compound 68 [PMID: 24900699]   Click here for help

GtoPdb Ligand ID: 8165

Compound class: Synthetic organic
Comment: Compound 68 is a small molecule reported as a novel, potent inhibitor of the dual-specificity tyrosine-phosphorylation regulated kinases 1A and 1B [4].
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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.

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View interactive charts of activity data across species
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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Click here for structure editor
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 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 112.02
Molecular weight 430.99
XLogP 3.87
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(=N)c1nc2c(s1)c1c(ncnc1cc2)Nc1ccc(cc1F)Br
Isomeric SMILES COC(=N)c1nc2c(s1)c1c(ncnc1cc2)Nc1ccc(cc1F)Br
InChI InChI=1S/C17H11BrFN5OS/c1-25-15(20)17-24-12-5-4-11-13(14(12)26-17)16(22-7-21-11)23-10-3-2-8(18)6-9(10)19/h2-7,20H,1H3,(H,21,22,23)
InChI Key ZBELDPMWYXDLNY-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. Ferrer I, Barrachina M, Puig B, Martínez de Lagrán M, Martí E, Avila J, Dierssen M. (2005)
Constitutive Dyrk1A is abnormally expressed in Alzheimer disease, Down syndrome, Pick disease, and related transgenic models.
Neurobiol Dis, 20 (2): 392-400. [PMID:16242644]
2. Kimura R, Kamino K, Yamamoto M, Nuripa A, Kida T, Kazui H, Hashimoto R, Tanaka T, Kudo T, Yamagata H et al.. (2007)
The DYRK1A gene, encoded in chromosome 21 Down syndrome critical region, bridges between beta-amyloid production and tau phosphorylation in Alzheimer disease.
Hum Mol Genet, 16 (1): 15-23. [PMID:17135279]
3. Park J, Song WJ, Chung KC. (2009)
Function and regulation of Dyrk1A: towards understanding Down syndrome.
Cell Mol Life Sci, 66 (20): 3235-40. [PMID:19685005]
4. Rosse G. (2013)
Tricyclic Pyrimidines As Inhibitors of DYRK1A/DYRK1B As Potential Treatment for Down's Syndrome or Alzheimer's Disease.
ACS Med Chem Lett, 4 (6): 502-3. [PMID:24900699]
5. Ryoo SR, Jeong HK, Radnaabazar C, Yoo JJ, Cho HJ, Lee HW, Kim IS, Cheon YH, Ahn YS, Chung SH et al.. (2007)
DYRK1A-mediated hyperphosphorylation of Tau. A functional link between Down syndrome and Alzheimer disease.
J Biol Chem, 282 (48): 34850-7. [PMID:17906291]