Fuzzy Comprehensive Evaluation Assistant 3D-QSAR of Environmentally Friendly FQs to Reduce ADRs
Abstract
:1. Introduction
2. Materials and Methods
2.1. Characterization of the ADRs of FQs
2.2. Construction of a 3D-QSAR Model Using the Fuzzy CEI of ADRs of FQs
2.2.1. Construction of a Fuzzy Comprehensive Evaluation System for ADRs of FQs
2.2.2. Structure Optimization and Superposition of FQ Molecules
2.2.3. Construction of a 3D-QSAR Model Using Multiple ADRs of FQs
2.3. Feasibility of Molecular Modification of FQs and Stability Evaluation of the Derivatives
3. Results and Discussion
3.1. Comprehensive Evaluation of the Three ADR Indicators of FQs
3.2. Construction and Evaluation of the 3D-QSAR Model for ADRs of FQs Using the Fuzzy CEI
3.2.1. Analysis and Evaluation of the FQs CoMFA Model
3.2.2. Validation of the FQs CoMFA Model
3.3. Determination of Single and Double Substitution Sites and Substituent Groups of FQ Derivatives Using Contour Maps
3.4. Comprehensive Evaluation, Persistent Organic Pollutant Characteristics, and Stability Evaluations of FQ Derivatives with Three Common ADRs
3.4.1. Fuzzy Comprehensive Evaluation of FQ Derivatives and Three Common ADRs
3.4.2. Evaluation of the Persistent Organic Pollutant Characteristics of FQ Derivatives
3.4.3. Single-Factor Validation of the ADRs of the FQ Derivatives
3.4.4. Stability Evaluation of FQ Derivatives
3.5. Risk Assessment of FQ Derivatives
3.5.1. Human Health Risk Assessment of FQ Derivatives at Median Lethal Concentrations in Water
3.5.2. Risk Assessment of the Genotoxicities of Disinfection By-Products of the FQ Derivatives
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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No. | Compounds | Docking Results | CEI | ||
---|---|---|---|---|---|
3IP9 | 3N8V | 2L0W | |||
1 | Difloxacin | 62.686 | 97.120 | 65.403 | 0.687 |
2 | Enrofloxacin | 64.070 | 90.401 | 90.476 | 0.707 |
3 | Norfloxacin | 58.422 | 90.557 | 88.709 | 0.601 |
4 | Lomefloxacin | 68.236 | 91.137 | 80.276 | 0.762 |
5 | Ofloxacin | 66.638 | 86.122 | 86.940 | 0.697 |
6 | Pefloxacin | 57.529 | 99.215 | 92.037 | 0.689 |
7 | Fleroxacin | 66.948 | 99.890 | 83.403 | 0.843 |
8 | Ciprofloxacin | 60.930 | 92.373 | 86.780 | 0.661 |
9 | Bal ofloxacin | 49.203 | 71.254 | 56.908 | 0.137 |
10 | Marbofloxacin | 65.300 | 95.242 | 88.670 | 0.777 |
11 | Pipemidic acid | 62.866 | 97.025 | 89.229 | 0.754 |
12 | Cinoxacin | 55.950 | 90.199 | 85.239 | 0.543 |
13 | Enoxacin | 60.660 | 86.605 | 87.601 | 0.596 |
14 | Danofloxacin | 67.775 | 91.772 | 93.715 | 0.797 |
15 | Gatifloxacin | 53.617 | 63.247 | 64.941 | 0.152 |
16 | Levofloxacin | 66.638 | 86.122 | 86.940 | 0.697 |
17 | Rufloxacin | 62.386 | 70.009 | 76.275 | 0.415 |
18 | Pazufloxacin | 74.075 | 94.849 | 86.206 | 0.925 |
19 | Nadifloxacin | 56.928 | 82.392 | 73.634 | 0.444 |
20 | Moxifloxacin | 46.442 | 73.108 | 73.101 | 0.152 |
21 | Sparfloxacin | 60.872 | 84.400 | 85.512 | 0.570 |
22 | Sarafloxacin | 59.595 | 82.206 | 72.443 | 0.487 |
23 | Amifloxacin | 59.512 | 86.682 | 80.072 | 0.555 |
24 | Besifloxacin | 55.541 | 79.981 | 76.735 | 0.401 |
25 | Clinafloxacin | 59.317 | 86.327 | 80.656 | 0.549 |
26 | Grepafloxacin | 66.245 | 90.285 | 93.474 | 0.753 |
27 | Orbifloxacin | 62.945 | 81.585 | 84.843 | 0.575 |
28 | Sitafloxacin | 60.702 | 72.267 | 83.135 | 0.428 |
29 | Temafloxacin | 66.934 | 88.733 | 75.241 | 0.699 |
Model | q2 | n | SEE | r2 | F | SEP | Q2ext | cSDEP | dq2/dr2yy | r2pred |
---|---|---|---|---|---|---|---|---|---|---|
CoMFA | 0.560 | 10 | 0.007 | 0.999 | 1892.254 | 0.215 | 0.999 | 0.246 | 1.861 | 0.692 |
No. | Compounds | CEI | Pred. | Residuals |
---|---|---|---|---|
1 | Difloxacinb | 0.687 | 0.688 | 0.18% |
2 | Enrofloxacina | 0.707 | 0.706 | 0.08% |
3 | Norfloxacina | 0.601 | 0.618 | 2.78% |
4 | Lomefloxacina | 0.762 | 0.756 | 0.82% |
5 | Ofloxacina | 0.697 | 0.702 | 0.76% |
6 | Pefloxacina | 0.689 | 0.686 | 0.39% |
7 | Fleroxacina | 0.843 | 0.846 | 0.35% |
8 | Ciprofloxacina | 0.661 | 0.663 | 0.26% |
9 | Balofloxacina | 0.137 | 0.140 | 1.92% |
10 | Marbofloxacina | 0.777 | 0.782 | 0.67% |
11 | Pipemidic acida | 0.754 | 0.751 | 0.36% |
12 | Cinoxacina | 0.543 | 0.542 | 0.23% |
13 | Enoxacina | 0.596 | 0.587 | 1.45% |
14 | Danofloxacina | 0.797 | 0.794 | 0.42% |
15 | Gatifloxacina | 0.152 | 0.149 | 1.74% |
16 | Levofloxacina | 0.697 | 0.700 | 0.47% |
17 | Rufloxacina | 0.415 | 0.417 | 0.50% |
18 | Pazufloxacina b | 0.925 | 0.922 | 0.28% |
19 | Nadifloxacina | 0.444 | 0.442 | 0.49% |
20 | Moxifloxacina | 0.152 | 0.152 | 0.23% |
21 | Sparfloxacina | 0.570 | 0.568 | 0.30% |
22 | Sarafloxacinb | 0.487 | 0.471 | 3.31% |
23 | Amifloxacinb | 0.555 | 0.554 | 0.22% |
24 | Besifloxacina | 0.401 | 0.327 | 18.49% |
25 | Clinafloxacinb | 0.549 | 0.415 | 24.47% |
26 | Grepafloxacinb | 0.753 | 0.544 | 27.74% |
27 | Orbifloxacina | 0.575 | 0.570 | 0.82% |
28 | Sitafloxacinb | 0.428 | 0.462 | 8.01% |
29 | Temafloxacinb | 0.699 | 0.676 | 3.26% |
Compounds | Structure | CEI | |
---|---|---|---|
Pred. | Relative Error | ||
No.18 | PAZ | 0.925 | - |
Derivative-1 | 1-Methyl-PAZ | 0.619 | −33.08% |
Derivative-2 | 1-Hydrogen-PAZ | 0.578 | −37.51% |
Derivative-3 | 1-Ethyl-PAZ | 0.649 | −29.84% |
Derivative-4 | 1-Vinyl-PAZ | 0.660 | −28.65% |
Derivative-5 | 1-Ethynyl-PAZ | 0.719 | −22.27% |
Derivative-6 | 1-Carbonyl-PAZ | 0.792 | −14.38% |
Derivative-7 | 5-Hydroxyl-PAZ | 0.879 | −4.97% |
Derivative-8 | 5-Carboxyl-PAZ | 0.827 | −10.59% |
Derivative-9 | 5-Sulfur-PAZ | 0.848 | −8.32% |
Derivative-10 | 5-Fluorine-PAZ | 0.814 | −12.00% |
Derivative-11 | 5-Chlorine-PAZ | 0.717 | −22.49% |
Derivative-12 | 5-Bromine-PAZ | 0.726 | −21.51% |
Derivative-13 | 1-Methyl-5-Hydroxyl-PAZ | 0.762 | −17.62% |
Derivative-14 | 1-Methyl-5-Carboxyl-PAZ | 0.743 | −19.68% |
Derivative-15 | 1-Methyl-5-Sulfur-PAZ | 0.778 | −15.89% |
Derivative-16 | 1-Methyl-5-Fluorine-PAZ | 0.715 | −22.70% |
Derivative-17 | 1-Methyl-Chlorine-PAZ | 0.743 | −19.68% |
Derivative-18 | 1-Methyl-5-Bromine-PAZ | 0.775 | −16.22% |
Derivative-19 | 1-Hydrogen-5-Hydroxyl-PAZ | 0.652 | −29.51% |
Derivative-20 | 1-Hydrogen-5-Carboxyl-PAZ | 0.592 | −36.00% |
Derivative-21 | 1-Hydrogen-5-Sulfur-PAZ | 0.641 | −30.70% |
Derivative-22 | 1-Hydrogen-5-Fluorine-PAZ | 0.549 | −40.65% |
Derivative-23 | 1-Hydrogen-Chlorine-PAZ | 0.637 | −31.14% |
Derivative-24 | 1-Hydrogen-5-Bromine-PAZ | 0.659 | −28.76% |
Derivative-25 | 1-Ethyl-5-Hydroxyl-PAZ | 0.754 | −18.49% |
Derivative-26 | 1-Ethyl-5-Carboxyl-PAZ | 0.796 | −13.95% |
Derivative-27 | 1-Ethyl-5-Sulfur-PAZ | 0.776 | −16.11% |
Derivative-28 | 1-Ethyl-5-Fluorine-PAZ | 0.727 | −21.41% |
Derivative-29 | 1-Ethyl-Chlorine-PAZ | 0.828 | −10.49% |
Derivative-30 | 1-Ethyl-5-Bromine-PAZ | 0.732 | −20.86% |
Derivative-31 | 1-Vinyl-5-Hydroxyl-PAZ | 0.677 | −26.81% |
Derivative-32 | 1-Vinyl-5-Carboxyl-PAZ | 0.613 | −33.73% |
Derivative-33 | 1-Vinyl-5-Sulfur-PAZ | 0.710 | −23.24% |
Derivative-34 | 1-Vinyl-5-Fluorine-PAZ | 0.691 | −25.30% |
Derivative-35 | 1-Vinyl-5-Chlorine-PAZ | 0.558 | −39.68% |
Derivative-36 | 1-Vinyl-5-Bromine-PAZ | 0.454 | −50.92% |
Derivative-37 | 1-Ethynyl-5-Hydroxyl-PAZ | 0.659 | −28.76% |
Derivative-38 | 1-Ethynyl-5-Carboxyl-PAZ | 0.880 | −4.86% |
Derivative-39 | 1-Ethynyl-5-Sulfur-PAZ | 0.875 | −5.41% |
Derivative-40 | 1-Ethynyl-5-Fluorine-PAZ | 0.742 | −19.78% |
Derivative-41 | 1- Ethynyl-5-Chlorine-PAZ | 0.800 | −13.51% |
Derivative-42 | 1-Ethynyl-5-Bromine-PAZ | 0.636 | −31.24% |
Derivative-43 | 1-Carbonyl-5-Hydroxyl-PAZ | 0.718 | −22.38% |
Derivative-44 | 1-Carbonyl-5-Carboxyl-PAZ | 0.682 | −26.27% |
Derivative-45 | 1-Carbonyl-5-Sulfur-PAZ | 0.574 | −37.95% |
Derivative-46 | 1-Carbonyl-5-Fluorine-PAZ | 0.600 | −35.14% |
Derivative-47 | 1-Carbonyl-5-Chlorine-PAZ | 0.758 | −18.05% |
Derivative-48 | 1-Carbonyl-5-Bromine-PAZ | 0.633 | −31.57% |
Compounds | pLOEC (Pred. AVG) * | logt1/2 | logKow | |||
---|---|---|---|---|---|---|
Pred. | Relative Error | Pred. | Relative Error | Pred. | Relative Error | |
PAZ | 7.048 | - | 1.789 | - | 1.140 | - |
Derivative-1 | 7.404 | 5.05% | 1.925 | 7.60% | 0.191 | −83.25% |
Derivative-2 | 7.575 | 7.48% | 1.954 | 9.22% | 0.140 | −87.72% |
Derivative-3 | 7.322 | 3.89% | 1.937 | 8.27% | 0.289 | −74.65% |
Derivative-4 | 6.930 | −1.67% | 1.934 | 8.11% | 1.689 | 48.16% |
Derivative-5 | 6.936 | −1.59% | 1.869 | 4.47% | 1.602 | 40.53% |
Derivative-6 | 6.777 | −3.85% | 1.926 | 7.66% | 1.254 | 10.00% |
Derivative-7 | 7.082 | 0.48% | 1.726 | −3.52% | 1.169 | 2.54% |
Derivative-8 | 7.203 | 2.20% | 1.821 | 1.79% | 1.631 | 43.07% |
Derivative-9 | 7.073 | 0.35% | 1.728 | −3.41% | 1.354 | 18.77% |
Derivative-10 | 7.089 | 0.58% | 1.744 | −2.52% | 1.113 | −2.37% |
Derivative-11 | 7.031 | −0.24% | 1.732 | −3.19% | 1.170 | 2.63% |
Derivative-12 | 7.033 | −0.21% | 1.954 | 9.22% | 1.126 | −1.23% |
Derivative-13 | 7.022 | −0.37% | 1.827 | 2.12% | 1.856 | 62.81% |
Derivative-14 | 7.009 | −0.55% | 1.555 | −13.08% | 2.623 | 130.09% |
Derivative-15 | 7.048 | 0.00% | 1.987 | 11.07% | 2.083 | 82.72% |
Derivative-16 | 7.061 | 0.18% | 1.831 | 2.35% | 1.848 | 62.11% |
Derivative-17 | 6.993 | −0.78% | 1.930 | 7.88% | 1.907 | 67.28% |
Derivative-18 | 7.007 | −0.58% | 1.862 | 4.08% | 2.102 | 84.39% |
Derivative-19 | 7.193 | 2.06% | 1.860 | 3.97% | 1.629 | 42.89% |
Derivative-20 | 7.245 | 2.80% | 1.942 | 8.55% | 2.108 | 84.91% |
Derivative-21 | 7.185 | 1.94% | 1.862 | 4.08% | 1.794 | 57.37% |
Derivative-22 | 7.129 | 1.15% | 1.952 | 9.11% | 1.768 | 55.09% |
Derivative-23 | 7.121 | 1.04% | 1.969 | 10.06% | 1.545 | 35.53% |
Derivative-24 | 7.173 | 1.77% | 1.877 | 4.92% | 1.639 | 43.77% |
Derivative-25 | 7.030 | −0.26% | 2.028 | 13.36% | 2.055 | 80.26% |
Derivative-26 | 7.034 | −0.20% | 2.073 | 15.87% | 2.254 | 97.72% |
Derivative-27 | 7.051 | 0.04% | 1.978 | 10.56% | 2.087 | 83.07% |
Derivative-28 | 7.033 | −0.21% | 1.837 | 2.68% | 1.875 | 64.47% |
Derivative-29 | 6.988 | −0.85% | 1.956 | 9.33% | 2.085 | 82.89% |
Derivative-30 | 7.055 | 0.10% | 1.847 | 3.24% | 1.917 | 68.16% |
Derivative-31 | 6.987 | −0.87% | 1.903 | 6.37% | 2.317 | 103.25% |
Derivative-32 | 6.938 | −1.56% | 1.414 | −20.96% | 2.378 | 108.60% |
Derivative-33 | 6.743 | −4.33% | 1.769 | −1.12% | 2.599 | 127.98% |
Derivative-34 | 7.253 | 2.91% | 1.438 | −19.62% | 0.486 | −57.37% |
Derivative-35 | 7.242 | 2.75% | 1.941 | 8.50% | 2.403 | 110.79% |
Derivative-36 | 7.293 | 3.48% | 1.939 | 8.38% | 2.330 | 104.39% |
Derivative-37 | 7.123 | 1.06% | 1.884 | 5.31% | 2.205 | 93.42% |
Derivative-38 | 6.949 | −1.40% | 1.709 | −4.47% | 2.515 | 120.61% |
Derivative-39 | 6.922 | −1.79% | 2.060 | 15.15% | 2.352 | 106.32% |
Derivative-40 | 6.884 | −2.33% | 1.749 | −2.24% | 2.215 | 94.30% |
Derivative-41 | 7.056 | 0.11% | 1.854 | 3.63% | 1.959 | 71.84% |
Derivative-42 | 7.076 | 0.40% | 1.942 | 8.55% | 2.184 | 91.58% |
Derivative-43 | 7.180 | 1.87% | 1.880 | 5.09% | 1.580 | 38.60% |
Derivative-44 | 7.057 | 0.13% | 1.870 | 4.53% | 1.960 | 71.93% |
Derivative-45 | 7.149 | 1.43% | 1.864 | 4.19% | 1.535 | 34.65% |
Derivative-46 | 7.155 | 1.52% | 1.953 | 9.17% | 1.614 | 41.58% |
Derivative-47 | 6.953 | −1.35% | 1.767 | −1.23% | 1.919 | 68.33% |
Derivative-48 | 7.152 | 1.48% | 1.921 | 7.38% | 1.669 | 46.40% |
Evaluation Project | PAZ | Derivative-1 | Derivative-2 | Derivative-3 |
---|---|---|---|---|
Comprehensive evaluation index | 0.925 | 0.619 | 0.578 | 0.649 |
−33.08% | −37.51% | −29.84% | ||
Convulsive Toxicity | 74.075 | 62.218 | 60.048 | 63.499 |
−16.01% | −18.94% | −14.28% | ||
CEI × 50% | - | −16.54% | −18.76% | −14.92% |
Relative error | 3.23% | 0.96% | 4.30% | |
Gastrointestinal Toxicity | 99.890 | 87.029 | 85.286 | 88.230 |
−12.88% | −14.62% | −11.67% | ||
CEI × 40% | - | −13.23% | −15.01% | −11.94% |
Relative error | 2.70% | 2.57% | 2.20% | |
Cardiotoxicity | 93.715 | 91.282 | 91.352 | 91.266 |
−2.60% | −2.52% | −2.61% | ||
CEI × 10% | - | −3.31% | −3.75% | −2.98% |
Relative error | 15.07% | 32.78% | 12.42% |
Compounds | Frequency/(cm−1) | ΔG/(a.u.) | ΔE/(a.u.) |
---|---|---|---|
Path 1 (–CH3) | 35.02 | −0.026 | 39.307 |
Path 2 (–H) | 39.97 | −0.023 | 39.439 |
Path 3 (–C2H5) | 35.60 | −0.023 | 40.617 |
Molecule | Medium | Carcinogenicity | Fish | Water Fleas | Shrimp | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|
ADD | HI | RI | ADD | HI | RI | ADD | HI | RI | |||
Derivative-1 | sensitive | Carcinogenic | 0.0002 | 0.0117 | 2.81 × 10−5 | 0.0001 | 0.0055 | 1.32 × 10−5 | 4.36 × 10−5 | 0.0022 | 5.23 × 10−6 |
Non-Carcinogenic | 8.03 × 10−5 | 0.0040 | 9.64 × 10−6 | 3.77 × 10−5 | 0.0019 | 4.53 × 10−6 | 1.49 × 10−5 | 0.0007 | 1.79 × 10−6 | ||
Non-sensitive | Carcinogenic | 9.41 × 10−5 | 0.0047 | 1.13 × 10−5 | 4.42 × 10−5 | 0.0022 | 5.30 × 10−6 | 1.75 × 10−5 | 0.0009 | 2.10 × 10−6 | |
Non-Carcinogenic | 3.36 × 10−5 | 0.0017 | 4.03 × 10−6 | 1.58 × 10−5 | 0.0008 | 1.89 × 10−6 | 6.25 × 10−6 | 0.0003 | 7.50 × 10−7 | ||
Derivative-2 | sensitive | Carcinogenic | 0.0005 | 0.0248 | 5.94 × 10−5 | 0.0003 | 0.0134 | 3.21 × 10−5 | 0.0001 | 0.0067 | 1.60 × 10−5 |
Non-Carcinogenic | 0.0002 | 0.0085 | 2.04 × 10−5 | 9.19 × 10−5 | 0.0046 | 1.10 × 10−5 | 4.58 × 10−5 | 0.0023 | 5.50 × 10−6 | ||
Non-sensitive | Carcinogenic | 0.0002 | 0.0100 | 2.39 × 10−5 | 0.0001 | 0.0054 | 1.29 × 10−5 | 5.37 × 10−5 | 0.0027 | 6.44 × 10−6 | |
Non-Carcinogenic | 7.11 × 10−5 | 0.0036 | 8.53 × 10−6 | 3.85 × 10−5 | 0.0019 | 4.61 × 10−6 | 1.92 × 10−5 | 0.0010 | 2.30 × 10−6 | ||
Derivative-3 | sensitive | Carcinogenic | 0.0001 | 0.0052 | 1.21 × 10−5 | 4.17 × 10−5 | 0.0021 | 5.00 × 10−6 | 1.29 × 10−5 | 0.0006 | 1.55 × 10−6 |
Non-Carcinogenic | 3.55 × 10−5 | 0.0018 | 4.26 × 10−6 | 1.43 × 10−5 | 0.0007 | 1.72 × 10−6 | 4.41 × 10−6 | 0.0002 | 5.30 × 10−7 | ||
Non-sensitive | Carcinogenic | 4.16 × 10−5 | 0.0021 | 4.99 × 10−6 | 1.68 × 10−5 | 0.0008 | 2.01 × 10−6 | 5.17 × 10−6 | 0.0003 | 6.21 × 10−7 | |
Non-Carcinogenic | 1.48 × 10−5 | 0.0007 | 1.78 × 10−6 | 5.98 × 10−6 | 0.0003 | 7.18 × 10−7 | 1.85 × 10−6 | 9.24 × 10−5 | 2.22 × 10−7 |
Compounds | Pred.59 | Relative Error | Pred.61 | Relative Error | Pred. AVG * | Relative Error |
---|---|---|---|---|---|---|
PAZ | 7.048 | |||||
PAZ-Cl-1 | 7.448 | 5.68% | 7.992 | 13.39% | 7.720 | 9.53% |
PAZ-Cl-2 | 7.719 | 9.52% | 8.113 | 15.11% | 7.916 | 12.32% |
PAZ-Cl-3 | 7.806 | 10.75% | 7.991 | 13.38% | 7.899 | 12.07% |
PAZ-Cl-4 | 7.588 | 7.66% | 8.195 | 16.27% | 7.891 | 11.96% |
PAZ-Cl-5 | 7.378 | 4.68% | 7.755 | 10.03% | 7.567 | 7.36% |
PAZ-Cl-6 | 7.275 | 3.22% | 7.678 | 8.94% | 7.477 | 6.09% |
PAZ-Cl-7 | 7.149 | 1.43% | 7.533 | 6.88% | 7.341 | 4.16% |
PAZ-Cl-8 | 6.967 | −1.15% | 7.235 | 2.65% | 7.101 | 0.75% |
PAZ-Cl-9 | 6.829 | −3.11% | 7.355 | 4.36% | 7.092 | 0.62% |
PAZ-Cl-10 | 7.497 | 6.37% | 7.709 | 9.38% | 7.603 | 7.87% |
PAZ-Cl-11 | 7.481 | 6.14% | 7.670 | 8.83% | 7.575 | 7.48% |
PAZ-Cl-12 | 7.415 | 5.21% | 7.649 | 8.53% | 7.532 | 6.87% |
PAZ-Cl-13 | 7.375 | 4.64% | 7.572 | 7.43% | 7.473 | 6.03% |
Compounds | Pred.59 | Relative Error | Pred.61 | Relative Error | Pred. AVG * | Relative Error |
---|---|---|---|---|---|---|
Derivative-1 | 7.404 | |||||
Derivative-1-Cl-1 | 7.335 | −0.93% | 7.907 | 6.79% | 7.621 | 2.93% |
Derivative-1-Cl-2 | 7.439 | 0.47% | 7.745 | 4.61% | 7.592 | 2.54% |
Derivative-1-Cl-3 | 7.523 | 1.61% | 7.615 | 2.85% | 7.569 | 2.23% |
Derivative-1-Cl-4 | 7.162 | −3.27% | 7.466 | 0.84% | 7.314 | −1.22% |
Derivative-1-Cl-5 | 6.506 | −12.13% | 6.524 | −11.89% | 6.515 | −12.01% |
Derivative-1-Cl-6 | 6.815 | −7.96% | 7.227 | −2.39% | 7.021 | −5.17% |
Derivative-1-Cl-7 | 6.823 | −7.85% | 7.200 | −2.76% | 7.011 | −5.31% |
Derivative-1-Cl-8 | 7.125 | −3.77% | 7.181 | −3.01% | 7.153 | −3.39% |
Derivative-1-Cl-9 | 7.076 | −4.43% | 7.119 | −3.85% | 7.097 | −4.15% |
Derivative-1-Cl-10 | 7.012 | −5.29% | 7.100 | −4.11% | 7.056 | −4.70% |
Derivative-1-Cl-11 | 7.027 | −5.09% | 7.024 | −5.13% | 7.025 | −5.12% |
Derivative-2 | 7.575 | |||||
Derivative-2-Cl-1 | 7.049 | −6.94% | 7.399 | −2.32% | 7.224 | −4.63% |
Derivative-2-Cl-2 | 7.145 | −5.68% | 7.293 | −3.72% | 7.219 | −4.70% |
Derivative-2-Cl-3 | 7.246 | −4.34% | 7.167 | −5.39% | 7.207 | −4.86% |
Derivative-2-Cl-4 | 6.506 | −14.11% | 6.524 | −13.87% | 6.515 | −13.99% |
Derivative-2-Cl-5 | 6.815 | −10.03% | 7.227 | −4.59% | 7.021 | −7.31% |
Derivative-2-Cl-6 | 6.823 | −9.93% | 7.200 | −4.95% | 7.011 | −7.45% |
Derivative-2-Cl-7 | 7.125 | −5.94% | 7.181 | −5.20% | 7.153 | −5.57% |
Derivative-2-Cl-8 | 7.076 | −6.59% | 7.119 | −6.02% | 7.097 | −6.31% |
Derivative-2-Cl-9 | 7.012 | −7.43% | 7.100 | −6.27% | 7.056 | −6.85% |
Derivative-2-Cl-10 | 7.027 | −7.23% | 7.024 | −7.27% | 7.025 | −7.26% |
Derivative-3 | 7.322 | |||||
Derivative-3-Cl-1 | 7.396 | 1.01% | 7.951 | 8.59% | 7.674 | 4.81% |
Derivative-3-Cl-2 | 7.493 | 2.34% | 7.811 | 6.68% | 7.652 | 4.51% |
Derivative-3-Cl-3 | 7.578 | 3.50% | 7.683 | 4.93% | 7.630 | 4.21% |
Derivative-3-Cl-4 | 7.162 | −2.19% | 7.466 | 1.97% | 7.314 | −0.11% |
Derivative-3-Cl-5 | 6.506 | −11.14% | 6.524 | −10.90% | 6.515 | −11.02% |
Derivative-3-Cl-6 | 6.815 | −6.92% | 7.227 | −1.30% | 7.021 | −4.11% |
Derivative-3-Cl-7 | 6.823 | −6.82% | 7.200 | −1.67% | 7.011 | −4.25% |
Derivative-3-Cl-8 | 7.125 | −2.69% | 7.181 | −1.93% | 7.153 | −2.31% |
Derivative-3-Cl-9 | 7.076 | −3.36% | 7.119 | −2.77% | 7.097 | −3.07% |
Derivative-3-Cl-10 | 7.012 | −4.23% | 7.100 | −3.03% | 7.056 | −3.63% |
Derivative-3-Cl-11 | 7.027 | −4.03% | 7.024 | −4.07% | 7.025 | −4.06% |
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
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Ren, Z.; Wang, Y.; Xu, H.; Li, Y.; Han, S. Fuzzy Comprehensive Evaluation Assistant 3D-QSAR of Environmentally Friendly FQs to Reduce ADRs. Int. J. Environ. Res. Public Health 2019, 16, 3161. https://doi.org/10.3390/ijerph16173161
Ren Z, Wang Y, Xu H, Li Y, Han S. Fuzzy Comprehensive Evaluation Assistant 3D-QSAR of Environmentally Friendly FQs to Reduce ADRs. International Journal of Environmental Research and Public Health. 2019; 16(17):3161. https://doi.org/10.3390/ijerph16173161
Chicago/Turabian StyleRen, Zhixing, Yingwei Wang, Haihong Xu, Yufei Li, and Song Han. 2019. "Fuzzy Comprehensive Evaluation Assistant 3D-QSAR of Environmentally Friendly FQs to Reduce ADRs" International Journal of Environmental Research and Public Health 16, no. 17: 3161. https://doi.org/10.3390/ijerph16173161