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Compound Detail

CHEMBL181244

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CC(C)ON(CC(=O)NO)S(=O)(=O)c1ccc(-c2ccccc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL181244
Phase Preclinical
Structure Type MOL
InChI Key PHGLPDURIUEELR-UHFFFAOYSA-N
8
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

364.4
MW (Da)
2.19
ALogP
5
HBA
2
HBD
95.9
PSA (Ų)
0.58
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H20N2O5S
MW 364.42
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.81

Activity Summary

IC50 27 meas. best 7.92
Ki 2 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
72 kDa type IV collagenase
CHEMBL333
 IC50 7.92 7.92 12.0 6
72 kDa type IV collagenase
CHEMBL333
 Ki 7.89 7.89 13.0 1
Collagenase 3
CHEMBL280
 Ki 7.7 7.7 20.0 1
Collagenase 3
CHEMBL280
 IC50 7.6 7.475 25.0 2
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.7 6.7 200.0 6
Neutrophil collagenase
CHEMBL4588
 IC50 6.58 6.58 260.0 1
Matrix metalloproteinase-16
CHEMBL2200
 IC50 6.05 6.05 900.0 1
Matrix metalloproteinase-14
CHEMBL3869
 IC50 5.64 5.64 2300.0 2
Interstitial collagenase
CHEMBL332
 IC50 5.54 5.1267 2900.0 3
Stromelysin-1
CHEMBL283
 IC50 5.35 5.326 4500.0 5

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase IC50 = 12.0 nM 7.92 Inhibition of MMP2 18790648
72 kDa type IV collagenase IC50 = 12.0 nM 7.92 Inhibition of MMP2 19606871
72 kDa type IV collagenase IC50 = 12.0 nM 7.92 Inhibition of MMP2 by fluorometric assay 20180536
72 kDa type IV collagenase IC50 = 12.0 nM 7.92 Inhibition of MMP2 (unknown origin) 23287054
72 kDa type IV collagenase IC50 = 12.0 nM 7.92 Inhibition of MMP-2 (unknown origin) activity using Mca-Pro-Leu-Gly-Leu-Dpa-Ala-... 35969157
72 kDa type IV collagenase IC50 = 12.0 nM 7.92 Inhibition of human matrix metalloprotease-2 15713379
72 kDa type IV collagenase Ki = 13.0 nM 7.89 Inhibition of MMP2 19606871
Collagenase 3 Ki = 20.0 nM 7.7 Inhibition of MMP13 19606871
Collagenase 3 IC50 = 25.0 nM 7.6 Inhibition of MMP13-mediated collagen degradation by SDS-PAGE 19606871
Collagenase 3 IC50 = 45.0 nM 7.35 Inhibition of MMP13 19606871
Matrix metalloproteinase-9 IC50 = 200.0 nM 6.7 Inhibition of MMP9 18790648
Matrix metalloproteinase-9 IC50 = 200.0 nM 6.7 Inhibition of MMP-9 (unknown origin) activity using Mca-Pro-Leu-Gly-Leu-Dpa-Ala-... 35969157
Matrix metalloproteinase-9 IC50 = 200.0 nM 6.7 Inhibition of MMP9 (unknown origin) 23287054
Matrix metalloproteinase-9 IC50 = 200.0 nM 6.7 Inhibition of MMP9 by fluorometric assay 20180536
Matrix metalloproteinase-9 IC50 = 200.0 nM 6.7 Inhibition of MMP9 19606871
Matrix metalloproteinase-9 IC50 = 200.0 nM 6.7 Inhibition of human matrix metalloprotease-9 15713379
Neutrophil collagenase IC50 = 260.0 nM 6.58 Inhibition of MMP8 19606871
Matrix metalloproteinase-16 IC50 = 900.0 nM 6.05 Inhibition of human recombinant MMP16 19606871
Matrix metalloproteinase-14 IC50 = 2300.0 nM 5.64 Inhibition of human recombinant MMP14 19606871
Matrix metalloproteinase-14 IC50 = 2300.0 nM 5.64 Inhibition of human recombinant MMP14 by fluorometric assay 20180536

Literature References

PubMed DOI Target Context # Activities
19606871 10.1021/jm900261f Unchecked 5
15713379 10.1016/j.bmcl.2005.01.024 Unchecked 3
19606871 10.1021/jm900261f Collagenase 3 3
15713379 10.1016/j.bmcl.2005.01.024 Matrix metalloproteinase-14 2
20180536 10.1021/jm901868z Disintegrin and metalloproteinase domain-containing protein 17 2
19606871 10.1021/jm900261f 72 kDa type IV collagenase 2
19606871 10.1021/jm900261f Interstitial collagenase 2
15713379 10.1016/j.bmcl.2005.01.024 Matrix metalloproteinase-9 1
18790648 10.1016/j.bmc.2008.08.058 Matrix metalloproteinase-9 1
18790648 10.1016/j.bmc.2008.08.058 Matrilysin 1
18790648 10.1016/j.bmc.2008.08.058 Stromelysin-1 1
18790648 10.1016/j.bmc.2008.08.058 72 kDa type IV collagenase 1
18790648 10.1016/j.bmc.2008.08.058 Interstitial collagenase 1
15713379 10.1016/j.bmcl.2005.01.024 Matrilysin 1
15713379 10.1016/j.bmcl.2005.01.024 Matrix metalloproteinase (2 and 3) 1
35969157 10.1021/acs.jmedchem.1c01855 Matrix metalloproteinase-9 1
19606871 10.1021/jm900261f Neutrophil collagenase 1
19606871 10.1021/jm900261f Matrix metalloproteinase-9 1
15713379 10.1016/j.bmcl.2005.01.024 Stromelysin-1 1
15713379 10.1016/j.bmcl.2005.01.024 72 kDa type IV collagenase 1

Data from ChEMBL 36 via Core Engine