## 3 Results
### In Silico Evaluation of Reference Compounds by Docking Simulations
\begin{table}
\begin{tabular}{c c c c c} \hline \hline
**Ligand** & **Score*** & **RMSD** & **Hydrogen Bond** & **Length (Å)** \\ \hline Co-crystallized 3J5 & & & & O1 sp\({}^{3}\)-Osp\({}^{2}\) GLU1291 & 3.393 \\ (2-(4-[6-[(3S)-3,4-dimethylpiperazin-1-yl]- & \(-\)104.15 & 0.16 & O1 sp\({}^{3}\)–Osp\({}^{2}\) GLU1291 & 3.250 \\
4-methylpyridin-3-yl]phenyl)-8- & & & O sp\({}^{2}\)–Osp\({}^{3}\) SER1221 & 2.778 \\ (hydroxymethyl)quinazolin-4(3H)-one) & & & O sp\({}^{2}\)–Nsp\({}^{2}\) GLY1185 & 2.895 \\ \hline \multirow{6}{*}{Luteolin-7-O-glucose} & \multirow{6}{*}{\(-80.49\)} & \multirow{6}{*}{0.69} & O10 sp\({}^{3}\)–Osp\({}^{2}\) GLY1196 & 3.284 \\  & & & O10 sp\({}^{3}\)–Nsp\({}^{2}\) ASP1198 & 2.729 \\  & & & O11 sp\({}^{3}\)–Nsp\({}^{2}\) ASP1198 & 2.741 \\  & & & O11 sp\({}^{3}\)–Osp\({}^{2}\) ASP1198 & 3.067 \\  & & & O5 sp\({}^{3}\)–Osp\({}^{2}\) GLY1185 & 2.456 \\  & & & O3 sp\({}^{3}\)–Osp\({}^{2}\) GLY1185 & 3.090 \\  & & & O3 sp\({}^{3}\)–Nsp\({}^{2}\) GLY1185 & 2.647 \\  & & & O3 sp\({}^{3}\)–Osp\({}^{3}\) SER1221 & 3.040 \\  & & & O4 sp\({}^{3}\)–Osp\({}^{3}\) SER1221 & 3.087 \\  & & & O4 sp\({}^{3}\)–Nsp\({}^{2}\) SER1221 & 3.298 \\ \hline \multirow{6}{*}{Luteolin-8-C-glucose} & \multirow{6}{*}{\(-61.88\)} & \multirow{6}{*}{0.02} & O11 sp\({}^{3}\)–Nsp\({}^{2}\) ASP1198 & 2.992 \\  & & & O9 sp\({}^{2}\)–Nsp\({}^{2}\) TR1213 & 3.034 \\  & & & O4 sp\({}^{3}\)–Nsp\({}^{2}\) HIS1201 & 2.920 \\  & & & O3 sp\({}^{3}\)–Osp\({}^{2}\) ALA1202 & 3.129 \\  & & & O6 sp\({}^{3}\)–Nsp\({}^{2}\) HIS1201 & 2.817 \\ \hline \multirow{6}{*}{Caffeic acid} & \multirow{6}{*}{\(-58.55\)} & \multirow{6}{*}{0.15} & O3 sp\({}^{3}\)–Osp\({}^{3}\) TYR1224 & 3.050 \\  & & & O3 sp\({}^{3}\)–Osp\({}^{2}\) GLU1291 & 2.912 \\  & & & O2 sp\({}^{3}\)–Nsp\({}^{2}\) TYR1213 & 3.364 \\  & & & O2 sp\({}^{3}\)–Nsp\({}^{2}\) HIS1184 & 3.089 \\  & & & O2 sp\({}^{3}\)–Nsp\({}^{2}\) GLY1185 & 2.925 \\  & & & O2 sp\({}^{3}\)–Osp\({}^{2}\) GLY1185 & 3.022 \\ \hline \multirow{6}{*}{Gentisic acid} & \multirow{6}{*}{\(-51.02\)} & \multirow{6}{*}{0.01} & O1 sp\({}^{3}\)–Osp\({}^{3}\) TYR1224 & 3.142 \\  & & & O0 sp\({}^{3}\)–Osp\({}^{2}\) TYR1213 & 3.212 \\  & & & O0 sp\({}^{3}\)–Osp\({}^{3}\) SER1221 & 2.880 \\  & & & O2 sp\({}^{3}\)–Nsp\({}^{2}\) HIS1184 & 3.196 \\  & & & O2 sp\({}^{3}\)–Nsp\({}^{2}\) GLY1185 & 3.123 \\  & & & O2 sp\({}^{3}\)–Osp\({}^{2}\) GLY1185 & 2.829 \\ \hline \multirow{6}{*}{p-aminobenzoic acid} & \multirow{6}{*}{\(-49.16\)} & \multirow{6}{*}{0.17} & N2 sp\({}^{3}\)–Osp\({}^{3}\) TYR1224 & 3.092 \\  & & & O0 sp\({}^{3}\)–Osp\({}^{2}\) TYR1213 & 3.087 \\  & & & O0 sp\({}^{3}\)–Nsp\({}^{2}\) ALA1225 & 3.270 \\  & & & O0 sp\({}^{3}\)–Osp\({}^{3}\) SER1221 & 2.678 \\  & & & O0 sp\({}^{3}\)–Osp\({}^{2}\) PHE1183 & 2.989 \\  & & & O1 sp\({}^{2}\)–Nsp\({}^{2}\) HIS1184 & 3.037 \\  & & & O1 sp\({}^{2}\)–Nsp\({}^{2}\) GLY1185 & 3.001 \\ \hline \hline \end{tabular}  
* The docking score used in the DDW is the PLANTS\({}_{\text{PLP}}\) score [46] that considers all type of contributions of heavy atom contacts (inter atom distance less than 5.5 Å) between ligand and the binding site (hydrogen bond interactions, lone-pair-metal ion interactions, non-polar interactions, non-polar contacts, repulsive contacts), evaluating the potential energy change at the formation of the protein-ligand complex. Consequently, a negative score corresponds to a strong binding affinity, while a less negative or positive score means poor or lack of binding.  
\end{table} 
Table 1: Results of molecular docking study on human tankyrase 1 (PDB ID: 4W6E, chain A) [40].