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Compound Detail

CHEMBL549695

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Cc1ccc(N)cc1C(=O)N[C@H](C)c1cccc2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL549695
Phase Preclinical
Structure Type MOL
InChI Key UVERBUNNCOKGNZ-CQSZACIVSA-N
5
Targets
45
Activities
4
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

304.4
MW (Da)
4.22
ALogP
2
HBA
2
HBD
55.1
PSA (Ų)
0.71
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H20N2O
MW 304.39
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -1.17

Activity Summary

IC50 25 meas. best 6.22
EC50 17 meas. best 5.5
Kd 2 meas. best 5.57
Ki 1 meas. best 6.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 6.22 5.7347 600.0 19
Replicase polyprotein 1ab
CHEMBL5118
 IC50 6.22 6.22 600.0 1
Replicase polyprotein 1ab
CHEMBL5118
 Ki 6.22 6.22 600.0 1
Unchecked
CHEMBL612545
 IC50 6.22 5.918 600.0 5
Unchecked
CHEMBL612545
 Kd 5.57 5.57 2700.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 5.5 4.6217 3180.0 12
SARS-CoV
CHEMBL4303836
 EC50 5.0 4.88 10000.0 5
Replicase polyprotein 1ab
CHEMBL4523582
 Kd 4.97 4.97 10790.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 27.0 mL.min-1.kg-1 Homo sapiens
CL 67.4 mL.min-1.g-1 Mus musculus
CL 267000.0 mL.min-1.g-1 Mus musculus
T1/2 0.75 hr Homo sapiens
T1/2 0.1267 hr Mus musculus
T1/2 0.44 hr Homo sapiens
T1/2 0.3433 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Replicase polyprotein 1ab Ki = 600.0 nM 6.22 Binding affinity to SARS-CoV-1 papain-like protease assessed as inhibition const... 37770002
Unchecked IC50 = 600.0 nM 6.22 Inhibition of SARS-CoV-1 papain-like protease incubated for 1 hr 39102360
Replicase polyprotein 1ab IC50 = 600.0 nM 6.22 Inhibition of SARS-CoV-1 papain-like protease 37770002
Replicase polyprotein 1ab IC50 = 600.0 nM 6.22 Inhibition of SARS CoV-2 PL protease (1541 to 1855 residues) incubated for 3 hrs... 33186044
Unchecked IC50 = 600.0 nM 6.22 Inhibition of SARS-CoV PL-pro by microplate reader analysis 23231439
Replicase polyprotein 1ab IC50 = 800.0 nM 6.1 Inhibition of His tagged SARS-CoV-2 PLpro using Z-RLRGG-AMC as substrate assesse... 36651644
Replicase polyprotein 1ab IC50 = 900.0 nM 6.05 Inhibition of SARS-CoV-2 papain-like protease 37770002
Replicase polyprotein 1ab IC50 = 1390.0 nM 5.86 Inhibition of full-length SARS-CoV-2 papain-like protease (1564 to 1878 residues... 35620927
Replicase polyprotein 1ab IC50 = 1390.0 nM 5.86 Inhibition of SARS-CoV-2 PLpro 36503248
Replicase polyprotein 1ab IC50 = 1610.0 nM 5.79 Inhibition of SARS-CoV-2 PLpro 35797899
Unchecked IC50 = 1610.0 nM 5.79 Inhibition of SARS-CoV-2 PLpro using Z-RLRGG-AMC as substrate preincubated for 1... 34665619
Replicase polyprotein 1ab IC50 = 1610.0 nM 5.79 Inhibition of N-terminal his-tagged SARS CoV-2 PL protease (1564 to 1878 residue... 39102360
Unchecked IC50 = 1670.0 nM 5.78 Inhibition of SARS CoV-2 papain-like protease using Z-Arg-Leu-Arg-Gly-Gly-AMC as... 34571172
Replicase polyprotein 1ab IC50 = 1700.0 nM 5.77 Inhibition of SARS-CoV2 PLpro using Z-RLRGG-AMC as substrate preincubated for 10... 38871484
Replicase polyprotein 1ab IC50 = 1789.0 nM 5.75 Inhibition of N-terminal 3xFlag-His6-tagged SARS-CoV-2 papain-like protease nsp3... 35620927
Replicase polyprotein 1ab IC50 = 2050.0 nM 5.69 Inhibition of C-terminal His-tagged SARS-CoV-2 PLpro preincubated for 1 hrs foll... 38065031
Replicase polyprotein 1ab IC50 = 2050.0 nM 5.69 Inhibition of C-terminal His-tagged SARS-CoV-2 PLpro BetaCoV/Wuhan/WIV04/2019 st... 36966652
Replicase polyprotein 1ab IC50 = 2100.0 nM 5.68 Inhibition of N-terminal His/TEV-tagged SARS-CoV-2 papain-like protease nsp3 (74... 35620927
Replicase polyprotein 1ab IC50 = 2100.0 nM 5.68 Inhibition of SARS-CoV2 PLpro (746 to 1060 residues) expressed in Escherichia co... 38871484
Replicase polyprotein 1ab IC50 = 2300.0 nM 5.64 Inhibition of SARS-CoV-2 papain-like protease nsp3 expressed in Escherichia coli... 35620927

Literature References

PubMed DOI Target Context # Activities
38871484 10.1021/acs.jmedchem.4c00534 ADMET 10
35620927 10.1021/acs.jmedchem.2c00303 Replicase polyprotein 1ab 5
34665619 10.1021/acs.jmedchem.1c01307 Unchecked 5
38065031 10.1016/j.ejmech.2023.116011 ADMET 3
39140055 10.1021/acsmedchemlett.4c00238 Replicase polyprotein 1ab 3
35797899 10.1016/j.ejmech.2022.114572 Replicase polyprotein 1ab 3
38871484 10.1021/acs.jmedchem.4c00534 SARS-CoV-2 3
37075625 10.1016/j.ejmech.2023.115380 Replicase polyprotein 1ab 3
38871484 10.1021/acs.jmedchem.4c00534 Replicase polyprotein 1ab 3
37770002 10.1016/j.bmcl.2023.129489 Replicase polyprotein 1ab 3
34665619 10.1021/acs.jmedchem.1c01307 SARS-CoV-2 2
36651644 10.1021/acs.jnatprod.2c00843 Replicase polyprotein 1ab 2
38065031 10.1016/j.ejmech.2023.116011 SARS-CoV-2 2
33186044 10.1021/acs.jmedchem.0c01140 SARS-CoV-2 2
23231439 10.1021/jm301580n Unchecked 2
35620927 10.1021/acs.jmedchem.2c00303 SARS-CoV-2 2
35797899 10.1016/j.ejmech.2022.114572 SARS-CoV-2 1
34571172 10.1016/j.ejmech.2021.113863 Unchecked 1
32665808 10.1021/acsmedchemlett.0c00254 SARS-CoV 1
23231439 10.1021/jm301580n SARS-CoV 1

Data from ChEMBL 36 via Core Engine