<p>Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2016 </p><p><strong>Discovery of Anti-Ebola Drugs: A Computational Drug Repositioning Case Study </strong></p><p>Prashant S. Kharkar<sup style="top: -0.303em;">1</sup>*, Ponnadurai Ramasami<sup style="top: -0.303em;">2</sup>, Yee Siew Choong<sup style="top: -0.303em;">3</sup>, Lydia Rhyman<sup style="top: -0.303em;">2 </sup>and Sona <br>Warrier<sup style="top: -0.303em;">1 </sup><br><sup style="top: -0.303em;">1</sup>SPP School of Pharmacy and Technology Management, SVKM’s NMIMS, <br>V. L. Mehta Road, Vile Parle (West), Mumbai-400 056. INDIA. <br><sup style="top: -0.303em;">2 </sup>Computational Chemistry Group, Department of Chemistry, Faculty of Science, <br>University of Mauritius, Réduit 80837, Mauritius <br><sup style="top: -0.303em;">3</sup>Institute for Research in Molecular Medicine (INFORMM), Universiti Sains Malaysia, <br>Malaysia </p><p><strong>Contents </strong></p><ul style="display: flex;"><li style="flex:1"><strong>Sr. No. </strong></li><li style="flex:1"><strong>Description </strong></li></ul><p></p><p>Table 1S </p><p><strong>Page No. </strong></p><p>123456<br>1<br>Figure 1S Figure 2S Figure 3S Figure 4S Figure 5S <br>28 29 30 31 32 <br><strong>Table 1S. </strong>Top hits (#100) identified from EON screening using query <strong>1 </strong></p><p><strong>Estimated Free Energy of Binding (kcal/mol) </strong><br><strong>Sr. No. </strong><br><strong>EON_ Shape Tanimoto </strong><br><strong>Structure </strong></p><ul style="display: flex;"><li style="flex:1"><strong>Drug </strong></li><li style="flex:1"><strong>ET_pb ET_coul ET_combo </strong></li><li style="flex:1"><strong>Rank </strong></li></ul><p></p><p>OH <br>O<br>Br </p><p>N<br>O</p><p>S</p><p></p><ul style="display: flex;"><li style="flex:1">1</li><li style="flex:1">1</li><li style="flex:1">-9.88 </li></ul><p></p><p>O<br>HO </p><p>OO<br>O<br>S</p><p>O<br>S</p><p></p><ul style="display: flex;"><li style="flex:1">2</li><li style="flex:1">Sitaxentan </li><li style="flex:1">0.633 </li><li style="flex:1">0.914 </li><li style="flex:1">0.926 </li><li style="flex:1">0.294 </li><li style="flex:1">1</li><li style="flex:1">-14.37 </li></ul><p></p><p>HN <br>O</p><p>Cl <br>ON</p><p>O<br>HO </p><p></p><ul style="display: flex;"><li style="flex:1">3</li><li style="flex:1">Alitretinoin<sup style="top: -0.303em;">a </sup></li><li style="flex:1">0.66 </li><li style="flex:1">0.91 </li><li style="flex:1">0.906 </li><li style="flex:1">0.246 </li><li style="flex:1">2</li><li style="flex:1">-3.91 </li></ul><p></p><p>NH<sub style="top: 0.1717em;">2 </sub><br>S</p><p>N</p><p>N<br>O</p><p>O<br>HN </p><p>O<br>S</p><p></p><ul style="display: flex;"><li style="flex:1">4</li><li style="flex:1">Ceftriaxone </li><li style="flex:1">0.606 </li><li style="flex:1">0.937 </li><li style="flex:1">0.823 </li><li style="flex:1">0.217 </li><li style="flex:1">3</li><li style="flex:1">-12.33 </li></ul><p></p><p>N</p><ul style="display: flex;"><li style="flex:1">S</li><li style="flex:1">N</li><li style="flex:1">O</li></ul><p>O</p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">O</li></ul><p>N<br>NH</p><p>O</p><p>56<br>Acitretin<sup style="top: -0.303em;">a </sup>Cidofovir <br>0.637 0.473 <br>0.936 0.633 <br>0.809 0.783 <br>0.172 <br>0.31 <br>45<br>-3.71 -4.21 </p><p>O<br>OH </p><p>HO O<br>NH<sub style="top: 0.1486em;">2 </sub><br>HO </p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p>P<br>HO <br>O<br>O</p><p>NN<br>N<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">7</li><li style="flex:1">Telmisartan </li><li style="flex:1">0.601 </li><li style="flex:1">0.908 </li><li style="flex:1">0.775 </li><li style="flex:1">0.174 </li><li style="flex:1">6</li><li style="flex:1">-6.46 </li></ul><p></p><p>OH <br>O</p><p>Nateglinide<sup style="top: -0.303em;">a </sup>Ceftizoxime </p><ul style="display: flex;"><li style="flex:1">0.54 </li><li style="flex:1">0.874 </li></ul><p>0.88 <br>0.745 0.735 <br>0.205 0.178 <br>78<br>-3.78 </p><p>HN O</p><p>89</p><p>OH <br>O</p><p>H<sub style="top: 0.1489em;">2 </sub></p><p>N<br>S<br>OH </p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">O</li></ul><p>O<br>N<br>S<br>O</p><p></p><ul style="display: flex;"><li style="flex:1">0.557 </li><li style="flex:1">-11.35 </li></ul><p></p><p>NH<br>O<br>N</p><p>OH <br>O<br>O</p><p></p><ul style="display: flex;"><li style="flex:1">10 </li><li style="flex:1">Treprostinil </li><li style="flex:1">0.432 </li><li style="flex:1">0.846 </li><li style="flex:1">0.732 </li><li style="flex:1">0.301 </li><li style="flex:1">9</li><li style="flex:1">-3.41 </li></ul><p></p><p>O<br>HO </p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li></ul><p>S<br>N</p><p>OH <br>S</p><p>11 12 <br>Tenoxicam Dicoumarol <br>0.367 0.368 <br>0.817 0.615 </p><ul style="display: flex;"><li style="flex:1">0.71 </li><li style="flex:1">0.343 </li></ul><p>0.295 <br>10 11 <br>-7.86 -6.06 </p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">HN </li></ul><p>N</p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p>O</p><p>0.663 </p><p>OH </p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">Cl </li></ul><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">Cl </li></ul><p>HO </p><p>13 14 <br>Ethacrynic acid Chlorambucil<sup style="top: -0.303em;">a </sup><br>0.478 0.466 <br>0.847 0.867 <br>0.656 0.646 <br>0.177 <br>0.18 <br>12 13 <br>-4.13 -3.14 </p><p>O</p><p>O</p><ul style="display: flex;"><li style="flex:1">Cl </li><li style="flex:1">OH </li></ul><p>N<br>Cl </p><p>O<br>S</p><p>HO <br>N</p><p></p><ul style="display: flex;"><li style="flex:1">NH </li><li style="flex:1">OH </li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">15 </li><li style="flex:1">Ticarcillin </li><li style="flex:1">0.52 </li><li style="flex:1">0.664 </li><li style="flex:1">0.643 </li><li style="flex:1">0.123 </li><li style="flex:1">14 </li><li style="flex:1">-17.89 </li></ul><p></p><p>O</p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li></ul><p>S</p><p>OH <br>N</p><p>16 17 <br>Nitroxoline Nedocromil </p><ul style="display: flex;"><li style="flex:1">0.41 </li><li style="flex:1">0.824 </li></ul><p>0.603 <br>0.641 0.637 <br>0.232 0.316 <br>15 16 <br>-5.31 <br>-4.2 </p><p>N<sup style="top: -0.2978em;">+ </sup></p><p>O</p><p>O<sup style="top: -0.3492em;">– </sup></p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li></ul><p>O</p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">OH </li></ul><p></p><p>0.321 </p><p>N</p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li></ul><p></p><p>S<br>NH <sub style="top: 0.1621em;">2 </sub></p><p>O</p><p>N</p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">S</li><li style="flex:1">N</li><li style="flex:1">NH </li></ul><p>O<br>O<br>O<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">18 </li><li style="flex:1">Aztreonam </li><li style="flex:1">0.417 </li><li style="flex:1">0.609 </li><li style="flex:1">0.636 </li><li style="flex:1">0.219 </li><li style="flex:1">17 </li><li style="flex:1">-5.13 </li></ul><p></p><p>O<br>O<br>HO </p><p>19 20 <br>Bexarotene<sup style="top: -0.303em;">a </sup>Olmesartan <br>0.381 0.375 <br>0.862 0.593 <br>0.616 0.611 <br>0.235 0.237 <br>18 19 <br>-4.58 -6.28 </p><p>HO <br>O</p><p>N<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">HN </li><li style="flex:1">N</li></ul><p>NO<br>N<br>OH <br>HO </p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p>O</p><p>O</p><p>21 22 <br>Aspartame Cinoxacin <br>0.284 0.313 <br>0.118 0.748 <br>0.605 0.604 <br>0.32 0.29 <br>20 21 <br>-3.59 -5.66 </p><p>O<br>NH </p><p>NH<sub style="top: 0.1299em;">2 </sub></p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li></ul><p>O<br>HO </p><p>N<br>O<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p>HO </p><p></p><ul style="display: flex;"><li style="flex:1">23 </li><li style="flex:1">Minocycline </li><li style="flex:1">0.346 </li><li style="flex:1">0.602 </li><li style="flex:1">0.594 </li><li style="flex:1">0.248 </li><li style="flex:1">22 </li><li style="flex:1">-4.65 </li></ul><p></p><p>H<sub style="top: 0.1703em;">2 </sub></p><p>N<br>OH </p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li><li style="flex:1">OH </li><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">NH<sub style="top: 0.1746em;">2 </sub></li><li style="flex:1">O</li></ul><p>N<br>OH <br>F<br>O</p><p>24 25 26 <br>Sparfloxacin Ceftibuten <br>0.156 <br>0.26 <br>0.061 0.533 0.609 <br>0.591 0.589 0.588 <br>0.435 0.329 0.051 <br>23 24 25 <br>-5.06 <br>-14.71 <br>-4.95 </p><p>N</p><ul style="display: flex;"><li style="flex:1">HN </li><li style="flex:1">F</li></ul><p></p><p>HO <br>O</p><p>N</p><p>H<sub style="top: 0.1126em;">2 </sub></p><p>N<br>NH </p><p>O<br>S<br>S<br>O<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p>O</p><p>OH <br>NH<br>O<br>O</p><p></p><ul style="display: flex;"><li style="flex:1">Pemetrexed </li><li style="flex:1">0.538 </li></ul><p></p><p>N</p><p>H<sub style="top: 0.1586em;">2 </sub></p><p>N<br>HN <br>HN </p><p>F<br>OH <br>HO </p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p>HO </p><p>27 28 <br>Fludarabine Repaglinide<sup style="top: -0.303em;">a </sup><br>0.365 <br>0.41 </p><ul style="display: flex;"><li style="flex:1">0.58 </li><li style="flex:1">0.588 </li></ul><p>0.574 <br>0.223 0.164 <br>26 27 <br>-5.53 -5.61 </p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">NH<sub style="top: 0.1369em;">2 </sub></li></ul><p>N<br>P<br>O<br>HO <br>N<br>O</p><p>O<br>N<br>O<br>OH </p><p>0.832 </p><p>NH<br>O</p><p>O</p><p>H<sub style="top: 0.1375em;">2 </sub></p><p>N</p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p>O</p><p>29 30 <br>Sulfacytine Fluvastatin<sup style="top: -0.303em;">b </sup><br>0.303 0.335 <br>0.768 0.788 <br>0.573 0.568 </p><ul style="display: flex;"><li style="flex:1">0.27 </li><li style="flex:1">28 </li></ul><p>29 <br>-4.09 -3.53 </p><p>S<br>N</p><ul style="display: flex;"><li style="flex:1">H</li><li style="flex:1">O</li></ul><p></p><p>N</p><p>0.233 </p><p>F</p><ul style="display: flex;"><li style="flex:1">OH </li><li style="flex:1">O</li></ul><p></p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">OH </li></ul><p></p><p>HO <br>O<br>O</p><p>N</p><p>31 32 </p><ul style="display: flex;"><li style="flex:1">Ribavirin </li><li style="flex:1">0.216 </li></ul><p>0.46 <br>0.072 0.861 <br>0.561 0.558 <br>0.345 0.098 <br>30 31 <br>-4.52 -3.74 </p><p>OH <br>N</p><p>H<sub style="top: 0.1481em;">2 </sub></p><p>N<br>N<br>OH </p><p>F<br>N</p><p>Pitavastatin </p><p>OH </p><ul style="display: flex;"><li style="flex:1">OH </li><li style="flex:1">OH </li><li style="flex:1">O</li></ul><p></p><p>O<br>OH P</p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">N</li></ul><p>N<br>OH </p><p>F<sub style="top: 0.0875em;">3 </sub></p><p></p><ul style="display: flex;"><li style="flex:1">C</li><li style="flex:1">N</li></ul><p>NH <br>O<br>O</p><p>33 34 </p><ul style="display: flex;"><li style="flex:1">Fosaprepitant </li><li style="flex:1">0.43 </li><li style="flex:1">0.743 </li></ul><p>0.144 <br>0.552 0.544 <br>0.121 0.268 <br>32 33 <br>-5.64 -5.47 </p><p>CF <sub style="top: 0.0875em;">3 </sub><br>F</p><p>O<br>OH O<br>N<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">Cilazapril </li><li style="flex:1">0.276 </li></ul><p></p><p>NH <br>O<br>O</p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p></p><p>H<sub style="top: 0.1477em;">2 </sub></p><p>N<br>O<br>N</p><p>35 36 </p><ul style="display: flex;"><li style="flex:1">Tenofovir<sup style="top: -0.303em;">c </sup></li><li style="flex:1">0.373 </li></ul><p>0.285 <br>0.611 0.752 <br>0.543 0.536 </p><ul style="display: flex;"><li style="flex:1">0.17 </li><li style="flex:1">34 </li></ul><p>35 <br>-5.65 -5.07 </p><p>O<br>OH <br>N<br>P</p><p>OH </p><p>Cl <br>O</p><p>O</p><p></p><ul style="display: flex;"><li style="flex:1">Atovaquone </li><li style="flex:1">0.251 </li></ul><p></p><p>HO </p><p>HN<br>O<br>O<br>S</p><p>O</p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p></p><p>37 38 <br>Sulfadimethoxine <br>Cyclacillin </p><ul style="display: flex;"><li style="flex:1">0.28 </li><li style="flex:1">0.746 </li></ul><p>0.127 <br>0.536 0.531 <br>0.256 0.341 <br>36 37 <br>-4.39 </p><p>NH<sub style="top: 0.1475em;">2 </sub><br>O</p><p>HO <br>O<br>O<br>N<br>O</p><p>S</p><p>H<sub style="top: 0.1789em;">2 </sub></p><p>N</p><p></p><ul style="display: flex;"><li style="flex:1">0.189 </li><li style="flex:1">-14.26 </li></ul><p></p><p>NH </p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">OH </li><li style="flex:1">Cl </li></ul><p>HO </p><p>39 40 <br>Demeclocycline Fosphenytoin <br>0.223 0.395 <br>0.523 0.593 </p><ul style="display: flex;"><li style="flex:1">0.53 </li><li style="flex:1">0.306 </li></ul><p>0.134 <br>38 39 <br>-4.44 <br>-5.3 </p><p>O<br>OH </p><ul style="display: flex;"><li style="flex:1">NH<sub style="top: 0.1813em;">2 </sub></li><li style="flex:1">O</li><li style="flex:1">OH </li><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p></p><p>HO O<br>OH <br>O</p><p>P</p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">O</li></ul><p></p><p>0.529 </p><p>HN <br>O</p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p>HO </p><p>H<sub style="top: 0.1783em;">2 </sub></p><p>N<br>NH <br>OH </p><p></p><ul style="display: flex;"><li style="flex:1">41 </li><li style="flex:1">Tigecycline </li><li style="flex:1">0.314 </li><li style="flex:1">0.688 </li><li style="flex:1">0.528 </li><li style="flex:1">0.214 </li><li style="flex:1">40 </li><li style="flex:1">-5.24 </li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li><li style="flex:1">OH </li><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p>O</p><p>HN </p><p>HO <br>O</p><p>42 43 44 <br>Fosfomycin Penicillin V Sulfadoxine <br>0.322 0.394 0.261 <br>0.57 <br>0.804 0.735 <br>0.526 0.518 0.516 <br>0.204 0.125 0.254 <br>41 42 43 <br>-4.1 <br>-8.79 -4.37 </p><p>P<br>HO <br>O</p><p>HN<br>S<br>O<br>N<br>O</p><p>O<br>O</p><p>OH </p><p>O<br>HN<br>O<br>O<br>S</p><p>O</p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p>NH<sub style="top: 0.1473em;">2 </sub></p><p>N</p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li><li style="flex:1">O</li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">45 </li><li style="flex:1">Tasosartan </li><li style="flex:1">0.396 </li><li style="flex:1">0.733 </li><li style="flex:1">0.515 </li><li style="flex:1">0.12 </li><li style="flex:1">44 </li><li style="flex:1">-7.76 </li></ul><p></p><p>NN<br>N<br>NH </p><p>OH <br>HO <br>OH </p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">HN </li></ul><p>O<br>N</p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li></ul><p>N</p><p>N</p><p>46 47 </p><ul style="display: flex;"><li style="flex:1">Regadenoson </li><li style="flex:1">0.168 </li></ul><p>0.208 <br>0.054 0.518 <br>0.514 0.514 <br>0.346 0.306 <br>45 46 <br>-5.17 -3.83 </p><p>N<br>NH<sub style="top: 0.1302em;">2 </sub></p><p></p><ul style="display: flex;"><li style="flex:1">OH </li><li style="flex:1">N</li></ul><p>OH </p><p>OH </p><p>O</p><p>Oxytetracycline </p><p>NH<sub style="top: 0.1255em;">2 </sub><br>OH </p><ul style="display: flex;"><li style="flex:1">OH </li><li style="flex:1">O</li><li style="flex:1">OH </li><li style="flex:1">O</li></ul><p></p><p>N<br>N</p><p>N</p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">N</li><li style="flex:1">NH </li></ul><p></p><p>48 49 <br>Pazopanib Captopril </p><ul style="display: flex;"><li style="flex:1">0.25 </li><li style="flex:1">0.081 </li><li style="flex:1">0.506 </li></ul><p>0.506 <br>0.257 0.175 <br>47 48 <br>-7.35 </p><p>OS</p><p>H<sub style="top: 0.1299em;">2 </sub></p><p>N<br>O</p><p>SH <br>O<br>O</p><p></p><ul style="display: flex;"><li style="flex:1">0.331 </li><li style="flex:1">0.8 </li><li style="flex:1">-16.74 </li></ul><p></p><p>N<br>HO </p><p>Cl <br>O<br>O</p><p>S</p><p>50 51 <br>Chlorpropamide <br>Furosemide <br>0.263 0.269 </p><ul style="display: flex;"><li style="flex:1">0.7 </li><li style="flex:1">0.503 </li></ul><p>0.497 </p><ul style="display: flex;"><li style="flex:1">0.24 </li><li style="flex:1">49 </li></ul><p>50 <br>-4.1 </p><p>NH<br>NH<br>O</p><p>O<br>O</p><p>H<sub style="top: 0.1486em;">2 </sub></p><p>N<br>S<br>OH <br>O</p><p></p><ul style="display: flex;"><li style="flex:1">0.758 </li><li style="flex:1">0.228 </li><li style="flex:1">-4.58 </li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">Cl </li><li style="flex:1">N</li></ul><p>H</p><p>O</p><p>OSN<br>F<br>O</p><p>N</p><p>N</p><p>52 53 <br>Rosuvastatin<sup style="top: -0.303em;">b </sup>Sulfamethizole <br>0.41 0.36 <br>0.855 0.763 <br>0.496 0.496 <br>0.086 0.136 <br>51 52 <br>-3.05 -5.27 </p><p>OH </p><ul style="display: flex;"><li style="flex:1">OH </li><li style="flex:1">OH </li><li style="flex:1">O</li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">S</li><li style="flex:1">N</li></ul><p>O<br>N</p><p>H<sub style="top: 0.1982em;">2 </sub></p><p>N<br>S<br>NH </p><p>O</p><p>OH <br>O<br>P<br>HO <br>OH </p><p>O<br>P</p><p>54 55 </p><ul style="display: flex;"><li style="flex:1">Zoledronate </li><li style="flex:1">0.135 </li></ul><p>0.356 <br>0.268 0.761 <br>0.496 0.493 <br>0.361 0.136 <br>53 54 <br>-4.38 <br>-4.1 </p><p>OH NN<br>HO </p><p>O<br>HN </p><p>O</p><ul style="display: flex;"><li style="flex:1">S</li><li style="flex:1">NH<sub style="top: 0.147em;">2 </sub></li></ul><p></p><p>Sulfacetamide </p><p>O</p><p>OH <br>OH </p><p>HO </p><p>56 57 </p><ul style="display: flex;"><li style="flex:1">Ascorbic acid<sup style="top: -0.303em;">d </sup></li><li style="flex:1">0.231 </li></ul><p>0.366 <br>0.758 0.808 <br>0.492 0.486 </p><ul style="display: flex;"><li style="flex:1">0.262 </li><li style="flex:1">55 </li></ul><p>56 <br>-2.86 </p><p>O</p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">HO </li></ul><p></p><p>HO <br>O</p><p>O<br>N<br>O</p><p>S<br>NH </p><p></p><ul style="display: flex;"><li style="flex:1">Azidocillin </li><li style="flex:1">0.12 </li><li style="flex:1">-13.11 </li></ul><p></p><p>N</p><p>+</p><p>N</p><p>–</p><p>N</p><p>OH <br>O</p><p>58 59 </p><ul style="display: flex;"><li style="flex:1">Naproxen </li><li style="flex:1">0.28 </li><li style="flex:1">0.77 </li></ul><p>0.75 <br>0.486 <br>0.48 <br>0.206 0.138 <br>57 58 <br>-3.87 -6.59 </p><p>O</p><p>H<sub style="top: 0.1186em;">2 </sub></p><p>N<br>OS</p><p>S<br>NH <br>O</p><p></p><ul style="display: flex;"><li style="flex:1">Sulfathiazole </li><li style="flex:1">0.343 </li></ul><p></p><p>N</p><p>O</p><p>60 61 <br>Beclomethasone<sup style="top: -0.303em;">a </sup><br>Cefacetrile </p><p>HO </p><p>0.139 0.246 <br>0.011 0.724 <br>0.479 0.477 <br>0.341 0.231 <br>59 60 <br>-3.45 -8.14 </p><p>Cl OH <br>HO </p><p>O</p><p>O</p><p>OH <br>O<br>O<br>O<br>N<br>N</p><p>O<br>NH<br>S</p><p>NH<sub style="top: 0.1869em;">2 </sub><br>S</p><p>N</p><p>N<br>O</p><p>O<br>HN </p><p>O<br>S</p><p></p><ul style="display: flex;"><li style="flex:1">62 </li><li style="flex:1">Cefmenoxime </li><li style="flex:1">0.276 </li><li style="flex:1">0.741 </li><li style="flex:1">0.476 </li><li style="flex:1">0.2 </li><li style="flex:1">61 </li><li style="flex:1">-8.23 </li></ul><p></p><p>N<br>S<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">O</li></ul><p>N</p><p>N<br>N</p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">O</li></ul><p>N</p><p></p><ul style="display: flex;"><li style="flex:1">63 </li><li style="flex:1">Entacapone </li><li style="flex:1">0.301 </li><li style="flex:1">0.748 </li><li style="flex:1">0.473 </li><li style="flex:1">0.172 </li><li style="flex:1">62 </li><li style="flex:1">-4.87 </li></ul><p></p><p>O<sup style="top: -0.3845em;">– </sup></p><p>+</p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">OH </li></ul><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">OH </li></ul><p></p><p>N<br>OH </p><p>OH </p><p>O</p><p>64 65 </p><ul style="display: flex;"><li style="flex:1">Tetracycline </li><li style="flex:1">0.212 </li></ul><p>0.224 <br>0.514 0.525 <br>0.472 0.472 </p><ul style="display: flex;"><li style="flex:1">0.26 </li><li style="flex:1">63 </li></ul><p>64 <br>-4.58 -4.04 </p><p>NH<sub style="top: 0.1255em;">2 </sub><br>OH </p><p>O</p><p></p><ul style="display: flex;"><li style="flex:1">OH </li><li style="flex:1">O</li><li style="flex:1">OH </li><li style="flex:1">O</li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">OH </li><li style="flex:1">O</li><li style="flex:1">OH </li><li style="flex:1">OH </li></ul><p>OH </p><p></p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">N</li></ul><p>H</p><p></p><ul style="display: flex;"><li style="flex:1">Clomocycline </li><li style="flex:1">0.248 </li></ul><p></p><p>O<br>HO </p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">Cl </li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">O</li><li style="flex:1">O</li></ul><p></p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">N</li></ul><p>H</p><p>N<br>N</p><p>66 67 </p><ul style="display: flex;"><li style="flex:1">Balsalazide </li><li style="flex:1">0.34 </li><li style="flex:1">0.602 </li></ul><p>0.735 <br>0.472 0.471 <br>0.132 0.214 <br>65 66 <br>-4.57 </p><p>OH </p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">O</li></ul><p></p><p>SO<br>HN <br>S</p><p></p><ul style="display: flex;"><li style="flex:1">Cefalotin </li><li style="flex:1">0.258 </li><li style="flex:1">-13.17 </li></ul><p></p><p></p><ul style="display: flex;"><li style="flex:1">N</li><li style="flex:1">O</li></ul><p>O<br>O</p><ul style="display: flex;"><li style="flex:1">HO </li><li style="flex:1">O</li></ul><p></p><p>OH </p><p>68 69 </p><ul style="display: flex;"><li style="flex:1">Ethynodiol<sup style="top: -0.303em;">a </sup></li><li style="flex:1">0.071 </li></ul><p>0.348 <br>0.011 0.761 <br>0.471 0.469 </p><ul style="display: flex;"><li style="flex:1">0.4 </li><li style="flex:1">67 </li></ul><p>68 <br>-4.9 </p><p>HO </p><p>ON<br>NH <br>O<br>S</p><p></p><ul style="display: flex;"><li style="flex:1">Sulfamethoxzole </li><li style="flex:1">0.121 </li><li style="flex:1">-4.62 </li></ul><p></p><p>O</p><p>H<sub style="top: 0.1977em;">2 </sub></p><p>N</p><p>HO <br>O</p><p>Epoprostenol<sup style="top: -0.303em;">a </sup>Gemfibrozil<sup style="top: -0.303em;">a </sup><br>0.123 0.378 <br>0.599 0.804 <br>0.468 0.467 <br>0.345 0.089 <br>69 70 <br>-3.69 -3.29 </p><p>OH </p><p>70 71 </p><p>OH <br>O</p><p>O<br>O</p><p>HO </p><p>N<br>O</p><p>S<br>O</p><p>72 73 <br>Sulfisoxazole Amdinocillin <br>0.348 0.246 <br>0.755 0.102 <br>0.466 0.466 <br>0.119 0.219 <br>71 72 <br>-5.03 </p>