NF-kB activation inhibitor   Click here for help

GtoPdb Ligand ID: 6012

Synonyms: AG-F-89549 | EVP4593
Compound class: Synthetic organic
Comment: This compound potently inhibits nuclear factor-κB (NFκB) activation and LPS-induced TNFα production [7]. Its discovery is reported in [7] where it is compound 11q.

NF-kB activation inhibitor 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 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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 73.06
Molecular weight 356.16
XLogP 3.99
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
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.

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/)

✖
Canonical SMILES Nc1ccc2c(c1)c(NCCc1ccc(cc1)Oc1ccccc1)ncn2
Isomeric SMILES Nc1ccc2c(c1)c(NCCc1ccc(cc1)Oc1ccccc1)ncn2
InChI InChI=1S/C22H20N4O/c23-17-8-11-21-20(14-17)22(26-15-25-21)24-13-12-16-6-9-19(10-7-16)27-18-4-2-1-3-5-18/h1-11,14-15H,12-13,23H2,(H,24,25,26)
InChI Key IBAKVEUZKHOWNG-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. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1039-45. [PMID:22037377]
2. Baeuerle PA, Baltimore D. (1996)
NF-kappa B: ten years after.
Cell, 87 (1): 13-20. [PMID:8858144]
3. Baeuerle PA, Henkel T. (1994)
Function and activation of NF-kappa B in the immune system.
Annu Rev Immunol, 12: 141-79. [PMID:8011280]
4. Blackwell TS, Christman JW. (1997)
The role of nuclear factor-kappa B in cytokine gene regulation.
Am J Respir Cell Mol Biol, 17 (1): 3-9. [PMID:9224203]
5. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem J, 451 (2): 313-28. [PMID:23398362]
6. May MJ, Ghosh S. (1998)
Signal transduction through NF-kappa B.
Immunol Today, 19 (2): 80-8. [PMID:9509763]
7. Tobe M, Isobe Y, Tomizawa H, Nagasaki T, Takahashi H, Fukazawa T, Hayashi H. (2003)
Discovery of quinazolines as a novel structural class of potent inhibitors of NF-kappa B activation.
Bioorg Med Chem, 11 (3): 383-91. [PMID:12517433]
8. Vossen AC, Savelkoul HF. (1994)
Cytokines in clinical and experimental transplantation.
Mediators Inflamm, 3 (6): 403-10. [PMID:18475587]
9. Wu J, Shih HP, Vigont V, Hrdlicka L, Diggins L, Singh C, Mahoney M, Chesworth R, Shapiro G, Zimina O et al.. (2011)
Neuronal store-operated calcium entry pathway as a novel therapeutic target for Huntington's disease treatment.
Chem Biol, 18 (6): 777-93. [PMID:21700213]