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Literature summary 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.
    View publication on PubMed

Cloned(Commentary)

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

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.1.1.6
-
 Rattus norvegicus

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.1.1.6 (2E)-4,7-anhydro-1,2,3-trideoxy-1-(2,3-dihydroxy-5-nitrobenzamido)-L-ribo-hept-2-enitol
-
 Rattus norvegicus
2.1.1.6 1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]-4-(trifluoromethyl)-1H-imidazole
-
 Rattus norvegicus
2.1.1.6 1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]benzo[d]imidazole
-
 Rattus norvegicus
2.1.1.6 1-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]pyridin-4(1H)-one
-
 Rattus norvegicus
2.1.1.6 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
2.1.1.6 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
2.1.1.6 6-methyl-9-[(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-beta-D-ribo-hept-5-enofuranosyl]purine
-
 Rattus norvegicus
2.1.1.6 9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]purine
-
 Rattus norvegicus
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 N6-methyl-9-[(5E)-5,6,7-trideoxy-7-(2,3-dihydroxy-5-nitrobenzamido)-beta-D-ribo-hept-5-enofuranosyl]adenine
-
 Rattus norvegicus
2.1.1.6 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

EC Number Organism UniProt Comment Textmining
2.1.1.6 Rattus norvegicus
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.1.1.6
-
 Rattus norvegicus

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.1.1.6 liver
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

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

Synonyms

EC Number Synonyms Comment Organism
2.1.1.6 catechol-O-methyltransferase
-
 Rattus norvegicus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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
2.1.1.6 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