Any feedback?
Literature summary for 3.4.24.86 extracted from
- Discovery of novel hydroxamates as highly potent tumor necrosis factor-alpha converting enzyme inhibitors: Part I--discovery of two binding modes (2008), J. Med. Chem., 51, 725-736.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| the catalytic domain of recombinant human TNF-converting enzyme (residues 215-477 with two mutations S266A and N452Q) and a His-tagged tail is purified from the baculovirus/Hi5 cells expression system using affinity chromatography | Homo sapiens |
Crystallization (Commentary)
| Crystallization (Comment) | Organism |
|---|---|
| TACE mutant V353G is crystallized with the respective inhibitors with a resolution of 1.7 A using the hanging drop method | Homo sapiens |
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| S266A/N452Q | the catalytic domain of recombinant human TNF-converting enzyme (residues 215-477) with two mutations S266A and N452Q is used | Homo sapiens |
| V353G | TACE mutant V353G is crystallized with the respective inhibitors with a resolution of 1.7 A using the hanging drop method | Homo sapiens |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (1R,2R)-2-(3-phenoxylphenyl)-2-trans-carbomethoxylcyclopropane hydroxamic acid | - |
Homo sapiens |  |
| (1R,2R)-2-trans-carboisopropoxyl-2-[3-(2-methylquinolin-4-yl)methoxylphenyl]cyclopropane hydroxyamic acid | - |
Homo sapiens | |
| (1R,2R)-2-trans-N-benzylaminocarbonyl-2-[3-(2-methylquinolin-4-yl)methoxylphenyl]cyclopropane hydroxyamic acid | - |
Homo sapiens | |
| (1R,2R)-2-[3-(3,4-dichlorobenzyloxy)phenyl]-2-trans-carbomethoxylcyclopropane hydroxamic acid | - |
Homo sapiens | |
| (1R,2R)-N-hydroxy-2-[(4-methylpiperazin-1-yl)carbonyl]-2-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropanecarboxamide | - |
Homo sapiens | |
| (1R,2R)-N1-benzyl-N2-hydroxy-N1-methyl-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2R)-N1-cyclohexyl-N2-hydroxy-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2R)-N2-hydroxy-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]-N1-phenylcyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2R)-N2-hydroxy-N1,N1-dimethyl-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2R)-N2-hydroxy-N1-methyl-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2S)-1-[4-(benzyloxy)benzyl]-N2-hydroxycyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2S)-1-[4-(but-2-yn-1-yloxy)benzyl]-N2-hydroxycyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2S)-N2-hydroxy-1-[4-[(2-methylquinolin-4-yl)methoxy]benzyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2S)-N2-hydroxy-N1,N1-dimethyl-1-[4-[(2-methylquinolin-4-yl)methoxy]benzyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1R,2S)-N2-hydroxy-N1-methyl-1-[4-[(2-methylquinolin-4-yl)methoxy]benzyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| (1S,2R)-N-hydroxy-2-{4-[(2-imino-1,2-dihydroquinolin-4-yl)methoxy]benzyl}-2-(methoxycarbonyl)cyclopropanecarboximidic acid | - |
Homo sapiens | |
| 1-methylethyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 2-(3-benzyloxyphenyl)-2-trans-carbomethoxylcyclopropane hydroxyamic acid | - |
Homo sapiens | |
| 2-[3-(2-methylquinolin-4-yl)methoxylphenyl]-2-trans-carboxamidocyclopropane hydroxyamic acid | - |
Homo sapiens | |
| 2-[3-(2-methylquinolin-4-yl)methoxyphenyl]-2-trans-carbomethoxylcyclopropane hydroxyamic acid | - |
Homo sapiens | |
| ethyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| ethyl (1R,2S)-2-(hydroxycarbamoyl)-1-(4-phenoxybenzyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-1-[3-(2-[3-[(1Z)-buta-1,3-dien-1-yl]phenyl]ethoxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-1-[3-(benzyloxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-1-[3-(but-2-yn-1-yloxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-1-[3-(cyclohexylmethoxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-1-[3-[(4-chlorobenzyl)oxy]phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-(3-methoxyphenyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-(3-[[3-(trifluoromethyl)benzyl]oxy]phenyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-(3-[[4-(trifluoromethyl)benzyl]oxy]phenyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(2-methylphenoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(2-naphthalen-2-ylethoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(2-phenylethoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(4-methylphenoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(naphthalen-2-ylmethoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(naphthalen-2-yloxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-[(3-methoxybenzyl)oxy]phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2S)-1-[4-(benzyloxy)benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2S)-1-[4-(but-2-yn-1-yloxy)benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2S)-1-[4-(cyclohexylmethoxy)benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2S)-1-[4-[(2-chlorobenzyl)oxy]benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2S)-1-[4-[(3,4-dichlorobenzyl)oxy]benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2S)-2-(hydroxycarbamoyl)-1-[4-(2-naphthalen-1-ylethoxy)benzyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| methyl (1R,2S)-2-(hydroxycarbamoyl)-1-[4-(2-naphthalen-2-ylethoxy)benzyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| N-[(4S,5S,7R)-2-[7-(1-benzylpiperidin-4-yl)]methylcarbamoyl-5-hydroxy-2-methyloct-4-yl]-N'-[(R)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]isophthalamide | - |
Homo sapiens | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | - |
- |
- |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 7-methoxycoumarin-4-(yl)acetyl-Pro-Leu-Ala-Gln-Ala-Val-Arg-Ser-Ser-Ser-N-3-(2,4-dinitrophenyl)-L-2,3-diaminopropionyl-Arg-NH2 + H2O | an internally quenched peptide substrate is used | Homo sapiens | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| TACE | - |
Homo sapiens |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 7.5 | - |
assay at | Homo sapiens |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.000001 | - |
(1R,2S)-N2-hydroxy-N1,N1-dimethyl-1-[4-[(2-methylquinolin-4-yl)methoxy]benzyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.000003 | - |
(1R,2S)-N2-hydroxy-1-[4-[(2-methylquinolin-4-yl)methoxy]benzyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.000005 | - |
1-methylethyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.000008 | - |
2-[3-(2-methylquinolin-4-yl)methoxyphenyl]-2-trans-carbomethoxylcyclopropane hydroxyamic acid | - |
Homo sapiens | |
| 0.000008 | - |
(1R,2R)-2-trans-carboisopropoxyl-2-[3-(2-methylquinolin-4-yl)methoxylphenyl]cyclopropane hydroxyamic acid | - |
Homo sapiens | |
| 0.000009 | - |
(1R,2R)-N1-cyclohexyl-N2-hydroxy-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.000011 | - |
(1R,2R)-N2-hydroxy-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]-N1-phenylcyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.000011 | - |
(1R,2R)-2-[3-(3,4-dichlorobenzyloxy)phenyl]-2-trans-carbomethoxylcyclopropane hydroxamic acid | - |
Homo sapiens | |
| 0.000012 | - |
(1S,2R)-N-hydroxy-2-{4-[(2-imino-1,2-dihydroquinolin-4-yl)methoxy]benzyl}-2-(methoxycarbonyl)cyclopropanecarboximidic acid | - |
Homo sapiens | |
| 0.000014 | - |
(1R,2S)-N2-hydroxy-N1-methyl-1-[4-[(2-methylquinolin-4-yl)methoxy]benzyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.000016 | - |
ethyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.000018 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-(3-[[4-(trifluoromethyl)benzyl]oxy]phenyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00005 | - |
methyl (1R,2R)-1-[3-(2-[3-[(1Z)-buta-1,3-dien-1-yl]phenyl]ethoxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00005 | - |
methyl (1R,2R)-1-[3-[(4-chlorobenzyl)oxy]phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00006 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(2-naphthalen-2-ylethoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00007 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-(3-[[3-(trifluoromethyl)benzyl]oxy]phenyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00007 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(naphthalen-2-yloxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00008 | - |
(1R,2S)-1-[4-(but-2-yn-1-yloxy)benzyl]-N2-hydroxycyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.00008 | - |
N-[(4S,5S,7R)-2-[7-(1-benzylpiperidin-4-yl)]methylcarbamoyl-5-hydroxy-2-methyloct-4-yl]-N'-[(R)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]isophthalamide | - |
Homo sapiens | |
| 0.0001 | - |
(1R,2R)-N2-hydroxy-N1-methyl-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.00011 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-[(3-methoxybenzyl)oxy]phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00013 | - |
methyl (1R,2S)-1-[4-[(3,4-dichlorobenzyl)oxy]benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00014 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(4-methylphenoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00014 | - |
(1R,2R)-2-trans-N-benzylaminocarbonyl-2-[3-(2-methylquinolin-4-yl)methoxylphenyl]cyclopropane hydroxyamic acid | - |
Homo sapiens | |
| 0.00019 | - |
2-(3-benzyloxyphenyl)-2-trans-carbomethoxylcyclopropane hydroxyamic acid | - |
Homo sapiens | |
| 0.00024 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(2-methylphenoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00026 | - |
methyl (1R,2S)-1-[4-[(2-chlorobenzyl)oxy]benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00029 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(2-phenylethoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.00036 | - |
(1R,2S)-1-[4-(benzyloxy)benzyl]-N2-hydroxycyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.00042 | - |
methyl (1R,2S)-1-[4-(but-2-yn-1-yloxy)benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.0007 | - |
2-[3-(2-methylquinolin-4-yl)methoxylphenyl]-2-trans-carboxamidocyclopropane hydroxyamic acid | - |
Homo sapiens | |
| 0.0008 | - |
methyl (1R,2S)-1-[4-(benzyloxy)benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.0009 | - |
methyl (1R,2R)-1-[3-(cyclohexylmethoxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.0011 | - |
(1R,2R)-2-(3-phenoxylphenyl)-2-trans-carbomethoxylcyclopropane hydroxamic acid | - |
Homo sapiens | |
| 0.0012 | - |
methyl (1R,2R)-1-[3-(benzyloxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.0016 | - |
methyl (1R,2R)-1-[3-(but-2-yn-1-yloxy)phenyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.0027 | - |
(1R,2R)-N2-hydroxy-N1,N1-dimethyl-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.003 | - |
(1R,2R)-N1-benzyl-N2-hydroxy-N1-methyl-1-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropane-1,2-dicarboxamide | - |
Homo sapiens | |
| 0.003 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-(3-methoxyphenyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.003 | - |
methyl (1R,2R)-2-(hydroxycarbamoyl)-1-[3-(naphthalen-2-ylmethoxy)phenyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.0031 | - |
ethyl (1R,2S)-2-(hydroxycarbamoyl)-1-(4-phenoxybenzyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.005 | - |
(1R,2R)-N-hydroxy-2-[(4-methylpiperazin-1-yl)carbonyl]-2-[3-[(2-methylquinolin-4-yl)methoxy]phenyl]cyclopropanecarboxamide | - |
Homo sapiens | |
| 0.026 | - |
methyl (1R,2S)-1-[4-(cyclohexylmethoxy)benzyl]-2-(hydroxycarbamoyl)cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.1 | - |
methyl (1R,2S)-2-(hydroxycarbamoyl)-1-[4-(2-naphthalen-1-ylethoxy)benzyl]cyclopropanecarboxylate | - |
Homo sapiens | |
| 0.1 | - |
methyl (1R,2S)-2-(hydroxycarbamoyl)-1-[4-(2-naphthalen-2-ylethoxy)benzyl]cyclopropanecarboxylate | - |
Homo sapiens | |
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2023.1 (January 2023)
Legal
Curated at
Member of
