofos CCCSP(=O)(OCC)Oc1ccc(Br)cc1Cl prometryne CSc1nc(NC(C)C)nc(NC(C)C)n1 CC(C)N(C(=O)CCl)c1ccccc1 CCC(=O)Nc1ccc(Cl)c(Cl)c1 propazine CC(C)Nc1nc(Cl)nc(NC(C)C)n1 propiconazole CCCC1COC(Cn2cncn2)(O1)c1ccc(Cl)cc1Cl propranolol CC(C)NCC(O)COc1cccc2ccccc12 purine-6-sulfinate OS(=O)c1ncnc2nc[nH]c12 pyrene c1cc2ccc3cccc4ccc(c1)c2c34 quinmerac Cc1cnc2c(C(O)=O)c(Cl)ccc2c1 quinoline c1ccc2ncccc2c1 resmethrin CC(C)=CC1C(C(=O)OCc2coc(Cc3ccccc3)c2)C1(C)C rivastigmine CCN(C)C(=O)Oc1cccc(c1)C(C)N(C)C rosuvastatin CC(C)c1nc(nc(- c2ccc(F)cc2)c1C=CC(O)CC(O)CC(O)=O)N(C)S(C)(=O)=O

S28

Name Standardized Smiles salinomycin CCC(C1CCC(C)C(O1)C(C)C(O)C(C)C(=O)C(CC)C1OC2(OC3 (CCC(C)(O3)C3CCC(O)(CC)C(C)O3)C(O)C=C2)C(C)CC1C)C (O)=O sarafloxacin OC(=O)c1cn(-c2ccc(F)cc2)c2cc(N3CCNCC3)c(F)cc2c1=O sulcotrione CS(=O)(=O)c1ccc(C(=O)C2C(=O)CCCC2=O)c(Cl)c1 sulfachloropyridazine Nc1ccc(cc1)S(=O)(=O)Nc1ccc(Cl)nn1 sulfadiazine Nc1ccc(cc1)S(=O)(=O)Nc1ncccn1 sulfadimethoxine COc1cc(NS(=O)(=O)c2ccc(N)cc2)nc(OC)n1 sulfamerazine Cc1ccnc(NS(=O)(=O)c2ccc(N)cc2)n1 sulfamethazine Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1 sulfamethizole Cc1nnc(NS(=O)(=O)c2ccc(N)cc2)s1 sulfamethoxazole Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1 sulfamethoxazole Cc1cc(no1)N(C1OC(C(O)C(O)C1O)C(O)=O)S(=O)(=O)c1ccc( glucuronide N)cc1 sulfathiazole Nc1ccc(cc1)S(=O)(=O)Nc1nccs1 sulfisoxazole Cc1noc(NS(=O)(=O)c2ccc(N)cc2)c1C sulprofos CCCSP(=S)(OCC)Oc1ccc(SC)cc1 tadalafil CN1CC(=O)N2C(Cc3c([nH]c4ccccc34)C2c2ccc3OCOc3c2)C1 =O tamoxifen CCC(=C(c1ccccc1)c1ccc(OCCN(C)C)cc1)c1ccccc1 temazepam CN1c2ccc(Cl)cc2C(=NC(O)C1=O)c1ccccc1 CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC2O tetrachlorocatechol Oc1c(O)c(Cl)c(Cl)c(Cl)c1Cl tetrachlorohydroquinone Oc1c(Cl)c(Cl)c(O)c(Cl)c1Cl tetrachlororesorcinol Oc1c(Cl)c(O)c(Cl)c(Cl)c1Cl tetracycline CN(C)C1C2CC3C(=C(O)C2(O)C(=O)C(C(N)=O)=C1O)C(=O) c1c(O)cccc1C3(C)O thiamethoxam CN1COCN(Cc2cnc(Cl)s2)C1=N[N+]([O-])=O thifensulfuron-methyl COC(=O)c1sccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 thioanisole CSc1ccccc1 thiobencarb CCN(CC)C(=O)SCc1ccc(Cl)cc1 timolol CC(C)(C)NCC(O)COc1nsnc1N1CCOCC1 trazodone Clc1cccc(c1)N1CCN(CCCn2nc3ccccn3c2=O)CC1 CC12C=CC3=C4CCC(=O)C=C4CCC3C1CCC2O trendione CC12C=CC3=C4CCC(=O)C=C4CCC3C1CCC2=O triasulfuron COc1nc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2OCCCl)n1 OC(=O)COc1nc(Cl)c(Cl)cc1Cl triclosan Oc1cc(Cl)ccc1Oc1ccc(Cl)cc1Cl CCCN(CCC)c1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O trimethoprim COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC valerophenone CCCCC(=O)c1ccccc1 77

S29

78 List S2. Complete list of compound names and standardized smiles in DB-EFSA-ENV.

Name Standardized Smiles 1- OC(=O)Cc1cccc2ccccc12 naphthaleneacetic acid 2,4- OC(=O)COc1ccc(Cl)cc1Cl dichlorophenoxya cetic acid 2,4- CCCCC(CC)COC(=O)COc1ccc(Cl)cc1Cl dichlorophenoxya cetic acid 2- ethylhexyl ester 6- Clc1ccc2[nH]c(=O)oc2c1 chlorobenzoxazol on acequinocyl CCCCCCCCCCCCC1=C(OC(C)=O)C(=O)c2ccccc2C1=O acrinathrin CC1(C)C(C=CC(=O)OC(C(F)(F)F)C(F)(F)F)C1C(=O)OC(C#N)c1cccc(Oc2cccc c2)c1 Nc1cc(Cl)nc(C(O)=O)c1Cl amisulbrom CN(C)S(=O)(=O)n1cnc(n1)S(=O)(=O)n1c(C)c(Br)c2ccc(F)cc12 CCCCN(CC)c1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O benfuracarb CCOC(=O)CCN(SN(C)C(=O)Oc1cccc2CC(C)(C)Oc12)C(C)C bensulfuron- COc1cc(OC)nc(NC(=O)NS(=O)(=O)Cc2ccccc2C(O)=O)n1 methyl bentazone CC(C)N1C(=O)c2ccccc2NS1(=O)=O benzovindiflupyr Cn1cc(C(=O)Nc2cccc3C4CCC(C4=C(Cl)Cl)c23)c(n1)C(F)F bifenox COC(=O)c1cc(Oc2ccc(Cl)cc2Cl)ccc1[N+]([O-])=O bifenthrin Cc1c(COC(=O)C2C(C=C(Cl)C(F)(F)F)C2(C)C)cccc1-c1ccccc1 bitertanol CC(C)(C)C(O)C(Oc1ccc(cc1)-c1ccccc1)n1cncn1 bupirimate CCCCc1c(C)nc(NCC)nc1OS(=O)(=O)N(C)C buprofezin CC(C)N1C(SCN(C1=O)c1ccccc1)=NC(C)(C)C butralin CCC(C)Nc1c(cc(cc1[N+]([O-])=O)C(C)(C)C)[N+]([O-])=O carboxin CC1=C(SCCO1)C(=O)Nc1ccccc1 chlorantraniliprole CNC(=O)c1cc(Cl)cc(C)c1NC(=O)c1cc(Br)nn1-c1ncccc1Cl cyantraniliprole CNC(=O)c1cc(cc(C)c1NC(=O)c1cc(Br)nn1-c1ncccc1Cl)C#N cyflumetofen COCCOC(=O)CC(C#N)(C(=O)c1ccccc1C(F)(F)F)c1ccc(cc1)C(C)(C)C cyhalofop-butyl CCCCOC(=O)C(C)Oc1ccc(Oc2ccc(cc2F)C#N)cc1 cyhalothrin CC1(C)C(C=C(Cl)C(F)(F)F)C1C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1 cypermethrin CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1 cyprodinil CGA Cc1cc(nc(Nc2cccc(O)c2)n1)C1CC1 275535 desethyl CC(C)(C)Nc1nc(N)nc(Cl)n1 dichlorprop CC(Oc1ccc(Cl)cc1Cl)C(O)=O diclofop CC(Oc1ccc(Oc2ccc(Cl)cc2Cl)cc1)C(O)=O

S30

Name Standardized Smiles diclofop-methyl COC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2Cl)cc1 diethofencarb CCOc1ccc(NC(=O)OC(C)C)cc1OCC diflufenican Fc1ccc(NC(=O)c2cccnc2Oc2cccc(c2)C(F)(F)F)c(F)c1 COCC(C)N(C(=O)CCl)c1c(C)csc1C dimethomorph COc1ccc(cc1OC)C(=CC(=O)N1CCOCC1)c1ccc(Cl)cc1 dimoxystrobin CNC(=O)C(=NOC)c1ccccc1COc1cc(C)ccc1C diphenylamine N(c1ccccc1)c1ccccc1 dithianon O=c1c2ccccc2c(=O)c2sc(C#N)c(sc12)C#N emamectin B1A CCC(C)C1OC2(CC3CC(CC=C(C)C(OC4CC(OC)C(OC5CC(OC)C(NC)C(C)O5) C(C)O4)C(C)C=CC=C4COC5C(O)C(C)=CC(C(=O)O3)C45O)O2)C=CC1C ethalfluralin CCN(CC(C)=C)c1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O ethirimol CCCCc1c(C)nc(NCC)nc1O etofenprox CCOc1ccc(cc1)C(C)(C)COCc1cccc(Oc2ccccc2)c1 fenamiphos CCOP(=O)(NC(C)C)Oc1ccc(SC)c(C)c1 fenazaquin CC(C)(C)c1ccc(CCOc2ncnc3ccccc23)cc1 fenitrothion COP(=S)(OC)Oc1ccc(c(C)c1)[N+]([O-])=O fenoxaprop-p- CCOC(=O)C(C)Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1 ethyl fenoxycarb CCOC(=O)NCCOc1ccc(Oc2ccccc2)cc1 fenpyrazamine CC(C)n1n(C(=O)SCC=C)c(N)c(-c2ccccc2C)c1=O fenpyroximate Cc1nn(C)c(Oc2ccccc2)c1C=NOCc1ccc(cc1)C(=O)OC(C)(C)C fenvalerate CC(C)C(C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1)c1ccc(Cl)cc1 fipronil Nc1c(c(nn1-c1c(Cl)cc(cc1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F florasulam COc1ncc(F)c2nc(nn12)S(=O)(=O)Nc1c(F)cccc1F -p-butyl CCCCOC(=O)C(C)Oc1ccc(Oc2ccc(cn2)C(F)(F)F)cc1 fluazinam [O-][N+](=O)c1cc(c(Cl)c(c1Nc1ncc(cc1Cl)C(F)(F)F)[N+]([O-])=O)C(F)(F)F fludioxonil FC1(F)Oc2cccc(c2O1)-c1c[nH]cc1C#N flufenoxuron Fc1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1NC(=O)NC(=O)c1c(F)cccc1F flufenoxuron Nc1ccc(Oc2ccc(cc2Cl)C(F)(F)F)cc1F 241208 flumetralin CCN(Cc1c(F)cccc1Cl)c1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O flumioxazin Fc1cc2OCC(=O)N(CC#C)c2cc1N1C(=O)C2=C(CCCC2)C1=O fluopicolide FC(F)(F)c1cnc(CNC(=O)c2c(Cl)cccc2Cl)c(Cl)c1 fluoxastrobin CON=C(C1=NOCCO1)c1ccccc1Oc1ncnc(Oc2ccccc2Cl)c1F flupyradifurone FC(F)CN(Cc1ccc(Cl)nc1)C1=CC(=O)OC1 fluquinconazole- Fc1ccc2[nH]c(=O)n(-c3ccc(Cl)cc3Cl)c(=O)c2c1 dione flurochloridone FC(F)(F)c1cccc(c1)N1CC(CCl)C(Cl)C1=O flurprimidol CC(C)C(O)(c1ccc(OC(F)(F)F)cc1)c1cncnc1 flutianil COc1ccccc1N1CCSC1=C(Sc1cc(ccc1F)C(F)(F)F)C#N formetanate CNC(=O)Oc1cccc(c1)N=CN(C)C fuberidazole c1coc(c1)-c1nc2ccccc2[nH]1 halauxifen-metyhl COC(=O)c1nc(cc(N)c1Cl)-c1ccc(Cl)c(OC)c1F

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Name Standardized Smiles haloxyfop-P COC(=O)C(C)Oc1ccc(Oc2ncc(cc2Cl)C(F)(F)F)cc1 haloxyfop-P-acid CC(Oc1ccc(Oc2ncc(cc2Cl)C(F)(F)F)cc1)C(O)=O hexythiazox CC1C(SC(=O)N1C(=O)NC1CCCCC1)c1ccc(Cl)cc1 imazaquin CC(C)C1(C)N=C(NC1=O)c1nc2ccccc2cc1C(O)=O imidacloprid [O-][N+](=O)N=C1NCCN1Cc1ccc(Cl)nc1 isoproturon CC(C)c1ccc(NC(=O)N(C)C)cc1 isopyrazam CC(C)C1C2CCC1c1c2cccc1NC(=O)c1cn(C)nc1C(F)F isoxaben CCC(C)(CC)c1cc(NC(=O)c2c(OC)cccc2OC)on1 lufenuron FC(C(F)(F)F)C(F)(F)Oc1cc(Cl)c(NC(=O)NC(=O)c2c(F)cccc2F)cc1Cl mandestrobin CNC(=O)C(OC)c1ccccc1COc1cc(C)ccc1C mandipropamid COc1cc(CCNC(=O)C(OCC#C)c2ccc(Cl)cc2)ccc1OCC#C meptyldinocap CCCCCCC(C)c1cc(cc(c1OC(=O)C=CC)[N+]([O-])=O)[N+]([O-])=O metaflumizone FC(F)(F)Oc1ccc(NC(=O)NN=C(Cc2ccc(cc2)C#N)c2cccc(c2)C(F)(F)F)cc1 metamitron Cc1nnc(-c2ccccc2)c(=O)n1N metconazole CC1(C)CCC(Cc2ccc(Cl)cc2)C1(O)Cn1cncn1 CNC(=O)Oc1cc(C)c(SC)c(C)c1 metobromuron CON(C)C(=O)Nc1ccc(Br)cc1 metrafenone COc1ccc(Br)c(C)c1C(=O)c1c(C)cc(OC)c(OC)c1OC CSc1nnc(c(=O)n1N)C(C)(C)C metsulfuron- COC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1 methyl napropamide CCN(CC)C(=O)C(C)Oc1cccc2ccccc12 novaluron FC(OC(F)(F)F)C(F)(F)Oc1ccc(NC(=O)NC(=O)c2c(F)cccc2F)cc1Cl oryzalin CCCN(CCC)c1c(cc(cc1[N+]([O-])=O)S(N)(=O)=O)[N+]([O-])=O oxadiazon CC(C)Oc1cc(c(Cl)cc1Cl)-n1nc(oc1=O)C(C)(C)C oxyfluorfen CCOc1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1[N+]([O-])=O penoxsulam COc1cnc(OC)n2nc(NS(=O)(=O)c3c(OCC(F)F)cccc3C(F)(F)F)nc12 phosalone CCOP(=S)(OCC)SCn1c2ccc(Cl)cc2oc1=O phosmet COP(=S)(OC)SCN1C(=O)c2ccccc2C1=O Nc1c(Cl)c(Cl)nc(C(O)=O)c1Cl picloram NOA CCc1cc(C)cc(CC)c1C1(O)C(=O)N2CCOCCN2C1=O 447204 pinoxaden CCc1cc(C)cc(CC)c1-c1c(OC(=O)C(C)(C)C)n2CCOCCn2c1=O pirimicarb CN(C)C(=O)Oc1nc(nc(C)c1C)N(C)C pirimiphos-methyl CCN(CC)c1nc(C)cc(OP(=S)(OC)OC)n1 CCCN(CCOc1c(Cl)cc(Cl)cc1Cl)C(=O)n1ccnc1 prohexadione CCC(=O)C1C(=O)CC(CC1=O)C(O)=O propaquizafop CC(Oc1ccc(Oc2cnc3cc(Cl)ccc3n2)cc1)C(=O)OCCON=C(C)C propargite CC(C)(C)c1ccc(OC2CCCCC2OS(=O)OCC#C)cc1 proquinazid CCCOc1nc2ccc(I)cc2c(=O)n1CCC prothioconazole OC(Cc1ccccc1Cl)(Cn1nc[nH]c1=S)C1(Cl)CC1 pymetrozine CC1=NNC(=O)N(C1)N=Cc1cccnc1

S32

Name Standardized Smiles pyraflufen-ethyl CCOC(=O)COc1cc(-c2nn(C)c(OC(F)F)c2Cl)c(F)cc1Cl pyridaben CC(C)(C)c1ccc(CSc2cnn(c(=O)c2Cl)C(C)(C)C)cc1 pyridafol Oc1cc(Cl)nnc1-c1ccccc1 pyridate CCCCCCCCSC(=O)Oc1cc(Cl)nnc1-c1ccccc1 pyriproxyfen CC(COc1ccc(Oc2ccccc2)cc1)Oc1ccccn1 pyroxsulam COc1cc(OC)n2nc(NS(=O)(=O)c3c(OC)nccc3C(F)(F)F)nc2n1 quinmerac Cc1cnc2c(C(O)=O)c(Cl)ccc2c1 quizalofop-p-ethyl CCOC(=O)C(C)Oc1ccc(Oc2cnc3cc(Cl)ccc3n2)cc1 quizalofop-p- CC(Oc1ccc(Oc2cnc3cc(Cl)ccc3n2)cc1)C(=O)OCC1CCCO1 tefuryl rimsulfuron CCS(=O)(=O)c1cccnc1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 sedaxane Cn1cc(C(=O)Nc2ccccc2C2CC2C2CC2)c(n1)C(F)F spiromesifen Cc1cc(C)c(C2=C(OC(=O)CC(C)(C)C)C3(CCCC3)OC2=O)c(C)c1 spirotetramat CCOC(=O)OC1=C(C(=O)NC11CCC(CC1)OC)c1cc(C)ccc1C sulcotrione CS(=O)(=O)c1ccc(C(=O)C2C(=O)CCCC2=O)c(Cl)c1 sulfosulfuron CCS(=O)(=O)c1nc2ccccn2c1S(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1 sulfoxaflor CC(c1ccc(nc1)C(F)(F)F)S(C)(=O)=NC#N sulfoxaflor CC(c1ccc(nc1)C(F)(F)F)S(C)(=O)=NC(N)=O X11719474 teflubenzuron Fc1cccc(F)c1C(=O)NC(=O)Nc1cc(Cl)c(F)c(Cl)c1F tembotrione CS(=O)(=O)c1ccc(C(=O)C2C(=O)CCCC2=O)c(Cl)c1COCC(F)(F)F terbuthylazine CCNc1nc(Cl)nc(NC(C)(C)C)n1 thiencarbazone- COC(=O)c1csc(C)c1S(=O)(=O)NC(=O)n1nc(OC)n(C)c1=O methyl tralkoxydim CCON=C(CC)C1C(=O)CC(CC1=O)c1c(C)cc(C)cc1C triazoxide [O-][n+]1nc(nc2ccc(Cl)cc12)-n1ccnc1 triclopyr OC(=O)COc1nc(Cl)c(Cl)cc1Cl triclopyr CCCCOCCOC(=O)COc1nc(Cl)c(Cl)cc1Cl butoxyethyl ester triflumizole CCCOCC(=Nc1ccc(Cl)cc1C(F)(F)F)n1ccnc1 triflumuron FC(F)(F)Oc1ccc(NC(=O)NC(=O)c2ccccc2Cl)cc1 trifluralin CCCN(CCC)c1c(cc(cc1[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O triflusulfuron- COC(=O)c1cccc(C)c1S(=O)(=O)NC(=O)Nc1nc(OCC(F)(F)F)nc(n1)N(C)C methyl 79

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80 References

81 1. Armbrust, K. L., Photodegradation of hydroxychlorothalonil in aqueous solutions. 82 Environ. Toxicol. Chem. 2001, 20 (12), 2699-2703. 83 2. Hawari, J.; Halasz, A.; Groom, C.; Deschamps, S.; Paquet, L.; Beaulieu, C.; Corriveau, 84 A., Photodegradation of rdx in aqueous solution: A mechanistic probe for biodegradation with 85 rhodococcus sp. Environ. Sci. Technol. 2002, 36 (23), 5117-5123. 86 3. Just, C. L.; Schnoor, J. L., Phytophotolysis of hexahydro-1,3,5-trinitro-1,3,5-triazine 87 (rdx) in leaves of reed canary grass. Environ. Sci. Technol. 2004, 38 (1), 290-295. 88

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