Literature summary for 2.1.1.6 extracted from

Ellermann, M.; Paulini, R.; Jakob-Roetne, R.; Lerner, C.; Borroni, E.; Roth, D.; Ehler, A.; Schweizer, W.B.; Schlatter, D.; Rudolph, M.G.; Diederich, F.
Molecular recognition at the active site of catechol-O-methyltransferase (COMT): adenine replacements in bisubstrate inhibitors (2011), Chemistry, 17, 6369-6381.

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Cloned(Commentary)

Cloned (Comment)	Organism
soluble part from M44 to S264 expressed in Escherichia coli W3110[pREP4]	Rattus norvegicus

Crystallization (Commentary)

Crystallization (Comment)	Organism
-	Rattus norvegicus

Inhibitors

Inhibitors	Comment	Organism	Structure
(2E)-4,7-anhydro-1,2,3-trideoxy-1-(2,3-dihydroxy-5-nitrobenzamido)-L-ribo-hept-2-enitol	-	Rattus norvegicus
1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-4-(trifluoromethyl)-1H-imidazole	-	Rattus norvegicus
1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]benzo[d]imidazole	-	Rattus norvegicus
1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]pyridin-4(1H)-one	-	Rattus norvegicus
5-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-5H-imidazo[4,5-c]pyridine	-	Rattus norvegicus
5-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-5H-pyrrolo[3,2-c]pyridine	-	Rattus norvegicus
6-methyl-9-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]purine	-	Rattus norvegicus
9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]purine	-	Rattus norvegicus
N-ethyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-imidazole-4-carboxamide	-	Rattus norvegicus
N-methyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-1,2,4-triazole-3-carboxamide	-	Rattus norvegicus
N-methyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-imidazole-4-carboxamide	-	Rattus norvegicus
N-[(2E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-en-1-yl]-2,3-dihydroxy-5-nitrobenzamide	-	Rattus norvegicus
N-[(2E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-en-1-yl]-4'-fluoro-4,5-dihydroxybiphenyl-3-carboxamide	-	Rattus norvegicus
N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]adenine	-	Rattus norvegicus
pyridin-4-yl (5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-1-thio-beta-D-ribo-hept-5-enofuranoside	-	Rattus norvegicus

Organism

Organism	UniProt	Comment	Textmining
Rattus norvegicus	-	-	-

Purification (Commentary)

Purification (Comment)	Organism
-	Rattus norvegicus

Source Tissue

Source Tissue	Comment	Organism	Textmining
liver	-	Rattus norvegicus	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
benzene-1,2-diol + S-adenosyl-L-methionine	-	Rattus norvegicus	? + S-adenosyl-L-homocysteine	-	?
L-dopa + S-adenosyl-L-methionine	-	Rattus norvegicus	? + S-adenosyl-L-homocysteine	-	?

Synonyms

Synonyms	Comment	Organism
catechol-O-methyltransferase	-	Rattus norvegicus

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
0.000001	-	6-methyl-9-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]purine	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.000002	-	N-[(2E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-en-1-yl]-2,3-dihydroxy-5-nitrobenzamide	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.000007	-	N-[(2E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-en-1-yl]-4'-fluoro-4,5-dihydroxybiphenyl-3-carboxamide	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.000007	-	N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]adenine	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.000034	-	9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]purine	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.000132	-	pyridin-4-yl (5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-1-thio-beta-D-ribo-hept-5-enofuranoside	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.002378	-	5-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-5H-pyrrolo[3,2-c]pyridine	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.0024	-	5-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-5H-imidazo[4,5-c]pyridine	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.004645	-	1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-4-(trifluoromethyl)-1H-imidazole	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.007022	-	(2E)-4,7-anhydro-1,2,3-trideoxy-1-(2,3-dihydroxy-5-nitrobenzamido)-L-ribo-hept-2-enitol	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.0104	-	N-ethyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-imidazole-4-carboxamide	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.014	-	1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]benzo[d]imidazole	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.0156	-	N-methyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-1,2,4-triazole-3-carboxamide	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.0199	-	N-methyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-imidazole-4-carboxamide	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus
0.0749	-	1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]pyridin-4(1H)-one	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
0.000006	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	6-methyl-9-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]purine
0.000009	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	N-[(2E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-en-1-yl]-2,3-dihydroxy-5-nitrobenzamide
0.000031	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	N-[(2E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-en-1-yl]-4'-fluoro-4,5-dihydroxybiphenyl-3-carboxamide
0.000032	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]adenine
0.000155	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]purine
0.000596	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	pyridin-4-yl (5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-1-thio-beta-D-ribo-hept-5-enofuranoside
0.0107	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	5-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-5H-pyrrolo[3,2-c]pyridine
0.0108	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	5-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-5H-imidazo[4,5-c]pyridine
0.0209	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-4-(trifluoromethyl)-1H-imidazole
0.0316	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	(2E)-4,7-anhydro-1,2,3-trideoxy-1-(2,3-dihydroxy-5-nitrobenzamido)-L-ribo-hept-2-enitol
0.0468	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	N-ethyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-imidazole-4-carboxamide
0.0628	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]benzo[d]imidazole
0.0703	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	N-methyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-1,2,4-triazole-3-carboxamide
0.0895	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	N-methyl-1-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]-1H-imidazole-4-carboxamide
0.336	-	liver homogenate, substrate benzene-1,2-diol, pH 7.6, 37°C	Rattus norvegicus	1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]pyridin-4(1H)-one

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Release 2023.1 (January 2023)