Table 3. Results from MD Trajectories Inspecting the Propensity To Form Intermolecular Hydrogen Bonds of Oxymorphone (1) and the Investigated 14-Oxygenated N-Methylmorphinan-6-ones (2–6).
| basic nitrogen |
4,5α-epoxy group | 3-phenol group |
|||||
|---|---|---|---|---|---|---|---|
| ligand | D147 | Y326 | Y148 | H54 | Y148 | K233 | K303 |
| OM (1)a | 82% | 4% | 0% | 82% | 0% | 0% | 60% |
| 14-OMO (2a) | 78% | 40% | 20% | 0% | 0% | 0% | 0% |
| 14-MM (2b) | 82% | 32% | 6% | 0% | 0% | 0% | 0% |
| 14-OEO (3a) | 76% | 18% | 2% | 0% | 0% | 0% | 0% |
| 14-EM (3b) | 86% | 14% | 0% | 0% | 0% | 0% | 0% |
| 14-OBO (4a) | 46% | 18% | 8% | 0% | 0% | 0% | 0% |
| 14-BM (4b) | 80% | 8% | 0% | 0% | 0% | 0% | 0% |
| PPOM (5) | 56% | 26% | 10% | 0% | 6% | 2% | 0% |
| BOMO (6) | 16% | 74% | 34% | 0% | 38% | 4% | 0% |
a
Truncated, as intermolecular hydrogen bonds formed by the 14-hydroxyl group are not included (as this moiety is unique to OM and not present in the other molecules of the investigated morphinan class).