PD166285   Click here for help

GtoPdb Ligand ID: 8183

Synonyms: PD-166285 | PD0166285 [5]
PDB Ligand
Compound class: Synthetic organic
Comment: PD166285 was originally reported as a tyrosine kinase inhibitor [1-2,4], and has subsequently been identified as an inhibitor of Wee1 [5] and Myt1 (PKMYT1) [3], two cyclin-dependent kinase (CDK) inhibitory kinases involved in regulating the cell cycle.
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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

PD166285 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 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 72.28
Molecular weight 511.15
XLogP 6.53
No. Lipinski's rules broken 1

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 CCN(CCOc1ccc(cc1)Nc1ncc2c(n1)n(C)c(=O)c(c2)c1c(Cl)cccc1Cl)CC
Isomeric SMILES CCN(CCOc1ccc(cc1)Nc1ncc2c(n1)n(C)c(=O)c(c2)c1c(Cl)cccc1Cl)CC
InChI InChI=1S/C26H27Cl2N5O2/c1-4-33(5-2)13-14-35-19-11-9-18(10-12-19)30-26-29-16-17-15-20(25(34)32(3)24(17)31-26)23-21(27)7-6-8-22(23)28/h6-12,15-16H,4-5,13-14H2,1-3H3,(H,29,30,31)
InChI Key IFPPYSWJNWHOLQ-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. Klutchko SR, Hamby JM, Boschelli DH, Wu Z, Kraker AJ, Amar AM, Hartl BG, Shen C, Klohs WD, Steinkampf RW et al.. (1998)
2-Substituted aminopyrido[2,3-d]pyrimidin-7(8H)-ones. structure-activity relationships against selected tyrosine kinases and in vitro and in vivo anticancer activity.
J Med Chem, 41 (17): 3276-92. [PMID:9703473]
2. Panek RL, Lu GH, Klutchko SR, Batley BL, Dahring TK, Hamby JM, Hallak H, Doherty AM, Keiser JA. (1997)
In vitro pharmacological characterization of PD 166285, a new nanomolar potent and broadly active protein tyrosine kinase inhibitor.
J Pharmacol Exp Ther, 283 (3): 1433-44. [PMID:9400019]
3. Rohe A, Erdmann F, Bäßler C, Wichapong K, Sippl W, Schmidt M. (2012)
In vitro and in silico studies on substrate recognition and acceptance of human PKMYT1, a Cdk1 inhibitory kinase.
Bioorg Med Chem Lett, 22 (2): 1219-23. [PMID:22189141]
4. Trumpp-Kallmeyer S, Rubin JR, Humblet C, Hamby JM, Showalter HD. (1998)
Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors.
J Med Chem, 41 (11): 1752-63. [PMID:9599227]
5. Wang Y, Li J, Booher RN, Kraker A, Lawrence T, Leopold WR, Sun Y. (2001)
Radiosensitization of p53 mutant cells by PD0166285, a novel G(2) checkpoint abrogator.
Cancer Res, 61 (22): 8211-7. [PMID:11719452]