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Compound Detail

CHEMBL4437091

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CCCCCc1ccc(C#Cc2ccc(C(=O)N3C[C@H](O)C[C@H]3C(=O)NO)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4437091
Phase Preclinical
Structure Type MOL
InChI Key HMXFQXRHTFBPFX-PKTZIBPZSA-N
5
Targets
6
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

420.5
MW (Da)
2.90
ALogP
4
HBA
3
HBD
89.9
PSA (Ų)
0.29
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H28N2O4
MW 420.51
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness -0.43

Activity Summary

IC50 5 meas. best 7.96
Ki 1 meas. best 6.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Collagenase 3
CHEMBL280
 IC50 7.96 7.96 11.0 1
72 kDa type IV collagenase
CHEMBL333
 IC50 6.82 6.82 151.0 1
Neutrophil collagenase
CHEMBL4588
 IC50 6.55 6.55 282.0 1
Unchecked
CHEMBL612545
 Ki 6.09 6.09 810.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.07 6.07 845.0 1
Unchecked
CHEMBL612545
 IC50 5.23 5.23 5900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Collagenase 3 IC50 = 11.0 nM 7.96 Inhibition of human MMP13 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(... 30954331
72 kDa type IV collagenase IC50 = 151.0 nM 6.82 Inhibition of human MMP2 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3... 30954331
Neutrophil collagenase IC50 = 282.0 nM 6.55 Inhibition of human MMP8 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3... 30954331
Unchecked Ki = 810.0 nM 6.09 Inhibition of Escherichia coli LpxC C63A mutant using UDP-3-O-[(R)-3-hydroxymyri... 30954331
Matrix metalloproteinase-9 IC50 = 845.0 nM 6.07 Inhibition of human MMP9 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3... 30954331
Unchecked IC50 = 5900.0 nM 5.23 Inhibition of Escherichia coli LpxC C63A mutant using UDP-3-O-[(R)-3-hydroxymyri... 30954331

Literature References

PubMed DOI Target Context # Activities
30954331 10.1016/j.bmc.2019.03.056 Escherichia coli 4
30954331 10.1016/j.bmc.2019.03.056 Unchecked 2
30954331 10.1016/j.bmc.2019.03.056 Klebsiella pneumoniae 1
30954331 10.1016/j.bmc.2019.03.056 Klebsiella oxytoca 1
30954331 10.1016/j.bmc.2019.03.056 Enterobacter cloacae 1
30954331 10.1016/j.bmc.2019.03.056 Klebsiella aerogenes 1
30954331 10.1016/j.bmc.2019.03.056 Proteus mirabilis 1
30954331 10.1016/j.bmc.2019.03.056 Proteus vulgaris 1
30954331 10.1016/j.bmc.2019.03.056 Citrobacter freundii 1
30954331 10.1016/j.bmc.2019.03.056 Pseudomonas aeruginosa 1
30954331 10.1016/j.bmc.2019.03.056 72 kDa type IV collagenase 1
30954331 10.1016/j.bmc.2019.03.056 Neutrophil collagenase 1
30954331 10.1016/j.bmc.2019.03.056 Matrix metalloproteinase-9 1
30954331 10.1016/j.bmc.2019.03.056 Collagenase 3 1

Data from ChEMBL 36 via Core Engine