Table 4

NMR assignments for the metabolites of delavirdine

Proton	MET-4b		MET-4c		MET-16		MET-5
Proton	δ^4-a	COSY^4-b	HETCOR^4-c	δ^4-a	COSY^4-b	HETCOR^4-c	δ^4-a	COSY^4-b	δ^4-a	HETCOR^4-c
Indole ring
H-3	6.83	—	106	6.85	—	105	7.35	—	6.84	105
H-4	7.55	—	116	7.56	—	116			7.56	116
H-6	7.17	7.42	121	7.17	7.43	121	7.32	7.25	7.17	121
H-7	7.42	7.17	113	7.43	7.17	112	7.25	7.32	7.43	112
Pyridine ring
H-4′	7.13	6.91	121	7.17	7.01	121	6.98	7.55	7.09	123
H-5′	6.91	7.13	111	7.01	7.17	122	6.98	7.55	6.90	NO^4-d
H-6′		—	NO^4-d	7.68	—	NO^4-d	7.55	6.98	7.62	NO^4-d
Piperazine ring
CH₂N	3.99	3.19	NO^4-d	4.07	3.03	NO^4-d	4.08	3.09	4.07	NO^4-d
CH₂N	3.19	3.99	53	3.03	4.07	51	3.09	4.08	3.15	50
Isopropyl chain
CH							3.65	1.26
CH₃							1.26	3.65
Methylsulfonate
CH₃SO₂NH	2.88	—	38	2.89	—	38	2.93 (s, 3H)	—	2.89	38
Sugar
H-1"				5.91	4.55	NO^4-d	4.86	3.62
H-2"				4.55	5.91, 4.01	NO^4-d	3.62	4.86, 3.47
H-3"				4.01	4.55, 3.55	NO^4-d	3.47	3.62, 3.54
H-4"				3.55	4.01, 3.44	NO^4-d	3.54	3.47, 3.59
H-5"				3.44	3.55	NO^4-d	3.59	3.54
H-6a"				3.87	3.67	NO^4-d
H-6b"				3.67	3.87	NO^4-d
NHCOCH₃				2.01	—	22

↵4-a Proton chemical shift δ in ppm relative to methanol.
↵4-b COSY, correlation spectroscopy; homonuclear spin coupling observed to the indicated resonance.
↵4-c HETCOR, heteronuclear correlation;¹³C assignments in ppm relative to methanol.
↵4-d NO, not observed with the acquisition parameters used in the experiment.