Integration of Fuzzy Matter-Element Method and 3D-QSAR Model for Generation of Environmentally Friendly Quinolone Derivatives
Abstract
:1. Introduction
2. Materials and Methods
2.1. Data Sources
2.2. Calculation of the CI Based on Fuzzy Matter-Element Method
2.2.1. Construction of Composite Fuzzy Matter-Element Matrix about QAs’ CI
2.2.2. Determination of Subordination Membership Degree of QAs’ CI
2.2.3. Determination of Standard Fuzzy Matter-Element and Variance Compound Fuzzy Matter-Element Matrix for the CI of QAs’ IRI and UVI
2.2.4. Determination of Weighting for Evaluation Index of the CI of QAs’ IRI and UVI
2.2.5. Euclidean Closeness Calculation for the CI of QAs’ IRI and UVI
2.3. Construction of 3D-QSAR Model to Generate Environmentally Friendly QAs
3. Results and Discussion
3.1. Calculation of QAs’ IRI and UVI based on DFT
3.2. Determination of CI of QAs’ IRI and UVI Based on Fuzzy Matter-Element Method
3.2.1. Subordination Membership Degree, Standard Fuzzy Matter-Element and Variance Compound Fuzzy Matter-Element Matrix
3.2.2. Comprehensive Weightings for CI of QAs’ IRI and UVI
3.2.3. CI of QAs’ IRI and UVI
3.3. Construction and Evaluation of 3D-QSAR Model Based on CI of QAs’ IRI and UVI
3.3.1. Construction of the 3D-QSAR Model
3.3.2. Performance Evaluation of the 3D-QSAR Model
3.4. Determination of Substitution Characteristics Based on the Contour Maps
3.5. Evaluation of Molecular Spectral Characteristics, Functional Characteristics, Environmental Friendliness, and Stability of the QA Derivatives
3.5.1. Molecular Spectral Characteristics
3.5.2. The Enhancement of CI, IRI, and UVI of QA Derivatives’
The Quantitative Mechanism Analysis of the Spectral Enhancement of QA Derivatives Based on the Contour Map
The Quantitative Mechanism Analysis of the Spectral Enhancement of QA Derivatives Based on the Modified Positions and the Properties of Substituted Groups
3.5.3. Molecular Stability Evaluation of QA Derivatives
3.5.4. Functional and Environmental Friendliness Evaluation of QA derivatives
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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No. | Name | IRI | UVI |
---|---|---|---|
Compound 1 | Difloxacin | 1924.76 | 2829.18 |
Compound 2 | Enrofloxacin | 1289.58 | 4394.34 |
Compound 3 | Norfloxacin | 1180.48 | 4627.19 |
Compound 4 | Lomefloxacin | 1788.98 | 1950.61 |
Compound 5 | Ofloxacin | 1428.91 | 3692.38 |
Compound 6 | Pefloxacin | 1587.11 | 3542.25 |
Compound 7 | Fleroxacin | 1882.42 | 1842.68 |
Compound 8 | Ciprofloxacin | 1247.65 | 4045.59 |
Compound 9 | Balofloxacin | 1368.19 | 3220.34 |
Compound 10 | Marbofloxacin | 1265.41 | 264.82 |
Compound 11 | Pipemidic acid | 2430.36 | 2563.72 |
Compound 12 | Cinoxacin | 1631.51 | 9680.14 |
Compound 13 | Enoxacin | 3427.59 | 8254.09 |
Compound 14 | Gatifloxacin | 1363.79 | 2835.67 |
Compound 15 | Levofloxacin | 1943.37 | 575.6 |
Compound 16 | Rufloxacin | 1015.14 | 437.85 |
Compound 17 | Pazufloxacin | 800.37 | 4259.61 |
Compound 18 | Nadifloxacin | 1623.96 | 2878.37 |
Compound 19 | Sparfloxacin | 1185.52 | 2542.11 |
Compound 20 | Sarafloxacin | 1539.67 | 2605.82 |
Compound 21 | Besifloxacin | 1682.72 | 3943.26 |
Compound 22 | Clinafloxacin | 1571.06 | 4875.36 |
Compound 23 | Grepafloxacin | 1489.4 | 2390.87 |
Compound 24 | Temafloxacin | 2155.95 | 8643.35 |
Mi | R’mn | RΔ | Normalization | |||
---|---|---|---|---|---|---|
C1 | C2 | C1 | C2 | C1 | C2 | |
M1 | 0.5615 | 0.2923 | 0.1922 | 0.5009 | 0.4280 | 0.2724 |
M2 | 0.3762 | 0.4540 | 0.3891 | 0.2982 | 0.1862 | 0.4386 |
M3 | 0.3444 | 0.4780 | 0.4298 | 0.2725 | 0.1447 | 0.4633 |
M4 | 0.5219 | 0.2015 | 0.2285 | 0.6376 | 0.3763 | 0.1790 |
M5 | 0.4169 | 0.3814 | 0.3400 | 0.3826 | 0.2392 | 0.3640 |
M6 | 0.4630 | 0.3659 | 0.2883 | 0.4020 | 0.2995 | 0.3481 |
M7 | 0.5492 | 0.1904 | 0.2032 | 0.6555 | 0.4119 | 0.1676 |
M8 | 0.3640 | 0.4179 | 0.4045 | 0.3388 | 0.1702 | 0.4016 |
M9 | 0.3992 | 0.3327 | 0.3610 | 0.4453 | 0.2161 | 0.3139 |
M10 | 0.3692 | 0.0274 | 0.3979 | 0.9460 | 0.1770 | 0.0000 |
M11 | 0.7091 | 0.2648 | 0.0846 | 0.5405 | 0.6204 | 0.2442 |
M12 | 0.4760 | 1.0000 | 0.2746 | 0.0000 | 0.3164 | 1.0000 |
M13 | 1.0000 | 0.8527 | 0.0000 | 0.0217 | 1.0000 | 0.8485 |
M14 | 0.3979 | 0.2929 | 0.3625 | 0.4999 | 0.2145 | 0.2730 |
M15 | 0.5670 | 0.0595 | 0.1875 | 0.8846 | 0.4351 | 0.0330 |
M16 | 0.2962 | 0.0452 | 0.4954 | 0.9116 | 0.0817 | 0.0184 |
M17 | 0.2335 | 0.4400 | 0.5875 | 0.3136 | 0.0000 | 0.4243 |
M18 | 0.4738 | 0.2973 | 0.2769 | 0.4937 | 0.3135 | 0.2776 |
M19 | 0.3459 | 0.2626 | 0.4279 | 0.5437 | 0.1466 | 0.2419 |
M20 | 0.4492 | 0.2692 | 0.3034 | 0.5341 | 0.2814 | 0.2486 |
M21 | 0.4909 | 0.4074 | 0.2591 | 0.3512 | 0.3358 | 0.3907 |
M22 | 0.4584 | 0.5036 | 0.2934 | 0.2464 | 0.2933 | 0.4897 |
M23 | 0.4345 | 0.2470 | 0.3198 | 0.5670 | 0.2623 | 0.2258 |
M24 | 0.6290 | 0.8929 | 0.1376 | 0.0115 | 0.5160 | 0.8899 |
Entropy | Entropy Weights | Comprehensive Weights | |||
---|---|---|---|---|---|
S1 | S2 | W1 | W2 | W’1 | W’2 |
−0.9966 | −0.9950 | 0.5002 | 0.4998 | 0.5001 | 0.4999 |
ei | Comprehensive Effects | ei | Comprehensive Effects | ei | Comprehensive Effects |
---|---|---|---|---|---|
e1 | 0.4113 | e9 | 0.3651 | e17 | 0.3288 |
e2 | 0.4138 | e10 | 0.1803 | e18 | 0.3793 |
e3 | 0.4074 | e11 | 0.4409 | e19 | 0.3030 |
e4 | 0.3419 | e12 | 0.6295 | e20 | 0.3529 |
e5 | 0.3989 | e13 | 0.8958 | e21 | 0.4476 |
e6 | 0.4125 | e14 | 0.3433 | e22 | 0.4805 |
e7 | 0.3447 | e15 | 0.2678 | e23 | 0.3341 |
e8 | 0.3904 | e16 | 0.1613 | e24 | 0.7269 |
No. | Calculated Value | Predicted Value | Relative Deviation |
---|---|---|---|
a Compound 3 | 0.4074 | 0.3990 | 2.06% |
a Compound 4 | 0.3419 | 0.3540 | −3.54% |
b Compound 7 | 0.3447 | 0.3970 | −15.17% |
a Compound 8 | 0.3904 | 0.4170 | −6.81% |
a Compound 9 | 0.3651 | 0.3620 | 0.85% |
a Compound 10 | 0.1803 | 0.1630 | 9.60% |
a Compound 11 | 0.4409 | 0.4430 | −0.48% |
a Compound 12 | 0.6295 | 0.6520 | −3.57% |
a Compound 15 | 0.2678 | 0.2680 | −0.07% |
a Compound 16 | 0.1613 | 0.1950 | −20.89% |
b Compound 18 | 0.3793 | 0.3800 | −0.18% |
b Compound 20 | 0.3529 | 0.3770 | −6.83% |
a Compound 21 | 0.4476 | 0.4300 | 3.93% |
a Compound 22 | 0.4805 | 0.4390 | 8.64% |
a Compound 23 | 0.3341 | 0.3290 | 1.53% |
a,b Compound 24 | 0.7269 | 0.7240 | 0.40% |
QA Derivatives | Position of Substitution | CI | Relative Deviation | IRI | Relative Deviation | UVI | Relative Deviation | |
---|---|---|---|---|---|---|---|---|
1-Position | 2-Position | |||||||
Marbofloxacin | CH3 | CH3 | 0.1803 | 1265.4100 | 264.8200 | |||
Derivative 1 | SiH3 | - | 0.2820 | 56.41% | 2046.4446 | 61.72% | 920.4496 | 247.58% |
Derivative 2 | C2H5 | - | 0.2690 | 49.20% | 2128.1390 | 68.18% | 749.8942 | 183.17% |
Derivative 3 | PH2 | - | 0.2850 | 58.07% | 2051.1622 | 62.09% | 916.2205 | 245.98% |
Derivative 4 | C3H7 | - | 0.2690 | 49.20% | 2113.4890 | 67.02% | 711.2135 | 168.56% |
Derivative 5 | C4H9 | - | 0.2690 | 49.20% | 2133.0449 | 68.57% | 714.4963 | 169.80% |
Derivative 6 | C5H11 | - | 0.2690 | 49.20% | 2133.0449 | 68.57% | 712.8530 | 169.18% |
Derivative 7 | - | CH2F | 0.3510 | 94.68% | 2051.1622 | 62.09% | 1492.7944 | 463.70% |
Derivative 8 | - | C2H3 | 0.3210 | 78.04% | 2023.0192 | 59.87% | 1205.0359 | 355.04% |
Derivative 9 | - | C2H | 0.3100 | 71.94% | 1976.9696 | 56.23% | 805.3784 | 204.12% |
Derivative 10 | - | CH2OH | 0.2930 | 62.51% | 2013.7242 | 59.14% | 972.7472 | 267.32% |
Derivative 11 | - | NH2 | 0.3030 | 68.05% | 2051.1622 | 62.09% | 629.5062 | 137.71% |
Derivative 12 | - | NO | 0.3530 | 95.78% | 2009.0928 | 58.77% | 1061.6956 | 300.91% |
Derivative 13 | - | NO2 | 0.3590 | 99.11% | 1995.2623 | 57.68% | 1142.8783 | 331.57% |
Derivative 14 | SiH3 | CH2F | 0.3550 | 96.89% | 2060.6299 | 62.84% | 1442.1154 | 444.56% |
Derivative 15 | PH2 | CH2F | 0.3510 | 94.68% | 2046.4446 | 61.72% | 1492.7944 | 463.70% |
Derivative 16 | C3H7 | CH2F | 0.8050 | 346.48% | 2511.8864 | 98.50% | 8729.7137 | 3196.47% |
Derivative 17 | C4H9 | CH2F | 0.8060 | 347.03% | 2511.8864 | 98.50% | 8729.7137 | 3196.47% |
Derivative 18 | C5H11 | CH2F | 0.8060 | 347.03% | 2511.8864 | 98.50% | 8729.7137 | 3196.47% |
Derivative 19 | H | C2H3 | 0.8150 | 352.02% | 2624.2185 | 107.38% | 9571.9407 | 3514.51% |
Derivative 20 | SiH3 | C2H3 | 0.8210 | 355.35% | 2630.2680 | 107.86% | 9354.0567 | 3432.23% |
Derivative 21 | C2H5 | C2H3 | 0.8190 | 354.24% | 2630.2680 | 107.86% | 9332.5430 | 3424.11% |
Derivative 22 | PH2 | C2H3 | 0.8180 | 353.69% | 2630.2680 | 107.86% | 9506.0479 | 3489.63% |
Derivative 23 | C3H7 | C2H3 | 0.8210 | 355.35% | 2636.3314 | 108.34% | 8356.0302 | 3055.36% |
Derivative 24 | C4H9 | C2H3 | 0.8210 | 355.35% | 2636.3314 | 108.34% | 8298.5077 | 3033.64% |
Derivative 25 | C5H11 | C2H3 | 0.8210 | 355.35% | 2654.6056 | 109.78% | 7870.4579 | 2872.00% |
Derivative 26 | H | C2H | 0.8160 | 352.58% | 2570.3958 | 103.13% | 9549.9259 | 3506.20% |
Derivative 27 | SiH3 | C2H | 0.8210 | 355.35% | 2594.1794 | 105.01% | 9141.1324 | 3351.83% |
Derivative 28 | C2H5 | C2H | 0.8210 | 355.35% | 2612.1614 | 106.43% | 8974.2879 | 3288.83% |
Derivative 29 | PH2 | C2H | 0.8170 | 353.13% | 2588.2129 | 104.54% | 9484.1846 | 3481.37% |
Derivative 30 | C3H7 | C2H | 0.7960 | 341.49% | 2588.2129 | 104.54% | 6180.1640 | 2233.72% |
Derivative 31 | C4H9 | C2H | 0.7960 | 341.49% | 2588.2129 | 104.54% | 5807.6442 | 2093.05% |
Derivative 32 | C5H11 | C2H | 0.7950 | 340.93% | 2588.2129 | 104.54% | 5754.3994 | 2072.95% |
Derivative 33 | H | CH2OH | 0.8200 | 354.80% | 2523.4808 | 99.42% | 9660.5088 | 3547.95% |
Derivative 34 | SiH3 | CH2OH | 0.8260 | 358.13% | 2535.1286 | 100.34% | 9397.2331 | 3448.54% |
Derivative 35 | C2H5 | CH2OH | 0.8250 | 357.57% | 2535.1286 | 100.34% | 8749.8378 | 3204.07% |
Derivative 36 | PH2 | CH2OH | 0.8220 | 355.91% | 2529.2980 | 99.88% | 9616.1228 | 3531.19% |
Derivative 37 | C3H7 | CH2OH | 0.8230 | 356.46% | 2523.4808 | 99.42% | 8933.0548 | 3273.26% |
Derivative 38 | C4H9 | CH2OH | 0.8230 | 356.46% | 2529.2980 | 99.88% | 8974.2879 | 3288.83% |
Derivative 39 | C5H11 | CH2OH | 0.8230 | 356.46% | 2529.2980 | 99.88% | 8974.2879 | 3288.83% |
Derivative 40 | H | NH2 | 0.7920 | 339.27% | 2546.8303 | 101.27% | 8609.9375 | 3151.24% |
Derivative 41 | SiH3 | NH2 | 0.8000 | 343.70% | 2558.5859 | 102.19% | 8317.6377 | 3040.86% |
Derivative 42 | C2H5 | NH2 | 0.8020 | 344.81% | 2582.2602 | 104.07% | 8336.8118 | 3048.11% |
Derivative 43 | PH2 | NH2 | 0.8010 | 344.26% | 2582.2602 | 104.07% | 8336.8118 | 3048.11% |
Derivative 44 | C3H7 | NH2 | 0.7720 | 328.18% | 2594.1794 | 105.01% | 6123.5039 | 2212.33% |
Derivative 45 | C4H9 | NH2 | 0.3450 | 91.35% | 2162.7185 | 70.91% | 2805.4336 | 959.37% |
Derivative 46 | C5H11 | NH2 | 0.3730 | 106.88% | 2187.7616 | 72.89% | 2792.5438 | 954.51% |
Derivative 47 | H | NO | 0.3200 | 77.48% | 2137.9621 | 68.95% | 1606.9413 | 506.81% |
Derivative 48 | SiH3 | NO | 0.2730 | 51.41% | 2192.8049 | 73.29% | 1166.8096 | 340.60% |
Derivative 49 | C2H5 | NO | 0.2420 | 34.22% | 2157.7444 | 70.52% | 984.0111 | 271.58% |
Derivative 50 | PH2 | NO | 0.4150 | 130.17% | 1972.4227 | 55.87% | 2074.9135 | 683.52% |
Derivative 51 | C3H7 | NO | 0.2440 | 35.33% | 2128.1390 | 68.18% | 990.8319 | 274.15% |
Derivative 52 | C4H9 | NO | 0.2460 | 36.44% | 2137.9621 | 68.95% | 933.2543 | 252.41% |
Derivative 53 | C5H11 | NO | 0.2460 | 36.44% | 2128.1390 | 68.18% | 937.5620 | 254.04% |
Derivative 54 | H | NO2 | 0.3170 | 75.82% | 2079.6967 | 64.35% | 1534.6170 | 479.49% |
Derivative 55 | SiH3 | NO2 | 0.2530 | 40.32% | 2113.4890 | 67.02% | 1156.1122 | 336.57% |
Derivative 56 | C2H5 | NO2 | 0.2340 | 29.78% | 2094.1125 | 65.49% | 1324.3415 | 400.09% |
Derivative 57 | C3H7 | NO2 | 0.2350 | 30.34% | 2074.9135 | 63.97% | 918.3326 | 246.78% |
Derivative 58 | C4H9 | NO2 | 0.2360 | 30.89% | 2089.2961 | 65.11% | 889.2011 | 235.78% |
Derivative 59 | C5H11 | NO2 | 0.2360 | 30.89% | 2089.2961 | 65.11% | 870.9636 | 228.89% |
Derivative 60 | H | CHO | 0.4500 | 149.58% | 1981.5270 | 56.59% | 3019.9517 | 1040.38% |
Derivative 61 | SiH3 | CHO | 0.4110 | 127.95% | 1896.7059 | 49.89% | 2488.8573 | 839.83% |
Derivative 62 | C2H5 | CHO | 0.3270 | 81.36% | 1909.8533 | 50.93% | 1753.8805 | 562.29% |
Derivative 63 | C3H7 | CHO | 0.3130 | 73.60% | 1918.6687 | 51.62% | 1774.1895 | 569.96% |
Derivative 64 | C4H9 | CHO | 0.3260 | 80.81% | 1927.5249 | 52.32% | 2032.3570 | 667.45% |
Derivative 65 | C5H11 | CHO | 0.3270 | 81.36% | 1923.0917 | 51.97% | 2018.3664 | 662.17% |
Derivative 66 | H | COOH | 0.4550 | 152.36% | 2065.3802 | 63.22% | 2951.2092 | 1014.42% |
Derivative 67 | SiH3 | COOH | 0.3960 | 119.63% | 2074.9135 | 63.97% | 2301.4418 | 769.06% |
Derivative 68 | C2H5 | COOH | 0.3170 | 75.82% | 1995.2623 | 57.68% | 1923.0917 | 626.19% |
Derivative 69 | C3H7 | COOH | 0.3030 | 68.05% | 1986.0949 | 56.95% | 1905.4607 | 619.53% |
Derivative 70 | C4H9 | COOH | 0.3130 | 73.60% | 1986.0949 | 56.95% | 2108.6281 | 696.25% |
Levofloxacin | CH3 | CH3 | 0.2678 | 1943.3700 | 575.6000 | |||
Derivative 71 | C4H9 | 0.7850 | 193.13% | 2409.9054 | 24.01% | 7430.1914 | 1190.86% | |
Derivative 72 | C4H9 | C2H3 | 0.7500 | 180.06% | 2636.3314 | 35.66% | 5834.4510 | 913.63% |
Derivative 73 | C3H7 | OH | 0.7430 | 177.45% | 2552.7013 | 31.35% | 2108.6281 | 266.34% |
Derivative 74 | C3H7 | OH | 0.6690 | 149.81% | 2328.0913 | 19.80% | 1741.8069 | 202.61% |
Derivative 75 | H | OH | 0.7210 | 169.23% | 2404.3628 | 23.72% | 3881.5037 | 574.34% |
Derivative 76 | OCH3 | 0.7670 | 186.41% | 2488.8573 | 28.07% | 7328.2453 | 1173.15% | |
Derivative 77 | C2H5 | OCH3 | 0.7420 | 177.07% | 2624.2185 | 35.03% | 5296.6344 | 820.19% |
Derivative 78 | SiH3 | OCH3 | 0.7560 | 182.30% | 2529.2980 | 30.15% | 7533.5556 | 1208.82% |
Derivative 79 | C5H11 | OCH3 | 0.7560 | 182.30% | 2477.4221 | 27.48% | 1496.2357 | 159.94% |
Derivative 80 | C3H7 | CN | 0.7550 | 181.93% | 2618.1830 | 34.72% | 6095.3690 | 958.96% |
Derivative 81 | SiH3 | NO | 0.7560 | 182.30% | 2275.0974 | 17.07% | 3169.5675 | 450.65% |
Derivative 82 | NO2 | 0.7530 | 181.18% | 2642.4088 | 35.97% | 5035.0061 | 774.74% | |
Derivative 83 | C2H5 | NO2 | 0.7590 | 183.42% | 2466.0393 | 26.89% | 5223.9619 | 807.57% |
Derivative 84 | SiH3 | NO2 | 0.7680 | 186.78% | 2387.8113 | 22.87% | 7177.9429 | 1147.04% |
Derivative 85 | C3H7 | NO2 | 0.7530 | 181.18% | 2506.1093 | 28.96% | 5105.0500 | 786.91% |
Derivative 86 | C4H9 | NO2 | 0.7540 | 181.55% | 2588.2129 | 33.18% | 5495.4087 | 854.73% |
Derivative 87 | CHO | 0.7850 | 193.13% | 2488.8573 | 28.07% | 1741.8069 | 202.61% |
Molecular Substitution Type | QA Derivatives | Modified Positions and Properties of Substituted Groups | |||||||
---|---|---|---|---|---|---|---|---|---|
1-Position Positive | Relative Deviation | 2-Position Negative | Relative Deviation | 2-Position Bigger Group | Relative Deviation | 2-Position Coupling | 1, 2-Position Coupling | ||
Marbofloxacin/Levofloxacin | 2.331 | - | 2.331 | - | 15 | - | - | - | |
Monosubstitution | Derivative 1 | 2.120 | 9.05% | - | - | - | - | - | - |
Derivative 2 | 2.315 | 0.69% | - | - | - | - | - | - | |
Derivative 3 | 2.154 | 7.59% | - | - | - | - | - | - | |
Derivative 4 | 2.314 | 0.73% | - | - | - | - | - | - | |
Derivative 5 | 2.313 | 0.77% | - | - | - | - | - | - | |
Derivative 6 | 2.312 | 0.82% | - | - | - | - | - | - | |
Derivative 71 | 2.313 | 0.77% | - | - | - | - | - | - | |
Derivative 7 | - | - | 2.644 | 13.43% | 33 | 120.00% | 66.71% | - | |
Derivative 8 | - | - | 2.358 | 1.16% | 27 | 80.00% | 40.58% | - | |
Derivative 9 | - | - | 2.530 | 8.54% | 25 | 66.67% | 37.60% | - | |
Derivative 10 | - | - | 2.491 | 6.86% | 31 | 106.67% | 56.77% | - | |
Derivative 11 | - | - | 2.437 | 4.55% | 16 | 6.67% | 5.61% | - | |
Derivative 12 | - | - | 2.920 | 25.27% | 30 | 100.00% | 62.63% | - | |
Derivative 13 | - | - | 3.104 | 33.16% | 46 | 206.67% | 119.91% | - | |
Derivative 76 | - | - | 2.460 | 5.53% | 31 | 106.67% | 56.10% | - | |
Derivative 82 | - | - | 3.104 | 33.16% | 46 | 206.67% | 119.91% | - | |
Derivative 87 | - | - | 2.647 | 13.56% | 29 | 93.33% | 53.44% | - | |
Disubstituted | Derivative 14 | 2.120 | 9.05% | 2.644 | 13.43% | 33 | 120.00% | 85.90% | 94.95% |
Derivative 15 | 2.154 | 7.59% | 2.644 | 13.43% | 33 | 120.00% | 85.90% | 93.49% | |
Derivative 16 | 2.314 | 0.73% | 2.644 | 13.43% | 33 | 120.00% | 85.90% | 86.63% | |
Derivative 17 | 2.313 | 0.77% | 2.644 | 13.43% | 33 | 120.00% | 85.90% | 86.67% | |
Derivative 18 | 2.312 | 0.82% | 2.644 | 13.43% | 33 | 120.00% | 85.90% | 86.71% | |
Derivative 19 | 2.200 | 5.62% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 60.39% | |
Derivative 20 | 2.120 | 9.05% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 63.82% | |
Derivative 21 | 2.315 | 0.69% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 55.46% | |
Derivative 22 | 2.154 | 7.59% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 62.36% | |
Derivative 23 | 2.314 | 0.73% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 55.50% | |
Derivative 24 | 2.313 | 0.77% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 55.54% | |
Derivative 25 | 2.312 | 0.82% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 55.59% | |
Derivative 26 | 2.200 | 5.62% | 2.530 | 8.54% | 25 | 66.67% | 48.07% | 53.69% | |
Derivative 27 | 2.120 | 9.05% | 2.530 | 8.54% | 25 | 66.67% | 48.07% | 57.12% | |
Derivative 28 | 2.315 | 0.69% | 2.530 | 8.54% | 25 | 66.67% | 48.07% | 48.75% | |
Derivative 29 | 2.154 | 7.59% | 2.530 | 8.54% | 25 | 66.67% | 48.07% | 55.66% | |
Derivative 30 | 2.314 | 0.73% | 2.530 | 8.54% | 25 | 66.67% | 48.07% | 48.79% | |
Derivative 31 | 2.313 | 0.77% | 2.530 | 8.54% | 25 | 66.67% | 48.07% | 48.84% | |
Derivative 32 | 2.312 | 0.82% | 2.530 | 8.54% | 25 | 66.67% | 48.07% | 48.88% | |
Derivative 33 | 2.200 | 5.62% | 2.491 | 6.86% | 31 | 106.67% | 74.73% | 80.35% | |
Derivative 34 | 2.120 | 9.05% | 2.491 | 6.86% | 31 | 106.67% | 74.73% | 83.78% | |
Derivative 35 | 2.315 | 0.69% | 2.491 | 6.86% | 31 | 106.67% | 74.73% | 75.42% | |
Derivative 36 | 2.154 | 7.59% | 2.491 | 6.86% | 31 | 106.67% | 74.73% | 82.32% | |
Derivative 37 | 2.314 | 0.73% | 2.491 | 6.86% | 31 | 106.67% | 74.73% | 75.46% | |
Derivative 38 | 2.313 | 0.77% | 2.491 | 6.86% | 31 | 106.67% | 74.73% | 75.50% | |
Derivative 39 | 2.312 | 0.82% | 2.491 | 6.86% | 31 | 106.67% | 74.73% | 75.54% | |
Derivative 40 | 2.200 | 5.62% | 2.437 | 4.55% | 16 | 6.67% | 5.99% | 11.61% | |
Derivative 41 | 2.120 | 9.05% | 2.437 | 4.55% | 16 | 6.67% | 5.99% | 15.04% | |
Derivative 42 | 2.315 | 0.69% | 2.437 | 4.55% | 16 | 6.67% | 5.99% | 6.67% | |
Derivative 43 | 2.154 | 7.59% | 2.437 | 4.55% | 16 | 6.67% | 5.99% | 13.58% | |
Derivative 44 | 2.314 | 0.73% | 2.437 | 4.55% | 16 | 6.67% | 5.99% | 6.72% | |
Derivative 45 | 2.313 | 0.77% | 2.437 | 4.55% | 16 | 6.67% | 5.99% | 6.76% | |
Derivative 46 | 2.312 | 0.82% | 2.437 | 4.55% | 16 | 6.67% | 5.99% | 6.80% | |
Derivative 47 | 2.200 | 5.62% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 81.71% | |
Derivative 48 | 2.120 | 9.05% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 85.14% | |
Derivative 49 | 2.315 | 0.69% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 76.77% | |
Derivative 50 | 2.154 | 7.59% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 83.68% | |
Derivative 51 | 2.314 | 0.73% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 76.82% | |
Derivative 52 | 2.313 | 0.77% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 76.86% | |
Derivative 53 | 2.312 | 0.82% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 76.90% | |
Derivative 54 | 2.200 | 5.62% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 156.76% | |
Derivative 55 | 2.120 | 9.05% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 160.20% | |
Derivative 56 | 2.315 | 0.69% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 151.83% | |
Derivative 57 | 2.314 | 0.73% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 151.87% | |
Derivative 58 | 2.313 | 0.77% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 151.92% | |
Derivative 59 | 2.312 | 0.82% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 151.96% | |
Derivative 60 | 2.200 | 5.62% | 2.647 | 13.56% | 29 | 93.33% | 67.80% | 73.42% | |
Derivative 61 | 2.120 | 9.05% | 2.647 | 13.56% | 29 | 93.33% | 67.80% | 76.86% | |
Derivative 62 | 2.315 | 0.69% | 2.647 | 13.56% | 29 | 93.33% | 67.80% | 68.49% | |
Derivative 63 | 2.314 | 0.73% | 2.647 | 13.56% | 29 | 93.33% | 67.80% | 68.53% | |
Derivative 64 | 2.313 | 0.77% | 2.647 | 13.56% | 29 | 93.33% | 67.80% | 68.58% | |
Derivative 65 | 2.312 | 0.82% | 2.647 | 13.56% | 29 | 93.33% | 67.80% | 68.62% | |
Derivative 66 | 2.200 | 5.62% | 2.769 | 18.79% | 45 | 200.00% | 142.01% | 147.63% | |
Derivative 67 | 2.120 | 9.05% | 2.769 | 18.79% | 45 | 200.00% | 142.01% | 151.06% | |
Derivative 68 | 2.315 | 0.69% | 2.769 | 18.79% | 45 | 200.00% | 142.01% | 142.70% | |
Derivative 69 | 2.314 | 0.73% | 2.769 | 18.79% | 45 | 200.00% | 142.01% | 142.74% | |
Derivative 70 | 2.313 | 0.77% | 2.769 | 18.79% | 45 | 200.00% | 142.01% | 142.79% | |
Derivative 72 | 2.313 | 0.77% | 2.358 | 1.16% | 27 | 80.00% | 54.77% | 55.54% | |
Derivative 73 | 2.314 | 0.73% | 2.585 | 10.90% | 17 | 13.33% | 12.55% | 13.28% | |
Derivative 74 | 2.314 | 0.73% | 2.585 | 10.90% | 17 | 13.33% | 12.55% | 13.28% | |
Derivative 75 | 2.200 | 5.62% | 2.585 | 10.90% | 17 | 13.33% | 12.55% | 18.17% | |
Derivative 77 | 2.315 | 0.69% | 2.460 | 5.53% | 31 | 106.67% | 74.30% | 74.99% | |
Derivative 78 | 2.120 | 9.05% | 2.460 | 5.53% | 31 | 106.67% | 74.30% | 83.36% | |
Derivative 79 | 2.312 | 0.82% | 2.460 | 5.53% | 31 | 106.67% | 74.30% | 75.12% | |
Derivative 80 | 2.314 | 0.73% | 2.792 | 19.78% | 26 | 73.33% | 56.20% | 56.92% | |
Derivative 81 | 2.120 | 9.05% | 2.920 | 25.27% | 30 | 100.00% | 76.09% | 85.14% | |
Derivative 83 | 2.315 | 0.69% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 151.83% | |
Derivative 84 | 2.120 | 9.05% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 160.20% | |
Derivative 85 | 2.314 | 0.73% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 151.87% | |
Derivative 86 | 2.313 | 0.77% | 3.104 | 33.16% | 46 | 206.67% | 151.15% | 151.92% |
QA Derivatives | Positive Frequency Value | QA Derivatives | Positive Frequency Value | QA Derivatives | Positive Frequency Value |
---|---|---|---|---|---|
Derivative 1 | 20.78 | Derivative 30 | 14.97 | Derivative 59 | 10.15 |
Derivative 2 | 17.07 | Derivative 31 | 14.85 | Derivative 60 | 28.78 |
Derivative 3 | 19.93 | Derivative 32 | 12.63 | Derivative 61 | 18.22 |
Derivative 4 | 15.47 | Derivative 33 | 24.17 | Derivative 62 | 25.68 |
Derivative 5 | 14.17 | Derivative 34 | 17.19 | Derivative 63 | 23.33 |
Derivative 6 | 13.15 | Derivative 35 | 18.39 | Derivative 64 | 21.80 |
Derivative 7 | 25.16 | Derivative 36 | 19.52 | Derivative 65 | 18.79 |
Derivative 8 | 21.84 | Derivative 37 | 19.74 | Derivative 66 | 28.44 |
Derivative 9 | 22.60 | Derivative 38 | 14.32 | Derivative 67 | 23.12 |
Derivative 10 | 20.75 | Derivative 39 | 13.44 | Derivative 68 | 24.75 |
Derivative 11 | 21.58 | Derivative 40 | 31.02 | Derivative 69 | 22.49 |
Derivative 12 | 24.54 | Derivative 41 | 20.39 | Derivative 70 | 20.99 |
Derivative 13 | 22.29 | Derivative 42 | 17.77 | Derivative 71 | 15.37 |
Derivative 14 | 20.67 | Derivative 43 | 20.83 | Derivative 72 | 11.09 |
Derivative 15 | 20.88 | Derivative 44 | 20.82 | Derivative 73 | 15.30 |
Derivative 16 | 18.33 | Derivative 45 | 15.87 | Derivative 74 | 16.74 |
Derivative 17 | 17.08 | Derivative 46 | 12.92 | Derivative 75 | 28.59 |
Derivative 18 | 14.97 | Derivative 47 | 24.63 | Derivative 76 | 21.50 |
Derivative 19 | 21.27 | Derivative 48 | 19.56 | Derivative 77 | 16.28 |
Derivative 20 | 16.15 | Derivative 49 | 21.39 | Derivative 78 | 19.62 |
Derivative 21 | 19.96 | Derivative 50 | 14.89 | Derivative 79 | 9.36 |
Derivative 22 | 18.43 | Derivative 51 | 13.37 | Derivative 80 | 18.66 |
Derivative 23 | 16.27 | Derivative 52 | 12.78 | Derivative 81 | 16.26 |
Derivative 24 | 15.53 | Derivative 53 | 7.10 | Derivative 82 | 21.73 |
Derivative 25 | 14.51 | Derivative 54 | 23.28 | Derivative 83 | 20.00 |
Derivative 26 | 24.80 | Derivative 55 | 20.02 | Derivative 84 | 21.43 |
Derivative 27 | 18.49 | Derivative 56 | 17.86 | Derivative 85 | 18.49 |
Derivative 28 | 21.60 | Derivative 57 | 13.65 | Derivative 86 | 11.53 |
Derivative 29 | 20.14 | Derivative 58 | 12.72 | Derivative 87 | 23.13 |
QA Derivatives | Genotoxicity | Relative Deviation | Bioaccumulation | Relative Deviation | Biodegradability | Relative Deviation |
---|---|---|---|---|---|---|
Marbofloxacin | 8.4600 | 1.1840 | 1.7050 | |||
Derivative 1 | 9.5390 | 12.75% | 0.9650 | −18.50% | 1.7070 | 0.12% |
Derivative 2 | 9.8690 | 16.65% | 1.1630 | −1.77% | 1.7250 | 1.17% |
Derivative 3 | 9.3760 | 10.83% | 0.8900 | −24.83% | 1.7130 | 0.47% |
Derivative 4 | 9.6020 | 13.50% | 1.1730 | −0.93% | 1.7240 | 1.11% |
Derivative 5 | 9.5320 | 12.67% | 1.1740 | −0.84% | 1.7250 | 1.17% |
Derivative 6 | 9.6380 | 13.92% | 1.1750 | −0.76% | 1.7240 | 1.11% |
Derivative 7 | 9.0310 | 6.75% | 1.3610 | 14.95% | 1.7190 | 0.82% |
Derivative 8 | 8.9180 | 5.41% | 1.3730 | 15.96% | 1.7290 | 1.41% |
Derivative 9 | 8.5310 | 0.84% | 1.2810 | 8.19% | 1.7170 | 0.70% |
Derivative 10 | 9.2950 | 9.87% | 1.5920 | 34.46% | 1.7030 | −0.12% |
Derivative 11 | 9.8810 | 16.80% | 1.1110 | −6.17% | 1.7130 | 0.47% |
Derivative 12 | 8.4810 | 0.25% | 1.5260 | 28.89% | 1.6900 | −0.88% |
Derivative 13 | 9.0470 | 6.94% | 1.2460 | 5.24% | 1.7350 | 1.76% |
Derivative 14 | 9.6010 | 13.49% | 1.1590 | −2.11% | 1.7160 | 0.65% |
Derivative 15 | 9.4670 | 11.90% | 1.0520 | −11.15% | 1.7190 | 0.82% |
Derivative 16 | 9.8060 | 15.91% | 0.6090 | −48.56% | 1.4940 | −12.38% |
Derivative 17 | 9.7360 | 15.08% | 0.6080 | −48.65% | 1.4940 | −12.38% |
Derivative 18 | 9.8420 | 16.34% | 0.6060 | −48.82% | 1.4940 | −12.38% |
Derivative 19 | 9.2230 | 9.02% | 0.5660 | −52.20% | 1.5050 | −11.73% |
Derivative 20 | 9.4870 | 12.14% | 0.5650 | −52.28% | 1.4990 | −12.08% |
Derivative 21 | 9.9670 | 17.81% | 0.5720 | −51.69% | 1.5000 | −12.02% |
Derivative 22 | 9.4730 | 11.97% | 0.5430 | −54.14% | 1.5040 | −11.79% |
Derivative 23 | 9.7000 | 14.66% | 0.5760 | −51.35% | 1.5070 | −11.61% |
Derivative 24 | 9.6300 | 13.83% | 0.5760 | −51.35% | 1.5060 | −11.67% |
Derivative 25 | 9.7350 | 15.07% | 0.5760 | −51.35% | 1.5100 | −11.44% |
Derivative 26 | 8.8350 | 4.43% | 0.5470 | −53.80% | 1.5260 | −10.50% |
Derivative 27 | 8.9990 | 6.37% | 0.5450 | −53.97% | 1.5230 | −10.67% |
Derivative 28 | 9.5790 | 13.23% | 0.5550 | −53.13% | 1.5290 | −10.32% |
Derivative 29 | 9.0860 | 7.40% | 0.5230 | −55.83% | 1.5220 | −10.73% |
Derivative 30 | 9.3130 | 10.08% | 0.5910 | −50.08% | 1.5270 | −10.44% |
Derivative 31 | 9.2430 | 9.26% | 0.5950 | −49.75% | 1.5290 | −10.32% |
Derivative 32 | 9.3480 | 10.50% | 0.5970 | −49.58% | 1.5300 | −10.26% |
Derivative 33 | 9.6000 | 13.48% | 0.5350 | −54.81% | 1.5060 | −11.67% |
Derivative 34 | 9.7820 | 15.63% | 0.5330 | −54.98% | 1.5010 | −11.96% |
Derivative 35 | 10.3440 | 22.27% | 0.5450 | −53.97% | 1.5030 | −11.85% |
Derivative 36 | 9.8510 | 16.44% | 0.5120 | −56.76% | 1.5020 | −11.91% |
Derivative 37 | 10.0780 | 19.13% | 0.5440 | −54.05% | 1.4980 | −12.14% |
Derivative 38 | 10.0070 | 18.29% | 0.5440 | −54.05% | 1.4990 | −12.08% |
Derivative 39 | 10.1130 | 19.54% | 0.5440 | −54.05% | 1.5010 | −11.96% |
Derivative 40 | 10.1700 | 20.21% | 0.5020 | −57.60% | 1.5130 | −11.26% |
Derivative 41 | 10.1300 | 19.74% | 0.4950 | −58.19% | 1.5120 | −11.32% |
Derivative 42 | 10.9140 | 29.01% | 0.5150 | −56.50% | 1.5090 | −11.50% |
Derivative 43 | 10.4210 | 23.18% | 0.4680 | −60.47% | 1.5150 | −11.14% |
Derivative 44 | 10.6480 | 25.86% | 0.5600 | −52.70% | 1.5180 | −10.97% |
Derivative 45 | 10.5810 | 25.07% | 1.1810 | −0.25% | 1.7350 | 1.76% |
Derivative 46 | 10.6870 | 26.32% | 1.1840 | 0.00% | 1.7340 | 1.70% |
Derivative 47 | 8.7900 | 3.90% | 1.4680 | 23.99% | 1.7140 | 0.53% |
Derivative 48 | 8.8820 | 4.99% | 1.5270 | 28.97% | 1.7120 | 0.41% |
Derivative 49 | 9.5340 | 12.70% | 1.6600 | 40.20% | 1.7140 | 0.53% |
Derivative 50 | 10.2130 | 20.72% | 1.2030 | 1.60% | 1.7480 | 2.52% |
Derivative 51 | 9.2680 | 9.55% | 1.6710 | 41.13% | 1.7140 | 0.53% |
Derivative 52 | 9.1970 | 8.71% | 1.6780 | 41.72% | 1.7150 | 0.59% |
Derivative 53 | 9.3030 | 9.96% | 1.6730 | 41.30% | 1.7150 | 0.59% |
Derivative 54 | 9.3480 | 10.50% | 1.2920 | 9.12% | 1.7150 | 0.59% |
Derivative 55 | 9.5060 | 12.36% | 1.2600 | 6.42% | 1.7170 | 0.70% |
Derivative 56 | 10.0920 | 19.29% | 1.5080 | 27.36% | 1.7190 | 0.82% |
Derivative 57 | 9.8260 | 16.15% | 1.5030 | 26.94% | 1.7150 | 0.59% |
Derivative 58 | 9.7550 | 15.31% | 1.5080 | 27.36% | 1.7150 | 0.59% |
Derivative 59 | 9.8610 | 16.56% | 1.5100 | 27.53% | 1.7160 | 0.65% |
Derivative 60 | 8.7220 | 3.10% | 0.8730 | −26.27% | 1.6940 | −0.65% |
Derivative 61 | 9.2850 | 9.75% | 0.9190 | −22.38% | 1.6930 | −0.70% |
Derivative 62 | 9.4710 | 11.95% | 1.1430 | −3.46% | 1.7000 | −0.29% |
Derivative 63 | 9.1970 | 8.71% | 1.1680 | −1.35% | 1.7000 | −0.29% |
Derivative 64 | 9.1270 | 7.88% | 1.1810 | −0.25% | 1.7020 | −0.18% |
Derivative 65 | 9.2330 | 9.14% | 1.1870 | 0.25% | 1.7000 | −0.29% |
Derivative 66 | 8.8390 | 4.48% | 1.2240 | 3.38% | 1.7380 | 1.94% |
Derivative 67 | 9.4460 | 11.65% | 1.2440 | 5.07% | 1.7430 | 2.23% |
Derivative 68 | 9.5880 | 13.33% | 1.5060 | 27.20% | 1.7430 | 2.23% |
Derivative 69 | 9.3150 | 10.11% | 1.5320 | 29.39% | 1.7400 | 2.05% |
Derivative 70 | 9.2440 | 9.27% | 1.5460 | 30.57% | 1.7350 | 1.76% |
Levofloxacin | 7.9750 | 1.4590 | 1.7070 | |||
Derivative 71 | 8.9340 | 12.03% | 1.5280 | 4.73% | 1.4730 | −13.71% |
Derivative 72 | 8.7350 | 9.53% | 1.4300 | −1.99% | 1.4750 | −13.59% |
Derivative 73 | 9.0150 | 13.04% | 1.5230 | 4.39% | 1.5320 | −10.25% |
Derivative 74 | 9.3700 | 17.49% | 1.3630 | −6.58% | 1.7120 | 0.29% |
Derivative 75 | 9.0220 | 13.13% | 1.4800 | 1.44% | 1.6800 | −1.58% |
Derivative 76 | 8.4140 | 5.50% | 1.5220 | 4.32% | 1.4980 | −12.24% |
Derivative 77 | 9.4620 | 18.65% | 1.3840 | −5.14% | 1.4730 | −13.71% |
Derivative 78 | 8.9870 | 12.69% | 1.6650 | 14.12% | 1.4560 | −14.70% |
Derivative 79 | 9.0140 | 13.03% | 1.2830 | −12.06% | 1.5410 | −9.72% |
Derivative 80 | 8.7330 | 9.50% | 1.5340 | 5.14% | 1.5350 | −10.08% |
Derivative 81 | 8.5510 | 7.22% | 1.6340 | 11.99% | 1.7030 | −0.23% |
Derivative 82 | 8.1340 | 1.99% | 1.5160 | 3.91% | 1.4660 | −14.12% |
Derivative 83 | 9.1820 | 15.13% | 1.6460 | 12.82% | 1.4190 | −16.87% |
Derivative 84 | 8.4940 | 6.51% | 1.5230 | 4.39% | 1.4390 | −15.70% |
Derivative 85 | 8.9160 | 11.80% | 1.5790 | 8.22% | 1.4700 | −13.88% |
Derivative 86 | 8.8460 | 10.92% | 1.5280 | 4.73% | 1.4610 | −14.41% |
Derivative 87 | 7.9940 | 0.24% | 1.5970 | 9.46% | 1.5430 | −9.61% |
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Li, X.; Zhang, B.; Huang, W.; Cantwell, C.; Chen, B. Integration of Fuzzy Matter-Element Method and 3D-QSAR Model for Generation of Environmentally Friendly Quinolone Derivatives. Int. J. Environ. Res. Public Health 2020, 17, 3239. https://doi.org/10.3390/ijerph17093239
Li X, Zhang B, Huang W, Cantwell C, Chen B. Integration of Fuzzy Matter-Element Method and 3D-QSAR Model for Generation of Environmentally Friendly Quinolone Derivatives. International Journal of Environmental Research and Public Health. 2020; 17(9):3239. https://doi.org/10.3390/ijerph17093239
Chicago/Turabian StyleLi, Xixi, Baiyu Zhang, Wendy Huang, Cuirin Cantwell, and Bing Chen. 2020. "Integration of Fuzzy Matter-Element Method and 3D-QSAR Model for Generation of Environmentally Friendly Quinolone Derivatives" International Journal of Environmental Research and Public Health 17, no. 9: 3239. https://doi.org/10.3390/ijerph17093239