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Compound Detail

CHEMBL24398

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O=C(NO)[C@@H](NCC1CC1)[C@@H](Cc1cccc(O)c1)C(=O)N[C@H]1c2ccccc2C[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL24398
Phase Preclinical
Structure Type MOL
InChI Key UACUZULRKJKTHE-CZYKHXBRSA-N
8
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

439.5
MW (Da)
1.20
ALogP
6
HBA
6
HBD
130.9
PSA (Ų)
0.26
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 C24H29N3O5
MW 439.51
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness 0.43

Activity Summary

Ki 12 meas. best 6.77
IC50 10 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A disintegrin and metalloproteinase with thrombospondin motifs 4
CHEMBL2318
 IC50 8.52 8.52 3.0 3
A disintegrin and metalloproteinase with thrombospondin motifs 5
CHEMBL2285
 IC50 7.92 7.82 12.0 3
Unchecked
CHEMBL612545
 IC50 7.92 7.92 12.0 3
Neutrophil collagenase
CHEMBL4588
 Ki 6.77 6.6767 171.0 3
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 6.37 6.37 430.0 1
Matrix metalloproteinase-9
CHEMBL321
 Ki 5.9 5.4875 1261.0 4
72 kDa type IV collagenase
CHEMBL333
 Ki 5.3 5.2333 4995.0 3
Interstitial collagenase
CHEMBL332
 Ki 4.48 4.48 33160.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 3.0 nM 8.52 Inhibition of human recombinant ADAMTS4 expressed in HEk293 cells using FAM-AEwL... 23376997
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 3.0 nM 8.52 Inhibition of recombinant human ADAMTS-4 36250680
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 3.0 nM 8.52 Inhibition of human recombinant aggrecanase 1 after 150 mins by fluorescence pla... 21417219
Unchecked IC50 = 12.0 nM 7.92 Inhibition of bovine aggrecanase 12657268
Unchecked IC50 = 12.0 nM 7.92 Inhibition of aggrecanase 11585439
Unchecked IC50 = 12.0 nM 7.92 Inhibition of bovine aggrecanase 18790648
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 12.0 nM 7.92 Inhibition of human recombinant aggrecanase 2 after 150 mins by fluorescence pla... 21417219
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 17.0 nM 7.77 Inhibition of human recombinant ADAMTS5 expressed in HEK293 cells using Abz-TESE... 23376997
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 17.0 nM 7.77 Inhibition of recombinant human ADAMTS-5 36250680
Neutrophil collagenase Ki = 171.0 nM 6.77 Inhibition of MMP8 18790648
Neutrophil collagenase Ki = 171.0 nM 6.77 Inhibition of matrix metalloprotease-8 11585439
Neutrophil collagenase Ki = 321.0 nM 6.49 Inhibition of MMP8 (unknown origin) 36250680
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 430.0 nM 6.37 Inhibition of human recombinant TACE after 60 mins by fluorescence plate reader 21417219
Matrix metalloproteinase-9 Ki = 1261.0 nM 5.9 Inhibition of MMP9 (unknown origin) 36250680
Matrix metalloproteinase-9 Ki = 4468.0 nM 5.35 Affinity for Matrix metalloprotease-9 (MMP-9) 12657268
Matrix metalloproteinase-9 Ki = 4468.0 nM 5.35 Inhibition of human matrix metalloprotease-9 11585439
Matrix metalloproteinase-9 Ki = 4468.0 nM 5.35 Inhibition of MMP9 18790648
72 kDa type IV collagenase Ki = 4995.0 nM 5.3 Inhibition of MMP2 (unknown origin) 36250680
72 kDa type IV collagenase Ki = 6300.0 nM 5.2 Inhibition of matrix metalloprotease-2 11585439
72 kDa type IV collagenase Ki = 6300.0 nM 5.2 Inhibition of MMP2 18790648

Literature References

PubMed DOI Target Context # Activities
18790648 10.1016/j.bmc.2008.08.058 Matrix metalloproteinase-9 1
36250680 10.1021/acs.jmedchem.2c01177 Matrix metalloproteinase-9 1
36250680 10.1021/acs.jmedchem.2c01177 A disintegrin and metalloproteinase with thrombospondin motifs 4 1
23376997 10.1016/j.ejmech.2012.12.058 A disintegrin and metalloproteinase with thrombospondin motifs 5 1
23376997 10.1016/j.ejmech.2012.12.058 A disintegrin and metalloproteinase with thrombospondin motifs 4 1
21417219 10.1021/jm101609j Disintegrin and metalloproteinase domain-containing protein 17 1
21417219 10.1021/jm101609j Interstitial collagenase 1
21417219 10.1021/jm101609j Matrix metalloproteinase-14 1
21417219 10.1021/jm101609j A disintegrin and metalloproteinase with thrombospondin motifs 5 1
21417219 10.1021/jm101609j A disintegrin and metalloproteinase with thrombospondin motifs 4 1
18790648 10.1016/j.bmc.2008.08.058 Unchecked 1
12657268 10.1016/s0960-894x(03)00124-0 Unchecked 1
18790648 10.1016/j.bmc.2008.08.058 Neutrophil collagenase 1
18790648 10.1016/j.bmc.2008.08.058 72 kDa type IV collagenase 1
18790648 10.1016/j.bmc.2008.08.058 Interstitial collagenase 1
11585439 10.1021/jm015533c Matrix metalloproteinase-9 1
11585439 10.1021/jm015533c 72 kDa type IV collagenase 1
11585439 10.1021/jm015533c Interstitial collagenase 1
11585439 10.1021/jm015533c Neutrophil collagenase 1
11585439 10.1021/jm015533c Unchecked 1

Data from ChEMBL 36 via Core Engine