PMID-sentid	Pub_year	Sent_text	compound_name	comp_offset	prot_official_name	organism	prot_offset
25839944-7	2015	Collectively, our results indicate that a reduction in the basicity of the lower axial ligand causes changes to the cofactor"s electronic structure in the Co(II) state that replicate the effects seen upon binding of Co(II)Cbl to Class I isomerases, which replace the lower axial dimethylbenzimidazole ligand of AdoCbl with a protein-derived histidine (His) residue.	5,6-dimethylbenzimidazole	279-300	mitochondrially encoded cytochrome c oxidase II	Homo sapiens	155-161
26841310-6	2016	Our spectroscopic studies suggest that TsrM binds cobalamin in an uncharacteristic five-coordinate base-off/His-off conformation, whereby the dimethylbenzimidazole group is replaced by a non-nitrogenous ligand, which is likely a water molecule.	5,6-dimethylbenzimidazole	142-163	TSRM	Homo sapiens	39-43
9242908-2	1997	These structures reveal that the B12 cofactor undergoes a major conformational change on binding to the apoenzymes of methionine synthase and methylmalonyl-coenzyme A mutase: The dimethylbenzimidazole ligand to the cobalt is displaced by a histidine residue from the protein.	5,6-dimethylbenzimidazole	179-200	5-methyltetrahydrofolate-homocysteine methyltransferase	Homo sapiens	118-137
22568547-12	2012	The BP86 method shows more spectral features, and the best fit was found for a GS-Cbl model with 5,6-dimethylbenzimidazole at the BP86/6-311G(d,p) level with a water cpcm solvent model.	5,6-dimethylbenzimidazole	97-122	Cbl proto-oncogene	Homo sapiens	82-85
11237251-3	2001	The models of this process show that in both methylcobalamin (CH3Cbl) and AdoCbl, compression of the axial Co-N bond does engender upward folding of the corrin ring, and that the extent of such upward folding is smaller in an analog in which the normal 5,6-dimethylbenzimidazole axial ligand is replaced by the sterically smaller ligand, imidazole (CH3(lm)Cbl and Ado(lm)Cbl).	5,6-dimethylbenzimidazole	253-278	Cbl proto-oncogene	Homo sapiens	77-80
10504238-3	1999	Free dimethylbenzimidazole axial base-on cob(II)alamin was formed by photolysis of the corresponding adenosylcobalamin and cryotrapped in glycerol-aqueous glass.	5,6-dimethylbenzimidazole	5-26	metabolism of cobalamin associated B	Homo sapiens	41-44
10504238-8	1999	The results identify the coenzyme"s on-board dimethylbenzimidazole moiety as the alpha-axial ligand to cob(II)alamin in ethanolamine deaminase in the substrate radical-Co(II) biradical catalytic intermediate state.	5,6-dimethylbenzimidazole	45-66	metabolism of cobalamin associated B	Homo sapiens	103-106
10504238-8	1999	The results identify the coenzyme"s on-board dimethylbenzimidazole moiety as the alpha-axial ligand to cob(II)alamin in ethanolamine deaminase in the substrate radical-Co(II) biradical catalytic intermediate state.	5,6-dimethylbenzimidazole	45-66	mitochondrially encoded cytochrome c oxidase II	Homo sapiens	168-174
10504238-11	1999	A 14% increase in the isotropic hyperfine coupling of the remote dimethylbenzimidazole (14)N nucleus in enzyme-bound versus free base-on cob(II)alamin shows an enhanced delocalization of unpaired spin density from Co(II) onto the axial ligand, which would contribute to the acceleration of the cobalt-carbon bond cleavage rate in situ.	5,6-dimethylbenzimidazole	65-86	metabolism of cobalamin associated B	Homo sapiens	137-140
10504238-11	1999	A 14% increase in the isotropic hyperfine coupling of the remote dimethylbenzimidazole (14)N nucleus in enzyme-bound versus free base-on cob(II)alamin shows an enhanced delocalization of unpaired spin density from Co(II) onto the axial ligand, which would contribute to the acceleration of the cobalt-carbon bond cleavage rate in situ.	5,6-dimethylbenzimidazole	65-86	mitochondrially encoded cytochrome c oxidase II	Homo sapiens	214-220
9722671-7	1998	Upon suicide inactivation with a [15N2]imidazolyl analog, the octet signals due to Co(II) showed superhyperfine splitting into doublets, indicating axial coordination of 5,6-dimethylbenzimidazole to the cobalamin bound to diol dehydratase.	5,6-dimethylbenzimidazole	170-195	mitochondrially encoded cytochrome c oxidase II	Homo sapiens	83-89
25171056-3	2015	In CBL, 5,6-dimethylbenzimidazole (5,6-DMB) is the base in the nucleotide moiety.	5,6-dimethylbenzimidazole	8-33	major histocompatibility complex, class II, DM beta	Bos taurus	39-42
19700356-6	2009	We also report that MMACHC binds CNCbl in the base-off form, with the dimethylbenzimidazole (DMB) base of cobalamin displaced from coordination with the cobalt.	5,6-dimethylbenzimidazole	70-91	metabolism of cobalamin associated C	Homo sapiens	20-26
19700356-6	2009	We also report that MMACHC binds CNCbl in the base-off form, with the dimethylbenzimidazole (DMB) base of cobalamin displaced from coordination with the cobalt.	5,6-dimethylbenzimidazole	93-96	metabolism of cobalamin associated C	Homo sapiens	20-26
14661978-5	2003	These measurements can be used to estimate the influence of the dimethylbenzimidazole ligand on both the thermodynamics and kinetics of methyl transfer between methyltetrahydrofolate and cob(I)alamin or cob(I)inamide.	5,6-dimethylbenzimidazole	64-85	metabolism of cobalamin associated B	Homo sapiens	187-190
14661978-5	2003	These measurements can be used to estimate the influence of the dimethylbenzimidazole ligand on both the thermodynamics and kinetics of methyl transfer between methyltetrahydrofolate and cob(I)alamin or cob(I)inamide.	5,6-dimethylbenzimidazole	64-85	metabolism of cobalamin associated B	Homo sapiens	203-206
10563814-0	1999	Role of the dimethylbenzimidazole tail in the reaction catalyzed by coenzyme B12-dependent methylmalonyl-CoA mutase.	5,6-dimethylbenzimidazole	12-33	methylmalonyl-CoA mutase	Homo sapiens	91-115
9242908-2	1997	These structures reveal that the B12 cofactor undergoes a major conformational change on binding to the apoenzymes of methionine synthase and methylmalonyl-coenzyme A mutase: The dimethylbenzimidazole ligand to the cobalt is displaced by a histidine residue from the protein.	5,6-dimethylbenzimidazole	179-200	methylmalonyl-CoA mutase	Homo sapiens	142-173
33797888-7	2021	In addition, they have revealed the practical utility of the dimethylbenzimidazole tail, an appendage unique to cobalamins and absent in the structural cousins, porphyrin, chlorin, and corphin, as an instrument for facilitating cofactor transfer between active sites.In this Account, we navigate the chemistry of the B12 trafficking pathway from its point of entry into cells, through lysosomes, and into the cytoplasm, where incoming cobalamin derivatives with a diversity of upper ligands are denuded by the beta-ligand transferase activity of CblC to the common cob(II)alamin intermediate.	5,6-dimethylbenzimidazole	61-82	Cbl proto-oncogene C	Homo sapiens	546-550
33797888-7	2021	In addition, they have revealed the practical utility of the dimethylbenzimidazole tail, an appendage unique to cobalamins and absent in the structural cousins, porphyrin, chlorin, and corphin, as an instrument for facilitating cofactor transfer between active sites.In this Account, we navigate the chemistry of the B12 trafficking pathway from its point of entry into cells, through lysosomes, and into the cytoplasm, where incoming cobalamin derivatives with a diversity of upper ligands are denuded by the beta-ligand transferase activity of CblC to the common cob(II)alamin intermediate.	5,6-dimethylbenzimidazole	61-82	metabolism of cobalamin associated B	Homo sapiens	112-115
11946578-0	1972	Biosynthesis of 5, 6-dimethylbenzimidazole from riboflavin Transformation of C-1" of riboflavin into C-2 of 5, 6-dimethylbenzimidazole.	5,6-dimethylbenzimidazole	16-42	heterogeneous nuclear ribonucleoprotein C	Homo sapiens	77-80
3528859-9	1986	When P. freudenreichii was cultivated in the presence of o-phenylenediamine and 5,6-dimethylbenzimidazole, which may be considered precursors as well as antimetabolites of vitamin B12, the stimulation of biosynthesis of substances with biological activity of vitamin B12 took place.	5,6-dimethylbenzimidazole	80-105	NADH:ubiquinone oxidoreductase subunit B3	Homo sapiens	180-183
3528859-9	1986	When P. freudenreichii was cultivated in the presence of o-phenylenediamine and 5,6-dimethylbenzimidazole, which may be considered precursors as well as antimetabolites of vitamin B12, the stimulation of biosynthesis of substances with biological activity of vitamin B12 took place.	5,6-dimethylbenzimidazole	80-105	NADH:ubiquinone oxidoreductase subunit B3	Homo sapiens	267-270
5808503-0	1969	The biosynthesis of the 5,6-dimethylbenzimidazole moiety of vitamin B12.	5,6-dimethylbenzimidazole	24-49	NADH:ubiquinone oxidoreductase subunit B3	Homo sapiens	68-71
5645435-0	1968	Biosynthesis of the 5,6-dimethylbenzimidazole moiety of vitamin B12.	5,6-dimethylbenzimidazole	20-45	NADH:ubiquinone oxidoreductase subunit B3	Homo sapiens	64-67
11946578-0	1972	Biosynthesis of 5, 6-dimethylbenzimidazole from riboflavin Transformation of C-1" of riboflavin into C-2 of 5, 6-dimethylbenzimidazole.	5,6-dimethylbenzimidazole	16-42	complement C2	Homo sapiens	101-104
11946578-0	1972	Biosynthesis of 5, 6-dimethylbenzimidazole from riboflavin Transformation of C-1" of riboflavin into C-2 of 5, 6-dimethylbenzimidazole.	5,6-dimethylbenzimidazole	108-134	heterogeneous nuclear ribonucleoprotein C	Homo sapiens	77-80
11946578-0	1972	Biosynthesis of 5, 6-dimethylbenzimidazole from riboflavin Transformation of C-1" of riboflavin into C-2 of 5, 6-dimethylbenzimidazole.	5,6-dimethylbenzimidazole	108-134	complement C2	Homo sapiens	101-104
31341578-4	2019	Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52-1.30 muM and 0.56-1.51 muM against four human tumor cell lines investigated.	5,6-dimethylbenzimidazole	75-101	latexin	Homo sapiens	176-179
29387363-3	2018	The effect of cobalt and the lower ligand 5,6-dimethylbenzimidazole (DMBI) or its natural precursors (riboflavin and nicotinamide) on active B12 production was evaluated.	5,6-dimethylbenzimidazole	42-67	NADH:ubiquinone oxidoreductase subunit B3	Homo sapiens	141-144
29387363-3	2018	The effect of cobalt and the lower ligand 5,6-dimethylbenzimidazole (DMBI) or its natural precursors (riboflavin and nicotinamide) on active B12 production was evaluated.	5,6-dimethylbenzimidazole	69-73	NADH:ubiquinone oxidoreductase subunit B3	Homo sapiens	141-144
29387363-5	2018	A B12 content of 12-37 mug kg-1 was produced in BM; this content increased 10-fold with cobalt and reached 940-1,480 mug kg-1 with both cobalt and DMBI.	5,6-dimethylbenzimidazole	147-151	NADH:ubiquinone oxidoreductase subunit B3	Homo sapiens	2-5