MIF inhibitor 3bb   Click here for help

GtoPdb Ligand ID: 9986

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 3bb is the most potent inhibitor of macrophage migration inhibitory factor (MIF) tautomerase activity identified from a SAR series by Dziedzic et al. (2015) [1]. It is referred to as quinoline 20 in [2].
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 5
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 109.84
Molecular weight 442.11
XLogP 4.52
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 OC(=O)c1cccc(c1)Oc1cccc2c1ccc(n2)c1nnn(c1)c1ccc(c(c1)F)O
Isomeric SMILES OC(=O)c1cccc(c1)Oc1cccc2c1ccc(n2)c1nnn(c1)c1ccc(c(c1)F)O
InChI InChI=1S/C24H15FN4O4/c25-18-12-15(7-10-22(18)30)29-13-21(27-28-29)20-9-8-17-19(26-20)5-2-6-23(17)33-16-4-1-3-14(11-16)24(31)32/h1-13,30H,(H,31,32)
InChI Key RXHQCISHMPQZDT-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. Dziedzic P, Cisneros JA, Robertson MJ, Hare AA, Danford NE, Baxter RH, Jorgensen WL. (2015)
Design, synthesis, and protein crystallography of biaryltriazoles as potent tautomerase inhibitors of macrophage migration inhibitory factor.
J Am Chem Soc, 137 (8): 2996-3003. [PMID:25697265]
2. Trivedi-Parmar V, Jorgensen WL. (2018)
Advances and Insights for Small Molecule Inhibition of Macrophage Migration Inhibitory Factor.
J Med Chem, 61 (18): 8104-8119. [PMID:29812929]