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Compound Detail

CHEMBL3427166

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CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C[C@@H]1CCNC1=O)C(O)S(=O)(=O)[O-].[Na+]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3427166
Phase Preclinical
Structure Type MOL
InChI Key BSPJDKCMFIPBAW-KVIMGBSASA-M
Parent Compound CHEMBL3559293
Active Moiety CHEMBL3559293
13
Targets
74
Activities
4
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

485.6
MW (Da)
0.54
ALogP
7
HBA
5
HBD
171.1
PSA (Ų)
0.28
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 C21H30N3NaO8S
MW 507.54
Aromatic Rings 1
Heavy Atoms 33
NP-Likeness 0.25

Activity Summary

IC50 42 meas. best 9.6
EC50 29 meas. best 7.66
Ki 2 meas. best 7.22
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Procathepsin L
CHEMBL3837
 IC50 9.6 7.8 0.2 2
Cathepsin K
CHEMBL268
 IC50 9.25 9.25 0.6 1
SARS-CoV-2
CHEMBL4303835
 EC50 7.66 6.115 21.7 24
Cathepsin S
CHEMBL2954
 IC50 7.64 7.64 23.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 7.52 7.0275 30.0 24
Unchecked
CHEMBL612545
 IC50 7.46 6.446 35.0 10
Replicase polyprotein 1a
CHEMBL3927
 IC50 7.3 7.3 50.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 Ki 7.22 7.125 60.0 2
Cathepsin F
CHEMBL2517
 IC50 7.13 7.13 74.0 1
Human coronavirus OC43
CHEMBL5209665
 EC50 6.77 6.77 171.0 1
SARS-CoV-2
CHEMBL4303835
 IC50 6.7 6.7 200.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.52 6.52 300.0 1
Norovirus
CHEMBL4296584
 EC50 6.52 6.52 300.0 1
Human coronavirus 229E
CHEMBL613837
 EC50 6.46 6.46 350.0 1
Cathepsin B
CHEMBL4072
 IC50 5.85 5.85 1400.0 1
Unchecked
CHEMBL612545
 EC50 5.5 5.5 3150.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 3.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Procathepsin L IC50 = 0.25 nM 9.6 Inhibition of human cathepsin L 34778773
Cathepsin K IC50 = 0.56 nM 9.25 Inhibition of human Cathepsin K using Ac-LR-AMC as fluorogenic substrate incubat... 36107752
SARS-CoV-2 EC50 = 21.7 nM 7.66 Antiviral activity against SARS-CoV-2 variant Omicron BA.2 infected in African g... 37229831
Cathepsin S IC50 = 23.0 nM 7.64 Inhibition of human cathepsin S 34778773
SARS-CoV-2 EC50 = 27.0 nM 7.57 Antiviral activity against SARS-CoV-2 Wuhan-HU-1 infected in HEK293T cells asses... 37080108
Replicase polyprotein 1ab IC50 = 29.99 nM 7.52 Inhibition of SARS-CoV-2 MPro 33191083
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS-CoV-2 MPro 33191083
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS CoV-2 main protease expressed in Escherichia coli BL21 (DE3) ... 35688005
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS-CoV-2 (BetaCoV/Wuhan/WIV04/2019) MPro expressed in Escherichi... 33191083
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS CoV-2 3CL protease using dabcyl-KTSAVLQ/SGFRKME-edans as subs... 33186044
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS-CoV-2 main protease 36475694
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS-CoV-2 Main protease 37244162
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of His-tagged SARS-CoV-2 Main protease BetaCoV/Wuhan/WIV04/2019 expre... 37244162
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS-CoV-2 main protease 37561993
Replicase polyprotein 1ab IC50 = 30.0 nM 7.52 Inhibition of SARS-CoV-2 BetaCoV/Wuhan/WIV04/2019 Main protease expressed in Esc... 37517202
Replicase polyprotein 1ab IC50 = 33.0 nM 7.48 Inhibition of SARS-CoV-2 main protease using MCA-AVLQSGFR-Lys(Dnp)-Lys-NH2 as fl... 36107752
Unchecked IC50 = 35.0 nM 7.46 Non-covalent inhibition of SARS-Cov -Mpro incubated for 30 mins using FRET subst... 33891389
Replicase polyprotein 1a IC50 = 50.0 nM 7.3 Inhibition of SARS-CoV MPro transfected in Escherichia coli BL21 (DE3) using Dab... 37659195
Replicase polyprotein 1ab Ki = 60.0 nM 7.22 Binding affinity to SARS CoV-2 3CL protease using dabcyl-KTSAVLQ/SGFRKME-edans a... 33186044
Cathepsin F IC50 = 74.0 nM 7.13 Inhibition of human Cathepsin F using Z-Phe-Arg-AMC as fluorogenic substrate inc... 36107752

Literature References

PubMed DOI Target Context # Activities
33891389 10.1021/acs.jmedchem.1c00509 Unchecked 8
33891389 10.1021/acs.jmedchem.1c00509 Replicase polyprotein 1ab 4
28671827 10.1021/acs.jmedchem.7b00497 Serum 4
33186044 10.1021/acs.jmedchem.0c01140 Unchecked 3
33191083 10.1016/j.bmc.2020.115860 Replicase polyprotein 1ab 3
33186044 10.1021/acs.jmedchem.0c01140 Replicase polyprotein 1ab 3
38941718 10.1016/j.ejmech.2024.116629 SARS-CoV-2 3
36169610 10.1021/acs.jmedchem.2c01005 Replicase polyprotein 1ab 3
37609780 10.1021/acs.jnatprod.3c00633 Replicase polyprotein 1ab 3
34778773 10.1039/D1MD00247C SARS-CoV-2 2
33186044 10.1021/acs.jmedchem.0c01140 SARS-CoV-2 2
34778773 10.1039/D1MD00247C A549 2
34778773 10.1039/D1MD00247C Cathepsin S 2
34242027 10.1021/acs.jmedchem.1c00616 ADMET 2
36757959 10.1021/acs.jmedchem.2c01627 Replicase polyprotein 1ab 2
34118724 10.1016/j.ejmech.2021.113584 SARS-CoV-2 2
36970153 10.1039/d2md00149g Replicase polyprotein 1ab 2
28671827 10.1021/acs.jmedchem.7b00497 Unchecked 2
28671827 10.1021/acs.jmedchem.7b00497 Liver 2
34778773 10.1039/D1MD00247C Cathepsin B 2

Data from ChEMBL 36 via Core Engine