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Compound Detail

CHEMBL191881

LEUPEPTIN
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CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCNC(=N)N
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL191881
Name LEUPEPTIN
Phase Preclinical
Structure Type BOTH
InChI Key GDBQQVLCIARPGH-ULQDDVLXSA-N
25
Targets
42
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

426.6
MW (Da)
0.02
ALogP
5
HBA
6
HBD
166.3
PSA (Ų)
0.10
QED
1
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H38N6O4
MW 426.56
Aromatic Rings 0
Heavy Atoms 30
NP-Likeness 0.53

Activity Summary

IC50 28 meas. best 8.66
Ki 14 meas. best 10.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin B
CHEMBL3232689
 Ki 10.7 9.3 0.0 2
Papain
CHEMBL4779
 IC50 8.66 8.66 2.2 1
Procathepsin L
CHEMBL3837
 IC50 8.6 8.39 2.5 2
Cathepsin B
CHEMBL4072
 Ki 8.3 8.2 5.0 3
Falcipain 2
CHEMBL5800
 IC50 8.24 7.4367 5.8 3
Cathepsin B
CHEMBL4072
 IC50 8.03 7.43 9.4 3
Cysteine protease
CHEMBL4751
 IC50 8.0 8.0 10.0 1
Cathepsin K
CHEMBL268
 Ki 7.62 7.62 24.0 1
Serine protease hepsin
CHEMBL2079849
 Ki 7.21 7.21 61.0 1
Unchecked
CHEMBL612545
 IC50 7.15 6.965 70.3 2
Calpain-1 catalytic subunit
CHEMBL4062
 IC50 7.1 7.1 80.0 1
Cysteine protease falcipain-3
CHEMBL1697661
 IC50 7.06 7.035 87.0 2
Hepatocyte growth factor activator
CHEMBL3351190
 Ki 6.73 6.73 188.0 1
Calpain-1 catalytic subunit
CHEMBL3891
 IC50 6.52 6.52 300.0 1
Cathepsin B
CHEMBL2323
 IC50 6.51 6.51 310.0 1
Trypsin
CHEMBL2366
 IC50 6.3 6.3 500.0 1
Trypsin
CHEMBL2095204
 IC50 6.22 6.22 600.0 1
Suppressor of tumorigenicity 14 protein
CHEMBL3018
 Ki 6.16 5.94 696.0 2
Plasminogen
CHEMBL1801
 IC50 5.92 5.92 1200.0 1
Transmembrane protease serine 6
CHEMBL1795139
 Ki 5.62 5.505 2400.0 2
Plasminogen
CHEMBL2957
 IC50 5.43 5.43 3700.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.2 4.6933 6260.0 3
Serine protease 1
CHEMBL3769
 IC50 5.09 5.09 8100.0 1
Pro-cathepsin H
CHEMBL2225
 Ki 5.04 5.04 9200.0 2
Prothrombin
CHEMBL4471
 IC50 4.92 4.92 12000.0 1
Plasma kallikrein
CHEMBL2000
 IC50 4.4 4.4 40000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.125 hr -
T1/2 0.01667 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin B Ki = 0.02 nM 10.7 Competitive inhibition of goat brain cathepsin B 24642566
Papain IC50 = 2.2 nM 8.66 Inhibition of papaya papain using cbzFRamc substrate preincubated for 10 mins fo... 32998509
Procathepsin L IC50 = 2.5 nM 8.6 Compound was measured for inhibition of collagenolytic of human Cathepsin L 9784105
Cathepsin B Ki = 5.0 nM 8.3 Inhibition of human liver cathepsin B 23623677
Falcipain 2 IC50 = 5.8 nM 8.24 Inhibitory concentration against recombinant Falcipain-2 15887974
Procathepsin L IC50 = 6.6 nM 8.18 Inhibition of human cathepsin L. 9784105
Cathepsin B Ki = 7.0 nM 8.15 Inhibition of human liver cathepsin B 24913985
Cathepsin B Ki = 7.0 nM 8.15 Inhibition of human liver cathepsin B 24642566
Cathepsin B IC50 = 9.4 nM 8.03 Inhibition of human cathepsin B 9784105
Cysteine protease IC50 = 10.0 nM 8.0 Inhibition of Leishmania donovani cysteine protease 16509575
Cathepsin B Ki = 12.5 nM 7.9 Competitive inhibition of goat brain cathepsin B 24913985
Cathepsin K Ki = 24.0 nM 7.62 Competitive inhibition of recombinant human cathepsin K expressed in Pichia past... 28228366
Cathepsin B IC50 = 47.0 nM 7.33 Inhibition of cathepsin B by spectrofluorimetry 18995931
Serine protease hepsin Ki = 61.0 nM 7.21 Inhibition of recombinant hepsin (unknown origin) using Boc-QAR-AMC as substrate... 25408834
Unchecked IC50 = 70.3 nM 7.15 Compound was tested for its inhibitory activity against cathepsin L -
Calpain-1 catalytic subunit IC50 = 80.0 nM 7.1 Inhibitory activity against porcine calpain I using Suc-Leu-Tyr-AMC fluorogenic ... 16185867
Falcipain 2 IC50 = 87.0 nM 7.06 Inhibition of Cysteine protease falcipain-2 in Plasmodium falciparum HB3 infecte... 18443109
Cysteine protease falcipain-3 IC50 = 87.0 nM 7.06 Inhibition of Cysteine protease falcipain-3 in Plasmodium falciparum HB3 infecte... 18443109
Falcipain 2 IC50 = 98.0 nM 7.01 Inhibition of Cysteine protease falcipain-2 in Plasmodium falciparum HB3-leuR1 m... 18443109
Cysteine protease falcipain-3 IC50 = 98.0 nM 7.01 Inhibition of Cysteine protease falcipain-3 in Plasmodium falciparum HB3-leuR1 m... 18443109

Literature References

PubMed DOI Target Context # Activities
10617079 10.1016/s0960-894x(99)00618-6 Cathepsin B 11
18443109 10.1128/aac.00057-08 Plasmodium falciparum 9
24642566 10.1016/j.ejmech.2014.03.007 Cathepsin B 6
18443109 10.1128/aac.00057-08 Unchecked 5
18443109 10.1128/aac.00057-08 Falcipain 2 4
18443109 10.1128/aac.00057-08 Cysteine protease falcipain-3 4
24642566 10.1016/j.ejmech.2014.03.007 Cathepsin H 3
24913985 10.1016/j.bmc.2014.05.037 Cathepsin B 3
25408834 10.1021/ml500254r Unchecked 2
25069058 10.1021/np500106w Trypsin 2
32998509 10.1021/acs.jnatprod.0c00201 Papain 2
31658420 10.1021/acs.jmedchem.9b01060 No relevant target 2
32998509 10.1021/acs.jnatprod.0c00201 Unchecked 2
9784105 10.1021/jm9803065 Procathepsin L 2
- 10.1016/0960-894X(95)00236-M Cathepsin B 2
20684597 10.1021/jm100183e Transmembrane protease serine 6 2
17921140 10.1074/jbc.m705646200 Unchecked 2
33002682 10.1016/j.bmc.2020.115756 Unchecked 1
8478905 10.1021/jm00060a016 Prothrombin 1
- 10.1016/0960-894X(95)00236-M Unchecked 1

Data from ChEMBL 36 via Core Engine