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Compound Detail

CHEMBL179288

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

Basic Information

ChEMBL ID CHEMBL179288
Phase Preclinical
Structure Type MOL
InChI Key DGZZVIWCMGVHGV-LJQANCHMSA-N
11
Targets
22
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

406.5
MW (Da)
3.21
ALogP
5
HBA
2
HBD
95.9
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H26N2O5S
MW 406.50
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.60

Activity Summary

IC50 22 meas. best 10.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
72 kDa type IV collagenase
CHEMBL333
 IC50 10.05 9.4167 0.1 3
Macrophage metalloelastase
CHEMBL4393
 IC50 9.7 9.7 0.2 1
Neutrophil collagenase
CHEMBL4588
 IC50 8.8 8.8 1.6 2
Collagenase 3
CHEMBL280
 IC50 8.39 8.39 4.1 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 8.17 8.17 6.7 3
Matrix metalloproteinase-14
CHEMBL3869
 IC50 8.01 8.01 9.8 2
Stromelysin-1
CHEMBL283
 IC50 7.3 7.3 50.0 2
Matrix metalloproteinase-16
CHEMBL2200
 IC50 7.29 7.29 51.0 1
Interstitial collagenase
CHEMBL332
 IC50 6.83 6.57 147.0 2
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 4.85 4.85 14000.0 1
Elastase
CHEMBL1075146
 IC50 4.24 4.24 57000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase IC50 = 0.09 nM 10.05 Inhibition of human matrix metalloprotease-2 15713379
Macrophage metalloelastase IC50 = 0.2 nM 9.7 Inhibition of autoactivated human pro-MMP12 after 4 hrs by fluorimetry 19775099
72 kDa type IV collagenase IC50 = 0.8 nM 9.1 Inhibition of para-aminophenylmercuric acetate-activated human recombinant pro-M... 19775099
72 kDa type IV collagenase IC50 = 0.8 nM 9.1 Inhibition of recombinant human MMP2 after 2 hrs using FS-6 as substrate by fluo... 26638045
Neutrophil collagenase IC50 = 1.6 nM 8.8 Inhibition of human matrix metalloprotease-8 15713379
Neutrophil collagenase IC50 = 1.6 nM 8.8 Inhibition of para-aminophenylmercuric acetate-activated human pro-MMP8 after 4 ... 19775099
Collagenase 3 IC50 = 4.1 nM 8.39 Inhibition of para-aminophenylmercuric acetate-activated human pro-MMP13 after 4... 19775099
Matrix metalloproteinase-9 IC50 = 6.7 nM 8.17 Inhibition of recombinant human MMP9 after 2 hrs using FS-6 as substrate by fluo... 26638045
Matrix metalloproteinase-9 IC50 = 6.7 nM 8.17 Inhibition of para-aminophenylmercuric acetate-activated human recombinant pro-M... 19775099
Matrix metalloproteinase-9 IC50 = 6.7 nM 8.17 Inhibition of human matrix metalloprotease-9 15713379
Matrix metalloproteinase-14 IC50 = 9.8 nM 8.01 Inhibition of human matrix metalloprotease-14 15713379
Matrix metalloproteinase-14 IC50 = 9.8 nM 8.01 Inhibition of human recombinant pro-MMP14 catalytic domain after 4 hrs by fluori... 19775099
Stromelysin-1 IC50 = 50.0 nM 7.3 Inhibition of human matrix metalloprotease-3 15713379
Stromelysin-1 IC50 = 50.0 nM 7.3 Inhibition of trypsin activated human pro-MMP3 after 4 hrs by fluorimetry 19775099
Matrix metalloproteinase-16 IC50 = 51.0 nM 7.29 Inhibition of human recombinant pro-MMP16 catalytic domain after 4 hrs by fluori... 19775099
Interstitial collagenase IC50 = 147.0 nM 6.83 Inhibition of human matrix metalloprotease-1 15713379
Interstitial collagenase IC50 = 490.0 nM 6.31 Inhibition of para-aminophenylmercuric acetate-activated human pro-MMP1 after 4 ... 19775099
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 14000.0 nM 4.85 Inhibition of recombinant human ADAM17 after 30 mins using FS-6 as substrate by ... 26638045
Elastase IC50 = 57000.0 nM 4.24 Inhibition of Bacillus thermoproteolyticus pseudolysin pretreated with compound ... 26638045

Literature References

PubMed DOI Target Context # Activities
15713379 10.1016/j.bmcl.2005.01.024 Unchecked 4
26638045 10.1016/j.ejmech.2015.11.019 Elastase 2
26638045 10.1016/j.ejmech.2015.11.019 Thermolysin 2
15713379 10.1016/j.bmcl.2005.01.024 Matrilysin 2
19775099 10.1021/jm900335a 72 kDa type IV collagenase 1
26263024 10.1021/acs.jmedchem.5b00367 U-87 MG 1
19775099 10.1021/jm900335a Matrix metalloproteinase-16 1
26638045 10.1016/j.ejmech.2015.11.019 Disintegrin and metalloproteinase domain-containing protein 17 1
19775099 10.1021/jm900335a Collagenase 3 1
19775099 10.1021/jm900335a Macrophage metalloelastase 1
19775099 10.1021/jm900335a Matrix metalloproteinase-9 1
19775099 10.1021/jm900335a Neutrophil collagenase 1
19775099 10.1021/jm900335a Stromelysin-1 1
15713379 10.1016/j.bmcl.2005.01.024 Interstitial collagenase 1
19775099 10.1021/jm900335a Interstitial collagenase 1
15713379 10.1016/j.bmcl.2005.01.024 Neutrophil collagenase 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
15713379 10.1016/j.bmcl.2005.01.024 Matrix metalloproteinase (2 and 3) 1
15713379 10.1016/j.bmcl.2005.01.024 Matrix metalloproteinase-14 1

Data from ChEMBL 36 via Core Engine