Table 2. Ligand–MOR Interaction Pharmacophores Inferred from Molecular Docking Solutions of N-Methylmorphinan-6-ones 1–4 and Their 6-Desoxo Counterparts 1a–4a.

	hydrophobic interactions		hydrogen bonds
compd	inferred from phenol	inferred from introduced group	charge-enhanced hydrogen bond	interactions mediated by water molecules
1	M151, V236, I296, V300	NDa	D147	H297
1a	M151, V236, I296, V300	NDa	D147	H297
2	M151, V236, I296, V300	NDa	D147	H297
2a	M151, V236, I296, V300	NDa	D147	H297
3	M151, V236, I296, V300	I144b	D147	H297
3a	M151, V236, I296, V300	I144b	D147	H297
4	M151, V236, I296, V300	NDa	D147	H297
4a	M151, V236, I296, V300	Y148c	D147	H297

^aND, not deduced.

^bFormed by the 14-benzyloxy group.

^cFormed by the 5-methyl group.