Inhibitors | Comment | Organism | Structure |
---|---|---|---|
(10S,13S)-10-(1H-indol-3-ylmethyl)-8,11-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-9,12-diazabicyclo[13.2.2]nonadeca-1(17),15,18-triene-13-carboxamide | - |
synthetic construct | |
(12S,15S)-12-(1H-indol-3-ylmethyl)-10,13-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-11,14-diazabicyclo[15.2.2]henicosa-1(19),17,20-triene-15-carboxamide | - |
synthetic construct | |
(9S,12S)-9-(1H-indol-3-ylmethyl)-7,10-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-8,11-diazabicyclo[12.2.2]octadeca-1(16),14,17-triene-12-carboxamide | - |
synthetic construct | |
L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
additional information | peptide inhibitors that incorporate 3-oxotetrahydrofuran and 3-oxotetrahydrothiophene 1,1-dioxide groups have the highest activities. For cyclopentanone-based inhibitors, incorporation of electron-withdrawing groups such as O and SO2 into the ring improves their activities. Alkylamino substituents, with an optimal spacer length of 6 carbon atoms, can be added to the inhibitors to bind in the S1 subsite. Incorporating conformationally constrained peptide segments into the inhibitors do not improve their activities | synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1-glycyl-4-oxopyrrolidin-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclohexyl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclopentyl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobenzyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobutyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-tryptophanamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(5-aminopentyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(7-aminoheptyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct | |
N-[(benzyloxy)carbonyl]-L-tryptophyl-N-[(trans-4-aminocyclohexyl)methyl]-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | - |
synthetic construct |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
synthetic construct | - |
- |
- |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
D-Val-Leu-Lys-p-nitroanilide + H2O | - |
synthetic construct | D-Val-Leu-Lys + p-nitroaniline | - |
? |
IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
---|---|---|---|---|---|
0.0057 | - |
one of the most effective inhibitors | synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide | |
0.009 | - |
one of the most effective inhibitors | synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(6-aminohexyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
0.013 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1,1-dioxido-4-oxotetrahydrothiophen-3-yl)-L-phenylalaninamide | |
0.019 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobenzyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
0.022 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
0.025 | - |
- |
synthetic construct | (12S,15S)-12-(1H-indol-3-ylmethyl)-10,13-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-11,14-diazabicyclo[15.2.2]henicosa-1(19),17,20-triene-15-carboxamide | |
0.03 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-tryptophanamide | |
0.051 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(7-aminoheptyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
0.054 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-[(trans-4-aminocyclohexyl)methyl]-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
0.062 | - |
- |
synthetic construct | (10S,13S)-10-(1H-indol-3-ylmethyl)-8,11-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-9,12-diazabicyclo[13.2.2]nonadeca-1(17),15,18-triene-13-carboxamide | |
0.1 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(5-aminopentyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
0.14 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(4-aminobutyl)-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
0.3 | - |
- |
synthetic construct | (9S,12S)-9-(1H-indol-3-ylmethyl)-7,10-dioxo-N-(4-oxotetrahydrofuran-3-yl)-2-oxa-8,11-diazabicyclo[12.2.2]octadeca-1(16),14,17-triene-12-carboxamide | |
0.35 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(1-glycyl-4-oxopyrrolidin-3-yl)-L-phenylalaninamide | |
0.375 | - |
- |
synthetic construct | L-tryptophyl-N-(4-oxotetrahydrofuran-3-yl)-L-phenylalaninamide | |
1 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclopentyl)-L-phenylalaninamide | |
1 | - |
- |
synthetic construct | N-[(benzyloxy)carbonyl]-L-tryptophyl-N-(2-oxocyclohexyl)-L-phenylalaninamide |