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/)
References
1. Bloom J, Metz C, Nalawade S, Casabar J, Cheng KF, He M, Sherry B, Coleman T, Forsthuber T, Al-Abed Y. (2016)
Identification of Iguratimod as an Inhibitor of Macrophage Migration Inhibitory Factor (MIF) with Steroid-sparing Potential.
J Biol Chem, 291 (51): 26502-26514. [PMID:27793992]
2. Cisneros JA, Robertson MJ, Valhondo M, Jorgensen WL. (2016)
Irregularities in enzyme assays: The case of macrophage migration inhibitory factor.
Bioorg Med Chem Lett, 26 (12): 2764-2767. [PMID:27156768]
3. Lubetsky JB, Dios A, Han J, Aljabari B, Ruzsicska B, Mitchell R, Lolis E, Al-Abed Y. (2002)
The tautomerase active site of macrophage migration inhibitory factor is a potential target for discovery of novel anti-inflammatory agents.
J Biol Chem, 277 (28): 24976-82. [PMID:11997397]
4. Vujicic M, Nikolic I, Krajnovic T, Cheng KF, VanPatten S, He M, Stosic-Grujicic S, Stojanovic I, Al-Abed Y, Saksida T. (2014)
Novel inhibitors of macrophage migration inhibitory factor prevent cytokine-induced beta cell death.
Eur J Pharmacol, 740: 683-9. [PMID:24967533]
5. Zapatero MC, Pérez P, Vázquez MJ, Colmenarejo G, de Los Frailes M, Ramón F. (2016)
Discovery of Novel Inhibitors of the Tautomerase Activity of Macrophage Migration Inhibitory Factor (MIF).
J Biomol Screen, 21 (5): 446-58. [PMID:26933127]