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Compound Detail

CHEMBL374508

E-64
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CC(C)C[C@H](NC(=O)[C@H]1O[C@@H]1C(=O)O)C(=O)NCCCCN=C(N)N
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL374508
Name E-64
Phase Preclinical
Structure Type MOL
InChI Key LTLYEAJONXGNFG-DCAQKATOSA-N
18
Targets
85
Activities
4
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

357.4
MW (Da)
-1.46
ALogP
5
HBA
5
HBD
172.4
PSA (Ų)
0.13
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H27N5O5
MW 357.41
Aromatic Rings 0
Heavy Atoms 25
NP-Likeness 0.64

Activity Summary

IC50 70 meas. best 8.7
Ki 13 meas. best 7.6
EC50 1 meas. best 5.54
Kd 1 meas. best 5.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Papain
CHEMBL4779
 IC50 8.7 7.775 2.0 4
Procathepsin L
CHEMBL3837
 IC50 8.64 7.7517 2.3 6
Rhodesain
CHEMBL4188
 IC50 8.51 8.51 3.1 1
Cathepsin K
CHEMBL268
 IC50 8.4 8.4 4.0 1
Cathepsin B
CHEMBL4072
 IC50 8.34 7.968 4.6 5
Cathepsin S
CHEMBL2954
 IC50 8.15 8.15 7.0 1
Unchecked
CHEMBL612545
 IC50 8.05 7.44 9.0 14
Falcipain 2
CHEMBL5800
 IC50 7.82 7.34 15.0 8
Cruzipain
CHEMBL3563
 IC50 7.7 7.05 20.0 2
Unchecked
CHEMBL612545
 Ki 7.6 6.776 25.0 5
Procathepsin L
CHEMBL3837
 Ki 7.52 7.52 30.0 1
Rhodesain
CHEMBL4188
 Ki 7.46 7.46 35.0 1
Cysteine protease falcipain-3
CHEMBL4510
 IC50 7.46 7.29 35.0 2
Calpain-1 catalytic subunit
CHEMBL3891
 IC50 7.0 7.0 100.0 1
Falcipain-3
CHEMBL1250373
 IC50 6.93 6.93 116.2 1
Pro-cathepsin H
CHEMBL2225
 IC50 6.72 6.72 190.0 1
Falcipain 2
CHEMBL5800
 Ki 6.54 5.8233 290.0 3
Cysteine protease falcipain-3
CHEMBL1697661
 IC50 6.32 6.32 481.5 1
Dipeptidyl peptidase 1
CHEMBL2252
 IC50 6.11 6.11 770.0 1
Falcipain 2
CHEMBL5800
 Kd 5.93 5.93 1180.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.71 5.479 1940.0 20
Plasmodium falciparum
CHEMBL364
 EC50 5.54 5.54 2900.0 1
Calpain-1 catalytic subunit
CHEMBL4062
 Ki 5.4 5.4 3960.0 1
Papain
CHEMBL4779
 Ki 5.29 5.29 5080.0 1
Calpain-9
CHEMBL4523126
 IC50 4.94 4.94 11580.0 1
Cathepsin B
CHEMBL4072
 Ki 4.8 4.8 16000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 12.28 10^3/M/s Plasmodium falciparum

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Papain IC50 = 2.0 nM 8.7 Inhibition of papaya papain using Z-Leu-Leu-Arg-AMC as substrate after 30 mins b... 22071522
Procathepsin L IC50 = 2.3 nM 8.64 Inhibition of cathepsin L (unknown origin) using Cbz-Phe-Arg-AMC as substrate pr... 35308030
Rhodesain IC50 = 3.1 nM 8.51 Inhibition of recombinant Trypanosoma brucei rhodesain using Z-FR-AMC as substra... 33992862
Cathepsin K IC50 = 4.0 nM 8.4 Inhibition of human cathepsin K -
Cathepsin B IC50 = 4.6 nM 8.34 Inhibition of cathepsin B (unknown origin) using Cbz-Phe-Arg-AMC as substrate pr... 35308030
Cathepsin B IC50 = 5.0 nM 8.3 Inhibition of human cathepsin B -
Cathepsin S IC50 = 7.0 nM 8.15 Inhibition of human recombinant cathepsin S after 10 mins 17535802
Papain IC50 = 7.0 nM 8.15 Inhibition of papaya papain using Z-Leu-Leu-Arg-AMC as substrate after 30 mins b... 24077527
Unchecked IC50 = 9.0 nM 8.05 Inhibition of Plasmodium chabaudi recombinant chabaupain expressed in Escherichi... 19435664
Cathepsin B IC50 = 10.0 nM 8.0 Inhibition of human recombinant cathepsin B after 10 mins 17535802
Procathepsin L IC50 = 13.0 nM 7.89 Inhibition of human recombinant cathepsin L after 10 mins 17535802
Falcipain 2 IC50 = 15.0 nM 7.82 Inhibition of falcipain2 16509575
Falcipain 2 IC50 = 15.0 nM 7.82 Inhibition of Plasmodium falciparum recombinant falcipain-2 15588096
Cathepsin B IC50 = 16.0 nM 7.8 Inhibition of human cathepsin B 9784105
Procathepsin L IC50 = 16.0 nM 7.8 Inhibition of human cathepsin L1 -
Unchecked IC50 = 17.0 nM 7.77 Inhibition of Plasmodium falciparum recombinant falcipain-2 by microtiter plate ... 19586036
Unchecked IC50 = 17.0 nM 7.77 Inhibition of recombinant Plasmodium falciparum falcipain 2 after 30 mins by flu... 24530004
Unchecked IC50 = 17.0 nM 7.77 Inhibition of Plasmodium falciparum falcipain-2 using Z-Leu-Arg-AMC as substrate... 22192590
Unchecked IC50 = 20.0 nM 7.7 Inhibition of recombinant Plasmodium falciparum falcipain 2 incubated with compo... 23040894
Cruzipain IC50 = 20.0 nM 7.7 Inhibition of recombinant Trypanosoma cruzi cruzain using Z-FR-AMC as substrate ... 33992862

Literature References

PubMed DOI Target Context # Activities
25137549 10.1021/jm5009693 Plasmodium falciparum 33
10617079 10.1016/s0960-894x(99)00618-6 Cathepsin B 9
31284086 10.1016/j.ejmech.2019.06.062 Cruzipain 7
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
33992862 10.1016/j.bmc.2021.116213 Rhodesain 5
27475533 10.1016/j.bmc.2016.07.013 Cruzipain 5
23834438 10.1021/jm4006719 Calpain-1 catalytic subunit 4
19586036 10.1021/jm801622x Unchecked 4
18232656 10.1021/jm701141u Falcipain 2 3
28763614 10.1021/acs.jmedchem.7b00405 Procathepsin L 3
36098617 10.1021/acs.jnatprod.2c00521 Replicase polyprotein 1ab 3
18995931 10.1016/j.ejmech.2008.09.018 Papain 3
17088482 10.1128/aac.00840-06 Plasmodium falciparum 3
19715342 10.1021/jm900629w Unchecked 3
28763614 10.1021/acs.jmedchem.7b00405 Rhodesain 3
23040894 10.1016/j.bmc.2012.09.008 Unchecked 2
- 10.1007/s00044-011-9854-3 Falcipain 2 2
24077527 10.1016/j.ejmech.2013.08.037 Unchecked 2
18443109 10.1128/aac.00057-08 Plasmodium falciparum 2
22683112 10.1016/j.ejmech.2012.05.022 Unchecked 2

Data from ChEMBL 36 via Core Engine