ISO-1   Click here for help

GtoPdb Ligand ID: 9984

Synonyms: IN1228
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: ISO-1 is a prototypical inhibitor of the tautomerase activity of macrophage migration inhibitory factor (MIF) [3].

ISO-1 is commercially available from our sponsors

2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 64.63
Molecular weight 235.08
XLogP 0.15
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)CC1ONC(=C2C=CC(=O)C=C2)C1
Isomeric SMILES COC(=O)CC1ONC(=C2C=CC(=O)C=C2)C1
InChI InChI=1S/C12H13NO4/c1-16-12(15)7-10-6-11(13-17-10)8-2-4-9(14)5-3-8/h2-5,10,13H,6-7H2,1H3
InChI Key CLVQGFPQFNASJH-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Immunopharmacology Comments
ISO-1 inhibits the tautomerase activity of MIF. It should be used as a positive control in studies used to identify new MIF inhibitors. However, users should be aware of the variations in activity that can be observed when using this compund in tautomerase activity assay formats that utilise different substrates, i.e. D-dopachrome methyl ester (dopachrome) and p-hydroxyphenyl pyruvic acid (HPP) assays) [2].. Reported IC50s for ISO-1 lie in a wide range from 7-100 μM, but the consensus is that the value actually sits around 18 μM [1,4-5].