. Author manuscript; available in PMC: 2020 Dec 17.

Published in final edited form as: Anal Chem. 2019 Dec 3;91(24):15686–15693. doi: 10.1021/acs.analchem.9b03849

Table 1.

Examples of molecular structural motif identification of bile metabolites by COLMAR and pNMR MSMMDB queries

Chemical shifts of input (¹H, ¹³C) spin pairs	Hit that contains true motif returned by COLMAR MSMMDB (Hit rank, type of identified true motif, RMSD (ppm))	Hit that contains true motif returned by pNMR MSMMDB (Hit rank, type of identified true motif, RMSD (ppm))	True Metabolite
(4.120, 86.907) (4.342, 76.337) (4.213, 72.108) (3.802, 63.425) (3.918, 63.385) (5.902, 92.079)	5-Methyluridine (1, 2^nd shell, 0.16)	Beta-D-3-Ribofuranosyluric acid (2, 2^nd shell, 2.08)	Uridine
(7.183, 133.486) (6.888, 118.557)	3-Chlorotyrosine (1, 2^nd shell, 0.20)	N-(1-Deoxy-1-fructosyl)tyrosine (1, 2^nd shell, 1.42)	L-tyrosine
(3.768, 74.784) (3.632, 65.208) (3.610, 73.570)	Adonitol (1, 2^nd shell, 0.79)	Xylitol (1, 2^nd shell, 1.80)	Xylitol
(1.788, 33.111) (2.996, 41.918) (4.135, 57.765) (1.710, 29.096) (1.398, 24.725)	Biocytin (1, 1^st shell, 1.29)	N6-L-homocysteinyl-N2-L-valyl-L-lysine (3, ^*2^nd shell, 1.29)	Aspartyl-lysine
(3.966, 62.877) (3.234, 43.195)	Ethanolamine (1, 1^st shell, 1.63)	Phosphoethanolamine (1, 2^nd shell, 1.44)	Phosphoethanolamine
(4.243, 68.598) (3.575, 63.141) (1.318, 22.145)	O-phosphothreonine (l, ^*2^nd shell, 1.64)	Cyclic N(6)-threonylcarbamoyladenosine (1, 2^nd shell, 1.83)	Threonine

For these molecules, a partial 2^nd shell MSM was identified, since in the true molecule a hydrogen terminates the 1^st shell MSM.