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.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

ilomastat is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
MMP13 Hs Inhibitor Inhibition 9.6 pIC50 - 4
⤷ pIC50 9.6 (IC50 2.8x10-10 M) [4]
ADAM9 Hs Inhibitor Inhibition 9.0 pIC50 - 3
⤷ pIC50 9.0 (IC50 1x10-9 M) [3]
Description: Measured in an in vitro assay.
MMP8 Hs Inhibitor Inhibition 9.0 pIC50 - 4
⤷ pIC50 9.0 (IC50 1.1x10-9 M) [4]
MMP2 Hs Inhibitor Inhibition 8.1 – 9.7 pIC50 - 2,4
⤷ pIC50 9.7 (IC50 1.9x10-10 M) [4]
pIC50 8.1 (IC50 7x10-9 M) [2]
MMP1 Hs Inhibitor Inhibition 8.2 – 9.3 pIC50 - 2,4
⤷ pIC50 9.3 (IC50 5.6x10-10 M) [4]
pIC50 8.2 (IC50 6x10-9 M) [2]
MMP12 Hs Inhibitor Inhibition 7.9 – 9.3 pIC50 - 2,4
⤷ pIC50 9.3 (IC50 4.6x10-10 M) [4]
pIC50 7.9 (IC50 1.3x10-8 M) [2]
MMP17 Hs Inhibitor Inhibition 8.5 pIC50 - 1
⤷ pIC50 8.5 (IC50 3.4x10-9 M) [1]
MMP9 Hs Inhibitor Inhibition 7.8 – 9.0 pIC50 - 2,4
⤷ pIC50 9.0 (IC50 9.3x10-10 M) [4]
pIC50 7.8 (IC50 1.5x10-8 M) [2]
MMP14 Hs Inhibitor Inhibition 7.6 – 9.0 pIC50 - 2,4
⤷ pIC50 9.0 (IC50 1.1x10-9 M) [4]
pIC50 7.6 (IC50 2.3x10-8 M) [2]
MMP7 Hs Inhibitor Inhibition 8.3 pIC50 - 4
⤷ pIC50 8.3 (IC50 5.1x10-9 M) [4]
ADAM12 Hs Inhibitor Inhibition 8.2 pIC50 - 3
⤷ pIC50 8.2 (IC50 5.93x10-9 M) [3]
Description: Measured in a cell-based assay.
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.
MMP26 Hs Inhibitor Inhibition 7.8 pIC50 - 2
⤷ pIC50 7.8 (IC50 1.7x10-8 M) [2]
MMP3 Hs Inhibitor Inhibition 7.5 pIC50 - 4
⤷ pIC50 7.5 (IC50 3.2x10-8 M) [4]