Table 2. Ligand/μ-OR Interaction Pharmacophores Inferred from Molecular Docking Solutions of Oxymorphone (1) and the Investigated 14-Oxygenated N-Methylmorphinan-6-ones (2–6).
| hydrophobic
interactions |
hydrogen bonds |
|||
|---|---|---|---|---|
| ligand | inferred from the phenol | inferred from the introduced group | charge-enhanced hydrogen bond | interactions mediated by water molecules |
| OM (1) | M151, V236, I296, V300 | NDa | D147 | H297 |
| 14-OMO (2a) | M151, V236, I296, V300 | ND | D147 | H297 |
| 14-MM (2b) | M151, V236, I296, V300 | ND | D147 | H297 |
| 14-OEO (3a) | M151, V236, I296, V300 | ND | D147 | H297 |
| 14-EM (3b) | M151, V236, I296, V300 | I322 | D147 | H297 |
| 14-OBO (4a) | M151, V236, I296, V300 | I144 | D147 | H297 |
| 14-BM (4b) | M151, V236, I296, V300 | I144 | D147 | H297 |
| PPOM (5) | M151, V236, I296, V300 | W133, V143, I144 | D147 | H297 |
| BOMO (6) | M151, V236, I296, V300 | I322 | D147 | H297 |
a
ND denotes not deduced.