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Compound Detail

CHEMBL115727

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COc1ccc(S(=O)(=O)N2CC(C)(C)CN(S(=O)(=O)c3ccc(OC)cc3)C2C(=O)NO)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL115727
Phase Preclinical
Structure Type MOL
InChI Key MCSWSPNUKWMZHM-UHFFFAOYSA-N
5
Targets
16
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

513.6
MW (Da)
1.26
ALogP
8
HBA
2
HBD
142.6
PSA (Ų)
0.42
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H27N3O8S2
MW 513.59
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness -0.43

Activity Summary

IC50 10 meas. best 8.74
Ki 6 meas. best 9.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Macrophage metalloelastase
CHEMBL4393
 Ki 9.21 8.965 0.6 2
Matrix metalloproteinase-9
CHEMBL321
 IC50 8.74 8.6267 1.8 3
Stromelysin-1
CHEMBL283
 Ki 7.75 7.75 18.0 1
Stromelysin-1
CHEMBL283
 IC50 7.74 7.6733 18.4 3
Interstitial collagenase
CHEMBL332
 IC50 7.62 7.62 24.0 2
Interstitial collagenase
CHEMBL332
 Ki 7.62 7.62 24.0 1
Matrix metalloproteinase-9
CHEMBL321
 Ki 7.52 7.52 30.0 1
Matrilysin
CHEMBL4073
 IC50 7.52 7.52 30.0 2
Matrilysin
CHEMBL4073
 Ki 7.52 7.52 30.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Macrophage metalloelastase Ki = 0.61 nM 9.21 Time dependent inhibition of human recombinant MMP12 by SPR assay -
Matrix metalloproteinase-9 IC50 = 1.8 nM 8.74 Inhibition of human recombinant MMP9 catalytic domain incubated for 20 mins by f... 22658537
Macrophage metalloelastase Ki = 1.9 nM 8.72 Inhibition of human recombinant MMP12 using Mca-Pro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2 ... -
Matrix metalloproteinase-9 IC50 = 2.7 nM 8.57 Inhibition of Matrix metalloprotease-9 9733482
Matrix metalloproteinase-9 IC50 = 2.7 nM 8.57 Inhibition of MMP9 (unknown origin) expressed in Escherichia coli BL21(DE3) usin... 28850227
Stromelysin-1 Ki = 18.0 nM 7.75 Inhibition of matrix metalloprotease-3 (MMP-3). 10669559
Stromelysin-1 IC50 = 18.4 nM 7.74 Inhibition of Matrix metalloprotease-3 9733482
Stromelysin-1 IC50 = 18.4 nM 7.74 Inhibition of truncated human recombinant MMP3 catalytic domain expressed in Esc... 28850227
Interstitial collagenase IC50 = 24.0 nM 7.62 Inhibition of Matrix metalloprotease-1 9733482
Interstitial collagenase IC50 = 24.0 nM 7.62 Inhibition of human interstitial recombinant N-terminal MMP1 expressed in Escher... 28850227
Interstitial collagenase Ki = 24.0 nM 7.62 Inhibition of matrix metalloprotease-1 (MMP-1). 10669559
Stromelysin-1 IC50 = 28.6 nM 7.54 Inhibition of human recombinant MMP3 catalytic domain incubated for 20 mins by f... 22658537
Matrilysin IC50 = 30.0 nM 7.52 Inhibition of Matrix metalloprotease-7 9733482
Matrilysin IC50 = 30.0 nM 7.52 Inhibition of MMP7 (unknown origin) expressed in Escherichia coli BL21(DE3) usin... 28850227
Matrilysin Ki = 30.0 nM 7.52 Inhibition of matrix metalloprotease-7 (MMP-7). 10669559
Matrix metalloproteinase-9 Ki = 30.0 nM 7.52 Inhibition of matrix metalloprotease-9 (MMP-9). 10669559

Literature References

PubMed DOI Target Context # Activities
- 10.1039/C2MD20268A Macrophage metalloelastase 2
22658537 10.1016/j.bmc.2012.04.063 Matrix metalloproteinase-9 2
22658537 10.1016/j.bmc.2012.04.063 Stromelysin-1 2
22658537 10.1016/j.bmc.2012.04.063 72 kDa type IV collagenase 1
28850227 10.1021/acs.jmedchem.7b00315 Interstitial collagenase 1
28850227 10.1021/acs.jmedchem.7b00315 Stromelysin-1 1
28850227 10.1021/acs.jmedchem.7b00315 Matrilysin 1
28850227 10.1021/acs.jmedchem.7b00315 Matrix metalloproteinase-9 1
22658537 10.1016/j.bmc.2012.04.063 Collagenase 3 1
22658537 10.1016/j.bmc.2012.04.063 Macrophage metalloelastase 1
10669559 10.1021/jm990412m Interstitial collagenase 1
22658537 10.1016/j.bmc.2012.04.063 Interstitial collagenase 1
9733482 10.1021/jm980253r Matrix metalloproteinase-9 1
9733482 10.1021/jm980253r Matrilysin 1
9733482 10.1021/jm980253r Stromelysin-1 1
9733482 10.1021/jm980253r Interstitial collagenase 1
10669559 10.1021/jm990412m Matrix metalloproteinase-9 1
10669559 10.1021/jm990412m Matrilysin 1
10669559 10.1021/jm990412m Stromelysin-1 1

Data from ChEMBL 36 via Core Engine