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Compound Detail

CHEMBL584365

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COc1ccc(-c2ccc(S(=O)(=O)c3ccccc3CC(=O)NO)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL584365
Phase Preclinical
Structure Type MOL
InChI Key DJZNIZCARKSSDE-UHFFFAOYSA-N
9
Targets
14
Activities
1
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

397.4
MW (Da)
3.24
ALogP
5
HBA
2
HBD
92.7
PSA (Ų)
0.49
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H19NO5S
MW 397.45
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.86

Activity Summary

IC50 14 meas. best 8.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Macrophage metalloelastase
CHEMBL4393
 IC50 8.32 8.32 4.8 2
72 kDa type IV collagenase
CHEMBL333
 IC50 8.01 8.01 9.7 2
Collagenase 3
CHEMBL280
 IC50 7.6 7.6 25.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 7.03 7.03 94.0 2
Neutrophil collagenase
CHEMBL4588
 IC50 6.92 6.92 120.0 1
Matrix metalloproteinase-16
CHEMBL2200
 IC50 6.89 6.89 130.0 1
Matrix metalloproteinase-14
CHEMBL3869
 IC50 6.15 6.15 710.0 2
Stromelysin-1
CHEMBL283
 IC50 5.8 5.8 1600.0 1
Interstitial collagenase
CHEMBL332
 IC50 5.08 5.08 8300.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Macrophage metalloelastase IC50 = 4.8 nM 8.32 Inhibition of autoactivated human pro-MMP12 after 4 hrs by fluorimetry 19775099
Macrophage metalloelastase IC50 = 4.8 nM 8.32 Inhibition of recombinant human MMP-12 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Al... 29727184
72 kDa type IV collagenase IC50 = 9.7 nM 8.01 Inhibition of para-aminophenylmercuric acetate-activated human recombinant pro-M... 19775099
72 kDa type IV collagenase IC50 = 9.7 nM 8.01 Inhibition of recombinant human MMP-2 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Ala... 29727184
Collagenase 3 IC50 = 25.0 nM 7.6 Inhibition of para-aminophenylmercuric acetate-activated human pro-MMP13 after 4... 19775099
Matrix metalloproteinase-9 IC50 = 94.0 nM 7.03 Inhibition of para-aminophenylmercuric acetate-activated human recombinant pro-M... 19775099
Matrix metalloproteinase-9 IC50 = 94.0 nM 7.03 Inhibition of recombinant human MMP-9 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Ala... 29727184
Neutrophil collagenase IC50 = 120.0 nM 6.92 Inhibition of para-aminophenylmercuric acetate-activated human pro-MMP8 after 4 ... 19775099
Matrix metalloproteinase-16 IC50 = 130.0 nM 6.89 Inhibition of human recombinant pro-MMP16 catalytic domain after 4 hrs by fluori... 19775099
Matrix metalloproteinase-14 IC50 = 710.0 nM 6.15 Inhibition of human recombinant pro-MMP14 catalytic domain after 4 hrs by fluori... 19775099
Matrix metalloproteinase-14 IC50 = 710.0 nM 6.15 Inhibition of recombinant human MMP-14 catalytic domain using Mca-Lys-Pro-Leu-Gl... 29727184
Stromelysin-1 IC50 = 1600.0 nM 5.8 Inhibition of trypsin activated human pro-MMP3 after 4 hrs by fluorimetry 19775099
Interstitial collagenase IC50 = 8300.0 nM 5.08 Inhibition of para-aminophenylmercuric acetate-activated human pro-MMP1 after 4 ... 19775099
Interstitial collagenase IC50 = 8300.0 nM 5.08 Inhibition of recombinant human MMP-1 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Ala... 29727184

Literature References

PubMed DOI Target Context # Activities
19775099 10.1021/jm900335a Macrophage metalloelastase 1
19775099 10.1021/jm900335a 72 kDa type IV collagenase 1
19775099 10.1021/jm900335a Collagenase 3 1
19775099 10.1021/jm900335a Matrix metalloproteinase-9 1
19775099 10.1021/jm900335a Neutrophil collagenase 1
19775099 10.1021/jm900335a Matrix metalloproteinase-16 1
19775099 10.1021/jm900335a Matrix metalloproteinase-14 1
19775099 10.1021/jm900335a Stromelysin-1 1
19775099 10.1021/jm900335a Interstitial collagenase 1
29727184 10.1021/acs.jmedchem.8b00096 Matrix metalloproteinase-9 1
29727184 10.1021/acs.jmedchem.8b00096 72 kDa type IV collagenase 1
29727184 10.1021/acs.jmedchem.8b00096 Macrophage metalloelastase 1
29727184 10.1021/acs.jmedchem.8b00096 Interstitial collagenase 1
29727184 10.1021/acs.jmedchem.8b00096 Matrix metalloproteinase-14 1
29727184 10.1021/acs.jmedchem.8b00096 No relevant target 1

Data from ChEMBL 36 via Core Engine