TABLE 2.

NMR spectroscopy data for 2-MIB and 2-MIB biotransformation products^a

C/H	2-MIB			T1 metabolite 3-OH-2-MIB			G1 metabolite 6-OH-2-MIB			DLC-cam metabolite 5-keto-2-MIB
	Type	δ 1H	δ 13C	Type	δ 1H	δ 13C	Type	δ 1H	δ 13C	Type	δ 1H	δ 13C
1	Q		52.8	Q		52.1	Q		56	Q		52.8
2	Q		77.6	Q		79.3	Q		77	Q		76.5
3-exo	CH2	1.91	47.5	CH	4.03	79.2	CH2	1.86	46.4	CH2	2.16	41.5
3-endo		1.22						1.11			1.41
4	CH	1.58	44.9	CH	1.6	50	CH	1.66	45	CH	2.04	60.6
5-exo	CH2	1.59	26.7	CH2	1.64	17	CH2	1.55	39	C=O		215.5
5-endo		0.94			1.25			1.49
6-exo	CH2	1.29	31	CH2	1.24	31.2	CH		72.5	CH2	2.05	45.2
6-endo		1.29			1.24			3.7			1.84
7	CH3	0.78	21.3	CH3	0.82	21.2	CH3	0.99	22.8	CH3	0.85	21.6
8	Q		48.5	Q		45.4	Q		48.3	Q		48
9	CH3	1.04	21.6	CH3	1.1	21.4	CH3	1.05	23.3	CH3	1.17	20.1
10	CH3	0.74	10.2	CH3	0.74	11	CH3	0.77	6.02	CH3	0.89	9.6
2-CH3	CH3	1.11	27.1	CH3	0.98	20.8	CH3	1.07	26.7	CH3	1.14	26.2
2-OH		3.96			3.99			4.5			4.52
3-OH					4.47
6-OH								3.96

^aMolecules with numbered carbons are shown in Fig. 1. These data are from 1D carbon and 1D proton spectra. DEPT 45, DEPT 90, and DEPT 135 spectra were used to define carbon types as methyl, methylene, methine, or quaternary. Additional HMQC, HMBC, COSY, and NOESY spectra contributed to assignments.