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Compound Detail

CHEMBL44383

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COc1ccc(-c2ccc(S(=O)(=O)N[C@H](C(=O)O)C(C)C)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL44383
Phase Preclinical
Structure Type MOL
InChI Key MDWFJTBWOFNAQX-KRWDZBQOSA-N
7
Targets
19
Activities
1
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

363.4
MW (Da)
2.75
ALogP
4
HBA
2
HBD
92.7
PSA (Ų)
0.79
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 C18H21NO5S
MW 363.44
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.73

Activity Summary

IC50 19 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
72 kDa type IV collagenase
CHEMBL333
 IC50 8.52 8.4067 3.0 3
Collagenase 3
CHEMBL280
 IC50 8.22 8.02 6.0 3
Stromelysin-1
CHEMBL283
 IC50 8.1 7.3067 8.0 3
Neutrophil collagenase
CHEMBL4588
 IC50 7.97 7.97 10.6 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.13 5.7775 747.0 4
Interstitial collagenase
CHEMBL332
 IC50 5.82 5.5667 1500.0 3
Matrilysin
CHEMBL4073
 IC50 5.14 5.14 7200.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 2790.0 ng.hr.mL-1 Rattus norvegicus
AUC 2980.0 ng.hr.mL-1 Rattus norvegicus
Cmax 11721.33 nM -
T1/2 0.357 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase IC50 = 3.0 nM 8.52 Inhibition of matrix metalloprotease-2 12798337
72 kDa type IV collagenase IC50 = 3.0 nM 8.52 In vitro inhibition of matrix metalloprotease-2 (MMP-2) 10649971
Collagenase 3 IC50 = 6.0 nM 8.22 In vitro inhibition of human recombinant matrix metalloprotease-13 (MMP-13) 10649971
Collagenase 3 IC50 = 6.0 nM 8.22 Inhibition of human matrix metalloprotease-13 12798337
72 kDa type IV collagenase IC50 = 6.6 nM 8.18 In vitro inhibitory activity against matrix metalloprotease-2 11472202
Stromelysin-1 IC50 = 8.0 nM 8.1 In vitro inhibition of recombinant human matrix metalloprotease-3 (MMP-3) 10649971
Stromelysin-1 IC50 = 8.0 nM 8.1 Inhibition of matrix metalloprotease-3 12798337
Neutrophil collagenase IC50 = 10.6 nM 7.97 Inhibitory activity against matrix metalloprotease-8 11472202
Collagenase 3 IC50 = 24.2 nM 7.62 In vitro inhibitory activity against matrix metalloprotease-13 11472202
Matrix metalloproteinase-9 IC50 = 747.0 nM 6.13 In vitro inhibition of human matrix metalloprotease-9 11472202
Interstitial collagenase IC50 = 1500.0 nM 5.82 In vitro inhibition of human recombinant matrix metalloprotease-1 (MMP-1) 10649971
Interstitial collagenase IC50 = 1500.0 nM 5.82 Inhibition of matrix metalloprotease-1 12798337
Stromelysin-1 IC50 = 1890.0 nM 5.72 In vitro inhibitory activity against matrix metalloprotease-3 11472202
Matrix metalloproteinase-9 IC50 = 2200.0 nM 5.66 In vitro inhibition of matrix metalloprotease-9 (MMP-9) 10649971
Matrix metalloproteinase-9 IC50 = 2200.0 nM 5.66 Inhibition of matrix metalloprotease-9 12798337
Matrix metalloproteinase-9 IC50 = 2187.76 nM 5.66 Inhibition of MMP9 17275314
Matrilysin IC50 = 7200.0 nM 5.14 In vitro inhibition of matrix metalloprotease-7 (MMP-7) 10649971
Matrilysin IC50 = 7200.0 nM 5.14 Inhibition of matrix metalloprotease-7 12798337
Interstitial collagenase IC50 = 8710.0 nM 5.06 In vitro inhibitory activity against matrix metalloprotease-1 11472202

Literature References

PubMed DOI Target Context # Activities
10649971 10.1021/jm9903141 Rattus norvegicus 5
12798337 10.1016/s0960-894x(03)00382-2 Collagenase 3 2
11472202 10.1021/jm015531s Stromelysin-1 1
17275314 10.1016/j.bmc.2007.01.011 Matrix metalloproteinase-9 1
12798337 10.1016/s0960-894x(03)00382-2 Matrilysin 1
12798337 10.1016/s0960-894x(03)00382-2 Stromelysin-1 1
12798337 10.1016/s0960-894x(03)00382-2 72 kDa type IV collagenase 1
12798337 10.1016/s0960-894x(03)00382-2 Interstitial collagenase 1
11472202 10.1021/jm015531s Collagenase 3 1
11472202 10.1021/jm015531s Matrix metalloproteinase-9 1
11472202 10.1021/jm015531s Neutrophil collagenase 1
11472202 10.1021/jm015531s Matrilysin 1
10649971 10.1021/jm9903141 Interstitial collagenase 1
11472202 10.1021/jm015531s 72 kDa type IV collagenase 1
11472202 10.1021/jm015531s Interstitial collagenase 1
10649971 10.1021/jm9903141 ADMET 1
10649971 10.1021/jm9903141 Collagenase 3 1
10649971 10.1021/jm9903141 Matrix metalloproteinase-9 1
10649971 10.1021/jm9903141 Matrilysin 1
10649971 10.1021/jm9903141 Stromelysin-1 1

Data from ChEMBL 36 via Core Engine