ilomastat   Click here for help

GtoPdb Ligand ID: 7409

Synonyms: CS 610 | GM 6001
PDB Ligand
Compound class: Synthetic organic
Comment: Ilomastat is a broad-spectrum inhibitor of group M10 and M12 metallopeptidases.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 5
Rotatable bonds 12
Topological polar surface area 123.32
Molecular weight 388.21
XLogP 1.62
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES ONC(=O)CC(C(=O)NC(C(=O)NC)Cc1c[nH]c2c1cccc2)CC(C)C
Isomeric SMILES ONC(=O)C[C@H](C(=O)N[C@H](C(=O)NC)Cc1c[nH]c2c1cccc2)CC(C)C
InChI InChI=1S/C20H28N4O4/c1-12(2)8-13(10-18(25)24-28)19(26)23-17(20(27)21-3)9-14-11-22-16-7-5-4-6-15(14)16/h4-7,11-13,17,22,28H,8-10H2,1-3H3,(H,21,27)(H,23,26)(H,24,25)/t13-,17+/m1/s1
InChI Key NITYDPDXAAFEIT-DYVFJYSZSA-N
Bioactivity Comments
We have mapped ilomastat (galardin) data from [2] to human MMPs, although species is not specified in the Methods section of the article.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
ADAM9 Hs Inhibitor Inhibition 9.0 pIC50 - 3
pIC50 9.0 (IC50 1x10-9 M) [3]
Description: Measured in an in vitro assay.
MMP17 Hs Inhibitor Inhibition 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.4x10-9 M) [1]
ADAM12 Hs Inhibitor Inhibition 8.2 pIC50 - 3
pIC50 8.2 (IC50 5.93x10-9 M) [3]
Description: Measured in a cell-based assay.
MMP1 Hs Inhibitor Inhibition 8.2 pIC50 - 2
pIC50 8.2 (IC50 6x10-9 M) [2]
MMP2 Hs Inhibitor Inhibition 8.1 pIC50 - 2
pIC50 8.1 (IC50 7x10-9 M) [2]
ADAM17 Hs Inhibitor Inhibition 8.1 pIC50 - 3
pIC50 8.1 (IC50 7.5x10-9 M) [3]
Description: Measured in an in vitro assay.
MMP15 Hs Inhibitor Inhibition 8.1 pIC50 - 2
pIC50 8.1 (IC50 8x10-9 M) [2]
MMP16 Hs Inhibitor Inhibition 8.1 pIC50 - 2
pIC50 8.1 (IC50 8x10-9 M) [2]
ADAM10 Hs Inhibitor Inhibition 8.1 pIC50 - 3
pIC50 8.1 (IC50 8.1x10-9 M) [3]
Description: Measured in an in vitro assay.
MMP12 Hs Inhibitor Inhibition 7.9 pIC50 - 2
pIC50 7.9 (IC50 1.3x10-8 M) [2]
MMP9 Hs Inhibitor Inhibition 7.8 pIC50 - 2
pIC50 7.8 (IC50 1.5x10-8 M) [2]
MMP26 Hs Inhibitor Inhibition 7.8 pIC50 - 2
pIC50 7.8 (IC50 1.7x10-8 M) [2]
MMP14 Hs Inhibitor Inhibition 7.6 pIC50 - 2
pIC50 7.6 (IC50 2.3x10-8 M) [2]