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Compound Detail

CHEMBL267178

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COc1ccc(S(=O)(=O)N(Cc2cccnc2)[C@@H](C(=O)NO)C(C)C)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267178
Phase Preclinical
Structure Type MOL
InChI Key BSIZUMJRKYHEBR-QGZVFWFLSA-N
7
Targets
19
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

393.5
MW (Da)
1.81
ALogP
6
HBA
2
HBD
108.8
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H23N3O5S
MW 393.47
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -1.06

Activity Summary

IC50 19 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
72 kDa type IV collagenase
CHEMBL333
 IC50 8.4 7.795 4.0 4
Matrix metalloproteinase-9
CHEMBL321
 IC50 8.32 7.956 4.8 5
Collagenase 3
CHEMBL280
 IC50 8.22 8.01 6.0 2
Neutrophil collagenase
CHEMBL4588
 IC50 8.0 7.98 10.0 2
Stromelysin-1
CHEMBL283
 IC50 7.89 7.6433 13.0 3
Matrix metalloproteinase-14
CHEMBL3869
 IC50 7.64 7.64 23.0 1
Interstitial collagenase
CHEMBL332
 IC50 7.48 7.365 33.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase IC50 = 4.0 nM 8.4 Inhibition of human MMP2 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3... 30954331
Matrix metalloproteinase-9 IC50 = 4.8 nM 8.32 Inhibition of recombinant human proMMP9 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-A... 30522899
Collagenase 3 IC50 = 6.0 nM 8.22 Inhibition of MMP-13 (unknown origin) 32224379
Matrix metalloproteinase-9 IC50 = 8.0 nM 8.1 Inhibition of MMP-9 (unknown origin) 32224379
Neutrophil collagenase IC50 = 10.0 nM 8.0 Inhibition of recombinant human MMP8 (Phe21 to Gly467 residues) expressed in mou... 28756264
Matrix metalloproteinase-9 IC50 = 10.0 nM 8.0 Inhibition of recombinant human MMP9 (Ala20 to Asp707 residues) expressed in CHO... 28756264
Neutrophil collagenase IC50 = 11.0 nM 7.96 Inhibition of human MMP8 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3... 30954331
Matrix metalloproteinase-9 IC50 = 11.0 nM 7.96 Inhibition of human MMP9 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3... 30954331
72 kDa type IV collagenase IC50 = 11.0 nM 7.96 Inhibition of MMP-2 (unknown origin) 32224379
Stromelysin-1 IC50 = 13.0 nM 7.89 Inhibition of MMP-3 (unknown origin) 32224379
Collagenase 3 IC50 = 16.0 nM 7.8 Inhibition of human MMP13 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(... 30954331
Matrix metalloproteinase-14 IC50 = 23.0 nM 7.64 Inhibition of recombinant human MT1-MMP catalytic domain using Mca-Lys-Pro-Leu-G... 30522899
72 kDa type IV collagenase IC50 = 25.0 nM 7.6 Inhibition of recombinant human proMMP2 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-A... 30522899
Stromelysin-1 IC50 = 30.0 nM 7.52 Inhibition of recombinant human MMP3 (Tyr18 to Cys477 residues) expressed in mou... 28756264
Stromelysin-1 IC50 = 30.0 nM 7.52 Inhibition of recombinant human MMP3 preincubated for 30 mins followed by McaPro... 29921475
Interstitial collagenase IC50 = 33.0 nM 7.48 Inhibition of MMP-1 (unknown origin) 32224379
Matrix metalloproteinase-9 IC50 = 40.0 nM 7.4 Inhibition of recombinant human MMP9 preincubated for 30 mins followed by McaPro... 29921475
Interstitial collagenase IC50 = 56.0 nM 7.25 Inhibition of recombinant human pro-MMP1 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-... 30522899
72 kDa type IV collagenase IC50 = 60.0 nM 7.22 Inhibition of recombinant human MMP2 preincubated for 30 mins followed by McaPro... 29921475

Literature References

PubMed DOI Target Context # Activities
28337319 10.1021/acsmedchemlett.6b00446 Matrix metalloproteinase-9 3
30522899 10.1016/j.bmc.2018.11.041 Interstitial collagenase 1
32224379 10.1016/j.ejmech.2020.112260 Collagenase 3 1
32224379 10.1016/j.ejmech.2020.112260 Stromelysin-1 1
32224379 10.1016/j.ejmech.2020.112260 Interstitial collagenase 1
32224379 10.1016/j.ejmech.2020.112260 72 kDa type IV collagenase 1
32224379 10.1016/j.ejmech.2020.112260 Matrix metalloproteinase-9 1
30954331 10.1016/j.bmc.2019.03.056 Collagenase 3 1
30954331 10.1016/j.bmc.2019.03.056 Matrix metalloproteinase-9 1
30954331 10.1016/j.bmc.2019.03.056 Neutrophil collagenase 1
30954331 10.1016/j.bmc.2019.03.056 72 kDa type IV collagenase 1
30522899 10.1016/j.bmc.2018.11.041 72 kDa type IV collagenase 1
30522899 10.1016/j.bmc.2018.11.041 Matrix metalloproteinase-9 1
30522899 10.1016/j.bmc.2018.11.041 Matrix metalloproteinase-14 1
29921475 10.1016/j.bmcl.2018.06.024 Matrix metalloproteinase-9 1
29921475 10.1016/j.bmcl.2018.06.024 Stromelysin-1 1
29921475 10.1016/j.bmcl.2018.06.024 72 kDa type IV collagenase 1
28756264 10.1016/j.ejmech.2017.07.020 Matrix metalloproteinase-9 1
28756264 10.1016/j.ejmech.2017.07.020 Neutrophil collagenase 1
28756264 10.1016/j.ejmech.2017.07.020 Stromelysin-1 1

Data from ChEMBL 36 via Core Engine