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Compound Detail

CHEMBL38851

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N#Cc1ccc(-c2ccc(OCCC(=O)NO)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL38851
Phase Preclinical
Structure Type MOL
InChI Key XZWFHJUEAVOHHG-UHFFFAOYSA-N
6
Targets
11
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

282.3
MW (Da)
2.50
ALogP
4
HBA
2
HBD
82.3
PSA (Ų)
0.65
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H14N2O3
MW 282.30
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -1.04

Activity Summary

IC50 9 meas. best 7.6
Kd 2 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Stromelysin-1
CHEMBL283
 IC50 7.6 7.39 25.0 3
72 kDa type IV collagenase
CHEMBL333
 IC50 7.5 7.405 32.0 2
Rattus norvegicus
CHEMBL376
 IC50 7.24 7.24 57.0 1
Collagenase 3
CHEMBL280
 IC50 7.19 7.19 64.0 1
Stromelysin-1
CHEMBL283
 Kd 7.0 6.98 100.0 2
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.18 6.18 655.0 1
Interstitial collagenase
CHEMBL332
 IC50 5.48 5.48 3300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Stromelysin-1 IC50 = 25.0 nM 7.6 Inhibition of Matrix Metalloprotease-3 (MMP-3) 15214773
72 kDa type IV collagenase IC50 = 32.0 nM 7.5 In vitro inhibition of Matrix metalloprotease-2 11412979
Stromelysin-1 IC50 = 47.0 nM 7.33 Inhibition of Matrix metalloprotease-3 11212095
72 kDa type IV collagenase IC50 = 49.0 nM 7.31 Inhibition of Matrix metalloprotease-2 11212095
Rattus norvegicus IC50 = 57.0 nM 7.24 Bioavailability after peroral administration at 30 mg/kg against Stromelysin in ... 12477346
Stromelysin-1 IC50 = 57.0 nM 7.24 In vitro inhibition of Matrix metalloprotease-3 11412979
Collagenase 3 IC50 = 64.0 nM 7.19 Inhibition of Matrix metalloprotease-13 11212095
Stromelysin-1 Kd = 100.0 nM 7.0 Binding affinity to stromelysin-1 catalytic domain 19942433
Stromelysin-1 Kd = 110.0 nM 6.96 Binding affinity to stromelysin-1 catalytic domain expressed in Escherichia coli... 19942433
Matrix metalloproteinase-9 IC50 = 655.0 nM 6.18 Inhibition of Matrix metalloprotease-9 11212095
Interstitial collagenase IC50 = 3300.0 nM 5.48 In vitro inhibition of Matrix metalloprotease-1. 11412979

Literature References

PubMed DOI Target Context # Activities
19942433 10.1016/j.bmcl.2009.10.114 Stromelysin-1 2
15214773 10.1021/jm040031v Stromelysin-1 1
11212095 10.1016/s0960-894x(00)00646-6 Interstitial collagenase 1
11212095 10.1016/s0960-894x(00)00646-6 72 kDa type IV collagenase 1
11212095 10.1016/s0960-894x(00)00646-6 Stromelysin-1 1
11212095 10.1016/s0960-894x(00)00646-6 Matrix metalloproteinase-9 1
11212095 10.1016/s0960-894x(00)00646-6 Collagenase 3 1
12477346 10.1021/jm020160g Rattus norvegicus 1
11412979 10.1016/s0960-894x(01)00031-2 72 kDa type IV collagenase 1
11412979 10.1016/s0960-894x(01)00031-2 Stromelysin-1 1
11412979 10.1016/s0960-894x(01)00031-2 Interstitial collagenase 1

Data from ChEMBL 36 via Core Engine