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Compound Detail

CHEMBL423112

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CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(C=O)Cc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL423112
Phase Preclinical
Structure Type MOL
InChI Key NGBKFLTYGSREKK-ANYOKISRSA-N
14
Targets
46
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

382.5
MW (Da)
2.86
ALogP
4
HBA
2
HBD
84.5
PSA (Ų)
0.65
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H26N2O4
MW 382.46
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.02

Activity Summary

IC50 34 meas. best 8.6
Ki 9 meas. best 8.0
EC50 3 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Procathepsin L
CHEMBL3837
 IC50 8.6 7.9025 2.5 4
Calpain-1 catalytic subunit
CHEMBL4062
 Ki 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
 Ki 8.0 8.0 10.0 1
Calpain-1 catalytic subunit
CHEMBL3891
 Ki 8.0 7.8625 10.0 4
Calpain-1 catalytic subunit
CHEMBL3147
 Ki 8.0 8.0 10.0 1
Calpain-1 catalytic subunit
CHEMBL3891
 IC50 7.96 7.0655 11.0 11
Cathepsin B
CHEMBL4072
 Ki 7.75 7.675 18.0 2
Calpain-1 catalytic subunit
CHEMBL4062
 IC50 7.7 7.7 20.0 1
Calpain 1
CHEMBL2111357
 IC50 7.4 7.4 40.0 1
Cathepsin B
CHEMBL4072
 IC50 7.02 6.63 95.8 3
SARS-CoV
CHEMBL4303836
 EC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 EC50 7.0 7.0 100.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 6.66 6.66 220.0 1
Calpain-2 catalytic subunit
CHEMBL2382
 IC50 6.46 6.46 350.0 1
Unchecked
CHEMBL612545
 IC50 6.16 5.7733 700.0 3
Calpain-9
CHEMBL4523126
 IC50 5.79 5.79 1610.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.5 5.3429 3162.3 7
Falcipain 2B
CHEMBL3488
 IC50 5.3 5.3 5000.0 1
Falcipain 2
CHEMBL5800
 IC50 5.3 5.3 5000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Procathepsin L IC50 = 2.5 nM 8.6 Inhibition of human Cathepsin L using Z-Phe-Arg-AMC as substrate incubated for 4... 33486200
Procathepsin L IC50 = 2.5 nM 8.6 Inhibition of human recombinant Cathepsin L assessed as Kinact using Z-FR-AMC as... 32539378
Procathepsin L IC50 = 3.1 nM 8.51 Inhibition of cathepsin L (unknown origin) using Z-FR-AMC as substrate preincuba... 27318120
Calpain-1 catalytic subunit Ki = 10.0 nM 8.0 Inhibitory activity against chicken gizzard smooth muscle calpain 10021915
Calpain-1 catalytic subunit Ki = 10.0 nM 8.0 Inhibition of pig erythrocyte mu-calpain by fluorometric assay 18636690
Unchecked Ki = 10.0 nM 8.0 Binding affinity for rat erythrocyte calpain 15896956
Calpain-1 catalytic subunit Ki = 10.0 nM 8.0 Tested for inhibitory activity against calpain. 10476870
Calpain-1 catalytic subunit IC50 = 11.0 nM 7.96 Inhibitory activity using recombinant human Calpain 1 with Suc-Leu-Tyr-MNA as su... -
Calpain-1 catalytic subunit Ki = 15.0 nM 7.82 Inhibition of calpain, using human mu-calpain isolated from erythrocytes and Suc... 11992771
Calpain-1 catalytic subunit Ki = 15.0 nM 7.82 Inhibition of Suc-Leu-Tyr-AMC binding to human mu-calpain from erythrocytes 11012026
Calpain-1 catalytic subunit Ki = 15.5 nM 7.81 Inhibitory activity against human Calpain 1 isolated from erythrocytes 12773044
Calpain-1 catalytic subunit IC50 = 17.0 nM 7.77 Inhibitory activity of compound against recombinant human Calpain 1 -
Cathepsin B Ki = 18.0 nM 7.75 Inhibition of cathepsin B 12773044
Calpain-1 catalytic subunit IC50 = 20.0 nM 7.7 Inhibitory activity against porcine calpain I using Suc-Leu-Tyr-AMC fluorogenic ... 16185867
Cathepsin B Ki = 25.0 nM 7.6 Inhibition of human Cathepsin B 11012026
Calpain 1 IC50 = 40.0 nM 7.4 Inhibition of Calpain 1 by [3H]acetyl-casein assay -
Calpain-1 catalytic subunit IC50 = 56.0 nM 7.25 Inhibition of human CAPN1 18571418
Calpain-1 catalytic subunit IC50 = 70.0 nM 7.16 Inhibition of human erythrocytes mu-calpain 19041242
Calpain-1 catalytic subunit IC50 = 70.0 nM 7.16 Inhibition of human erythrocytes mu-calpain by spectrofluorimeter 18396356
Calpain-1 catalytic subunit IC50 = 70.0 nM 7.16 Inhibition of human mu-calpain 18024028

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
15911268 10.1016/j.bmcl.2005.03.095 Procathepsin L 3
15911268 10.1016/j.bmcl.2005.03.095 Cathepsin B 3
27318120 10.1016/j.ejmech.2016.06.008 Calpain-1 catalytic subunit 3
- 10.1016/S0960-894X(96)00286-7 Calpain-1 catalytic subunit 2
19419206 10.1021/jm8014734 Calpain-1 catalytic subunit 2
12773044 10.1021/jm0210717 Calpain-1 catalytic subunit 2
11992771 10.1016/s0960-894x(02)00176-2 Unchecked 1
32539378 10.1021/acs.jmedchem.0c00502 Unchecked 1
11992771 10.1016/s0960-894x(02)00176-2 Procathepsin L 1
12773044 10.1021/jm0210717 Cathepsin B 1
11012026 10.1016/s0960-894x(00)00430-3 Calpain-1 catalytic subunit 1
11012026 10.1016/s0960-894x(00)00430-3 Cathepsin B 1
11012026 10.1016/s0960-894x(00)00430-3 Unchecked 1
11992771 10.1016/s0960-894x(02)00176-2 Cathepsin B 1
15896956 10.1016/j.bmcl.2005.04.031 Unchecked 1
15911268 10.1016/j.bmcl.2005.03.095 Calpain-1 catalytic subunit 1
11992771 10.1016/s0960-894x(02)00176-2 Calpain-1 catalytic subunit 1
10476870 10.1016/s0960-894x(99)00391-1 Calpain-1 catalytic subunit 1
10021915 10.1016/s0960-894x(98)00704-5 Calpain-1 catalytic subunit 1

Data from ChEMBL 36 via Core Engine