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Compound Detail

CHEMBL4208519

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Cc1cc(COc2ccc(S(=O)(=O)N(C)C3(C(=O)NO)CN(C(=O)CC(C)C)C3)cc2)c2ccccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4208519
Phase Preclinical
Structure Type MOL
InChI Key LZUHYMGQNXWOHQ-UHFFFAOYSA-N
12
Targets
16
Activities
1
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

540.6
MW (Da)
2.88
ALogP
7
HBA
2
HBD
129.1
PSA (Ų)
0.32
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H32N4O6S
MW 540.64
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness -1.00

Activity Summary

IC50 16 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Macrophage metalloelastase
CHEMBL4393
 IC50 8.22 8.22 6.0 1
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 8.15 7.8675 7.0 4
Stromelysin-1
CHEMBL283
 IC50 7.05 7.05 90.0 1
Matrilysin
CHEMBL4073
 IC50 6.68 6.68 210.0 1
Disintegrin and metalloproteinase domain-containing protein 9
CHEMBL5982
 IC50 6.32 6.32 480.0 1
72 kDa type IV collagenase
CHEMBL333
 IC50 6.0 6.0 1000.0 1
Collagenase 3
CHEMBL280
 IC50 5.92 5.92 1200.0 1
Disintegrin and metalloproteinase domain-containing protein 10
CHEMBL5028
 IC50 5.89 5.89 1300.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 5.66 5.66 2200.0 1
Neutrophil collagenase
CHEMBL4588
 IC50 5.43 5.43 3700.0 1
Matrix metalloproteinase-14
CHEMBL3869
 IC50 5.36 5.36 4400.0 1
Interstitial collagenase
CHEMBL332
 IC50 5.34 5.335 4600.0 2

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.003 - Homo sapiens
T1/2 24.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Macrophage metalloelastase IC50 = 6.0 nM 8.22 Inhibition of MMP12 (unknown origin) 28818461
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 7.0 nM 8.15 Inhibition of recombinant human TACE catalytic domain using Mca-Pro-Leu-Ala-Gln-... 28818461
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 7.2 nM 8.14 TR-FRET Assay: Activity of the compounds was investigated using TACE (ADAM17) is... -
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 20.0 nM 7.7 Inhibition of TACE in NHEK assessed as reduction in LPS/TPA-stimulated TNFalpha ... 28818461
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 33.0 nM 7.48 Inhibition of TACE in human PBMC assessed as reduction in LPS-induced TNFalpha p... 28818461
Stromelysin-1 IC50 = 90.0 nM 7.05 Inhibition of MMP3 (unknown origin) 28818461
Matrilysin IC50 = 210.0 nM 6.68 Inhibition of MMP7 (unknown origin) 28818461
Disintegrin and metalloproteinase domain-containing protein 9 IC50 = 480.0 nM 6.32 Inhibition of ADAM9 (unknown origin) 28818461
72 kDa type IV collagenase IC50 = 1000.0 nM 6.0 Inhibition of MMP2 (unknown origin) 28818461
Collagenase 3 IC50 = 1200.0 nM 5.92 Inhibition of MMP13 (unknown origin) 28818461
Disintegrin and metalloproteinase domain-containing protein 10 IC50 = 1300.0 nM 5.89 Inhibition of ADAM10 (unknown origin) 28818461
Matrix metalloproteinase-9 IC50 = 2200.0 nM 5.66 Inhibition of MMP9 (unknown origin) 28818461
Neutrophil collagenase IC50 = 3700.0 nM 5.43 Inhibition of MMP8 (unknown origin) 28818461
Matrix metalloproteinase-14 IC50 = 4400.0 nM 5.36 Inhibition of MMP14 (unknown origin) 28818461
Interstitial collagenase IC50 = 4600.0 nM 5.34 Inhibition of recombinant human MMP1 catalytic domain using Mca-Pro-Leu-Gly-Leu-... 28818461
Interstitial collagenase IC50 = 4625.0 nM 5.33 Inhibition Assay: The enzymatic reaction was performed in 384-well microplates w... -

Literature References

PubMed DOI Target Context # Activities
28818461 10.1016/j.bmc.2017.07.054 TK6 4
28818461 10.1016/j.bmc.2017.07.054 Salmonella typhimurium 4
28818461 10.1016/j.bmc.2017.07.054 No relevant target 3
28818461 10.1016/j.bmc.2017.07.054 Disintegrin and metalloproteinase domain-containing protein 17 3
28818461 10.1016/j.bmc.2017.07.054 Unchecked 2
28818461 10.1016/j.bmc.2017.07.054 Cytochrome P450 3A4 1
28818461 10.1016/j.bmc.2017.07.054 Voltage-gated inwardly rectifying potassium channel KCNH2 1
28818461 10.1016/j.bmc.2017.07.054 ADMET 1
28818461 10.1016/j.bmc.2017.07.054 Matrix metalloproteinase-14 1
28818461 10.1016/j.bmc.2017.07.054 Collagenase 3 1
28818461 10.1016/j.bmc.2017.07.054 Macrophage metalloelastase 1
28818461 10.1016/j.bmc.2017.07.054 Matrix metalloproteinase-9 1
28818461 10.1016/j.bmc.2017.07.054 Neutrophil collagenase 1
28818461 10.1016/j.bmc.2017.07.054 Matrilysin 1
28818461 10.1016/j.bmc.2017.07.054 Stromelysin-1 1
28818461 10.1016/j.bmc.2017.07.054 72 kDa type IV collagenase 1
28818461 10.1016/j.bmc.2017.07.054 Interstitial collagenase 1
28818461 10.1016/j.bmc.2017.07.054 Disintegrin and metalloproteinase domain-containing protein 10 1
28818461 10.1016/j.bmc.2017.07.054 Disintegrin and metalloproteinase domain-containing protein 9 1
28818461 10.1016/j.bmc.2017.07.054 Hepatocyte 1

Data from ChEMBL 36 via Core Engine