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Literature summary for 3.4.22.34 extracted from

  • Lee, J.; Bogyo, M.
    Synthesis and evaluation of aza-peptidyl inhibitors of the lysosomal asparaginyl endopeptidase, legumain (2011), Bioorg. Med. Chem. Lett., 22, 1340-1343.
    View publication on PubMedView publication on EuropePMC

Inhibitors

Inhibitors Comment Organism Structure
(1-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]cyclopropyl)carbamic acid
-
Homo sapiens
(1-[[(2S)-2-[[2-(2-amino-2-oxoethyl)-2-[[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]carbonyl]hydrazinyl]carbonyl]pyrrolidin-1-yl]carbonyl]cyclopropyl)carbamic acid
-
Homo sapiens
(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidine-1-carboxylic acid
-
Homo sapiens
(2S)-2-[[2-(2-amino-2-oxoethyl)-2-[[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]carbonyl]hydrazinyl]carbonyl]pyrrolidine-1-carboxylic acid
-
Homo sapiens
(3-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]phenyl)carbamic acid
-
Homo sapiens
(4-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]benzyl)carbamic acid
-
Homo sapiens
2-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]piperidine-1-carboxylic acid
-
Homo sapiens
3-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]-3,4-dihydroisoquinoline-2(1H)-carboxylic acid
-
Homo sapiens
4-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]-1,3-thiazolidine-3-carboxylic acid
-
Homo sapiens
ethyl (2E)-4-[1-(2-amino-2-oxoethyl)-2-[[(2S)-1-(2-oxopropanoyl)pyrrolidin-2-yl]carbonyl]hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[(2E)-2-(acetylamino)but-2-enoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[(2R)-2-(acetylamino)-3-(4-hydroxy-3-nitrophenyl)propanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[(2R)-2-(acetylamino)butanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[(2R)-2-(acetylamino)pent-4-ynoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[2-(acetylamino)-2-methylpropanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[2-(acetylamino)-3-methylbut-2-enoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[3-(acetylamino)benzoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-([(2S)-1-[4-(acetylamino)benzoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-[[(2S)-1-[[(2R)-1-acetylpiperidin-2-yl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-[[(2S)-1-[[(3S)-2-acetyl-1,2,3,4-tetrahydroisoquinolin-3-yl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-[[(2S)-1-[[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2E)-4-[2-[[(2S)-1-[[1-(acetylamino)cyclopropyl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
-
Mus musculus
ethyl (2S,3S)-3-[[1-(2-amino-2-oxoethyl)-2-[([2S)-1-(2-oxopropanoyl)pyrrolidin-2-yl]carbonyl]hydrazinyl]carbonyl]oxirane-2-carboxylate
-
Mus musculus
ethyl (2S,3S)-3-[[2-([(2S)-1-[(2R)-2-(acetylamino)butanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]carbonyl]oxirane-2-carboxylate
-
Mus musculus
ethyl (2S,3S)-3-[[2-([(2S)-1-[(2R)-2-(acetylamino)pent-4-ynoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]carbonyl]oxirane-2-carboxylate
-
Mus musculus
ethyl (2S,3S)-3-[[2-[[(2S)-1-[[1-(acetylamino)cyclopropyl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]carbonyl]oxirane-2-carboxylate
-
Mus musculus
[(2S)-1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-3-[4-hydroxy-3-[hydroxy(oxo)ammonio]phenyl]-1-oxopropan-2-yl]carbamate
-
Homo sapiens
[(2Z)-1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-1-oxobut-2-en-2-yl]carbamic acid
-
Homo sapiens
[1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-1-oxobutan-2-yl]carbamic acid
-
Homo sapiens
[1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-1-oxopent-4-yn-2-yl]carbamic acid
-
Homo sapiens
[1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]carbamic acid
-
Homo sapiens
[1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-3-methyl-1-oxobut-2-en-2-yl]carbamic acid
-
Homo sapiens
[1-[(2S)-2-[[2-(2-amino-2-oxoethyl)-2-[[(2R,3R)-3-(ethoxycarbonyl)oxiran-2-yl]carbonyl]hydrazinyl]carbonyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]carbamic acid
-
Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
lysosome
-
Mus musculus 5764
-

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Mus musculus
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Cbz-Ala-Ala-Asn-7-amido-4-methylcoumarin + H2O
-
Mus musculus Cbz-Ala-Ala-Asn + 7-amino-4-methylcoumarin
-
?
Cbz-Ala-Ala-Asn-7-amido-4-methylcoumarin + H2O
-
Homo sapiens Cbz-Ala-Ala-Asn + 7-amino-4-methylcoumarin
-
?

Synonyms

Synonyms Comment Organism
AEP
-
Mus musculus
asparaginly endopeptidase
-
Mus musculus
legumain
-
Homo sapiens
lysosomal asparaginyl endopeptidase
-
Mus musculus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000044
-
pH 5.8, temperature not specified in the publication Homo sapiens (1-[[(2S)-2-[[2-(2-amino-2-oxoethyl)-2-[[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]carbonyl]hydrazinyl]carbonyl]pyrrolidin-1-yl]carbonyl]cyclopropyl)carbamic acid
0.0000065
-
pH 5.8, temperature not specified in the publication Homo sapiens [1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-1-oxobutan-2-yl]carbamic acid
0.0000065
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[(2R)-2-(acetylamino)butanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.0000081
-
pH 5.8, temperature not specified in the publication Homo sapiens [1-[(2S)-2-[[2-(2-amino-2-oxoethyl)-2-[[(2R,3R)-3-(ethoxycarbonyl)oxiran-2-yl]carbonyl]hydrazinyl]carbonyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]carbamic acid
0.0000083
-
pH 5.8, temperature not specified in the publication Homo sapiens (2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidine-1-carboxylic acid
0.0000086
-
pH 5.8, temperature not specified in the publication Homo sapiens (1-[[(2S)-2-[[2-(2-amino-2-oxoethyl)-2-[[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]carbonyl]hydrazinyl]carbonyl]pyrrolidin-1-yl]carbonyl]cyclopropyl)carbamic acid
0.0000093
-
pH 5.8, temperature not specified in the publication Homo sapiens (1-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]cyclopropyl)carbamic acid
0.0000093
-
pH 5.8, temperature not specified in the publication Homo sapiens (2S)-2-[[2-(2-amino-2-oxoethyl)-2-[[(2S,3S)-3-(ethoxycarbonyl)oxiran-2-yl]carbonyl]hydrazinyl]carbonyl]pyrrolidine-1-carboxylic acid
0.0000093
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-[[(2S)-1-[[1-(acetylamino)cyclopropyl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.000017
-
pH 5.8, temperature not specified in the publication Homo sapiens [1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-1-oxopent-4-yn-2-yl]carbamic acid
0.000017
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[(2R)-2-(acetylamino)pent-4-ynoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.000141
-
pH 5.8, temperature not specified in the publication Homo sapiens [(2Z)-1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-1-oxobut-2-en-2-yl]carbamic acid
0.000141
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[(2E)-2-(acetylamino)but-2-enoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.000148
-
pH 5.8, temperature not specified in the publication Homo sapiens [1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-3-methyl-1-oxobut-2-en-2-yl]carbamic acid
0.000148
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[2-(acetylamino)-3-methylbut-2-enoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.000167
-
pH 5.8, temperature not specified in the publication Homo sapiens 4-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]-1,3-thiazolidine-3-carboxylic acid
0.000167
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-[[(2S)-1-[[(4S)-3-acetyl-1,3-thiazolidin-4-yl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.000198
-
pH 5.8, temperature not specified in the publication Homo sapiens [1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]carbamic acid
0.000198
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[2-(acetylamino)-2-methylpropanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.000267
-
pH 5.8, temperature not specified in the publication Homo sapiens (4-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]benzyl)carbamic acid
0.000267
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[4-(acetylamino)benzoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.000638
-
pH 5.8, temperature not specified in the publication Homo sapiens 2-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]piperidine-1-carboxylic acid
0.000638
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-[[(2S)-1-[[(2R)-1-acetylpiperidin-2-yl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.001
-
pH 5.8, temperature not specified in the publication Homo sapiens (3-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]phenyl)carbamic acid
0.001
-
pH 5.8, temperature not specified in the publication Homo sapiens 3-[[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]carbonyl]-3,4-dihydroisoquinoline-2(1H)-carboxylic acid
0.001
-
pH 5.8, temperature not specified in the publication Homo sapiens [(2S)-1-[(2S)-2-([2-(2-amino-2-oxoethyl)-2-[(2E)-4-ethoxy-4-oxobut-2-enoyl]hydrazinyl]carbonyl)pyrrolidin-1-yl]-3-[4-hydroxy-3-[hydroxy(oxo)ammonio]phenyl]-1-oxopropan-2-yl]carbamate
0.001
-
IC50 above 0.001 mM, in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[3-(acetylamino)benzoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.001
-
IC50 above 0.001 mM, in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-[[(2S)-1-[[(3S)-2-acetyl-1,2,3,4-tetrahydroisoquinolin-3-yl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.001
-
IC50 above 0.001 mM, in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[2-([(2S)-1-[(2R)-2-(acetylamino)-3-(4-hydroxy-3-nitrophenyl)propanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]-4-oxobut-2-enoate
0.0044
-
IC50 above 0.001 mM, in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2S,3S)-3-[[2-[[(2S)-1-[[1-(acetylamino)cyclopropyl]carbonyl]pyrrolidin-2-yl]carbonyl]-1-(2-amino-2-oxoethyl)hydrazinyl]carbonyl]oxirane-2-carboxylate
0.0081
-
IC50 above 0.001 mM, in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2S,3S)-3-[[2-([(2S)-1-[(2R)-2-(acetylamino)butanoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]carbonyl]oxirane-2-carboxylate
0.0083
-
in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2E)-4-[1-(2-amino-2-oxoethyl)-2-[[(2S)-1-(2-oxopropanoyl)pyrrolidin-2-yl]carbonyl]hydrazinyl]-4-oxobut-2-enoate
0.0086
-
IC50 above 0.001 mM, in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2S,3S)-3-[[2-([(2S)-1-[(2R)-2-(acetylamino)pent-4-ynoyl]pyrrolidin-2-yl]carbonyl)-1-(2-amino-2-oxoethyl)hydrazinyl]carbonyl]oxirane-2-carboxylate
0.0093
-
IC50 above 0.001 mM, in 0.1 M citrate-phosphate, 4 mM dithiothreitol, pH 5.8, at 25°C Mus musculus ethyl (2S,3S)-3-[[1-(2-amino-2-oxoethyl)-2-[([2S)-1-(2-oxopropanoyl)pyrrolidin-2-yl]carbonyl]hydrazinyl]carbonyl]oxirane-2-carboxylate