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Compound Detail

CHEMBL92708

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

Basic Information

ChEMBL ID CHEMBL92708
Name CALPEPTIN
Phase Preclinical
Structure Type MOL
InChI Key PGGUOGKHUUUWAF-ROUUACIJSA-N
8
Targets
30
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

362.5
MW (Da)
3.20
ALogP
4
HBA
2
HBD
84.5
PSA (Ų)
0.59
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H30N2O4
MW 362.47
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 0.25

Activity Summary

IC50 21 meas. best 9.96
EC50 7 meas. best 7.94
Kd 1 meas. best 5.91
Ki 1 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin K
CHEMBL268
 IC50 9.96 9.96 0.1 2
Unchecked
CHEMBL612545
 IC50 8.4 7.48 4.0 3
Calpain-1 catalytic subunit
CHEMBL3891
 IC50 8.3 7.102 5.0 5
Calpain-1 catalytic subunit
CHEMBL3891
 Ki 8.15 8.15 7.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 7.94 6.22 11.6 7
Procathepsin L
CHEMBL3837
 IC50 7.36 7.25 44.0 2
Replicase polyprotein 1ab
CHEMBL4523582
 Kd 5.91 5.91 1220.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.61 5.1129 2430.0 7
Calpain-9
CHEMBL4523126
 IC50 5.55 5.55 2840.0 1
Human rhinovirus sp.
CHEMBL612470
 IC50 4.75 4.75 17700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin K IC50 = 0.11 nM 9.96 Inhibitory activity against recombinant human cathepsin K 14684342
Cathepsin K IC50 = 0.11 nM 9.96 Inhibitory activity against human cathepsin K 14741275
Unchecked IC50 = 4.0 nM 8.4 Inhibition of calpain-10 in rabbit mitochondrial matrix fractions by spectrofluo... 19072163
Calpain-1 catalytic subunit IC50 = 5.0 nM 8.3 Inhibitory activity evaluated against recombinant human calpain 1 -
Calpain-1 catalytic subunit Ki = 7.0 nM 8.15 The binding affinity against calpain. 10669559
Unchecked IC50 = 8.35 nM 8.08 Inhibition of wild-type CAPN5 (unknown origin) -
SARS-CoV-2 EC50 = 11.6 nM 7.94 Antiviral activity against SARS CoV-2 GFP infected in african green monkey Vero ... 38630165
Calpain-1 catalytic subunit IC50 = 40.0 nM 7.4 Inhibitory activity against Calpain 1 in platelets. 10669559
Procathepsin L IC50 = 43.98 nM 7.36 Inhibition of Cathepsin L (unknown origin) 37981443
Calpain-1 catalytic subunit IC50 = 52.0 nM 7.28 Inhibition of calpain (unknown origin) using Suc-LY-AMC as fluorogenic substrate... 30165342
Procathepsin L IC50 = 72.0 nM 7.14 Inhibition of cathepsin L (unknown origin) using Z-FR-AMC as substrate preincuba... 27318120
SARS-CoV-2 EC50 = 72.0 nM 7.14 Antiviral activity against SARS-CoV-2/human/DEU/HH-1/2020 infected in African gr... 36332548
SARS-CoV-2 EC50 = 72.0 nM 7.14 Antiviral activity against SARS-CoV-2 infected in african green monkey Vero E6 c... 37659195
Calpain-1 catalytic subunit IC50 = 297.0 nM 6.53 Inhibition of human erythrocytes mu-calpain using Pep1 as substrate incubated fo... 27318120
Calpain-1 catalytic subunit IC50 = 1000.0 nM 6.0 Inhibitory activity against calpain. 10669559
SARS-CoV-2 EC50 = 1033.0 nM 5.99 Antiviral activity against SARS-CoV-2 USA-WA1/2020 infected in African green mon... 37981443
Unchecked IC50 = 1100.0 nM 5.96 Inhibition of CAPN5 G267S mutant (unknown origin) using DABCYL-TPLKSPPPSPR-EDANS... -
SARS-CoV-2 EC50 = 1183.0 nM 5.93 Antiviral activity against SARS CoV-2 GFP infected in african green monkey Vero ... 38630165
Replicase polyprotein 1ab Kd = 1220.0 nM 5.91 Binding affinity to C-terminal His6-tagged recombinant SARS-CoV-2 MPro transfect... 36332548
Replicase polyprotein 1ab IC50 = 2430.0 nM 5.61 Inhibition of C-terminal His6-tagged recombinant SARS-CoV-2 MPro transfected in ... 36332548

Literature References

PubMed DOI Target Context # Activities
18024584 10.1073/pnas.0709695104 H4 11
36920850 10.1021/acs.jmedchem.3c00222 Unchecked 8
18391949 10.1038/nchembio.79 COS-7 4
18391949 10.1038/nchembio.79 PC-12 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
34271072 10.1016/j.bmcl.2021.128263 Replicase polyprotein 1ab 3
10669559 10.1021/jm990412m Calpain-1 catalytic subunit 3
37981443 10.1016/j.ejmech.2023.115923 SARS-CoV-2 3
27318120 10.1016/j.ejmech.2016.06.008 Calpain-1 catalytic subunit 3
38630165 10.1021/acs.jmedchem.3c02351 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
33191083 10.1016/j.bmc.2020.115860 Replicase polyprotein 1ab 2
36332548 10.1016/j.ejmech.2022.114857 Replicase polyprotein 1ab 2
30165342 10.1016/j.ejmech.2018.08.045 HK-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
18391949 10.1038/nchembio.79 HeLa 1
30165342 10.1016/j.ejmech.2018.08.045 Calpain-1 catalytic subunit 1
- 10.1016/S0960-894X(96)00537-9 Human rhinovirus sp. 1
38630165 10.1021/acs.jmedchem.3c02351 Procathepsin L 1
- 10.1016/S0960-894X(97)00063-2 Calpain-1 catalytic subunit 1

Data from ChEMBL 36 via Core Engine