Cdk4 inhibitor III   Click here for help

GtoPdb Ligand ID: 5952

Synonyms: ryuvidine
Compound class: Synthetic organic
Comment: CDK4 inhibitor III (ryuvidine), as its name suggests was originally reported as a selective inhibitor of CDK4, albeit a weak inhibitor [6]. However, to date (October 2018) there is no published data showing cellular inhibition of CDK4 by this compound, but some evidence of action at another target(s) that regulates the S phase of the cell cycle has been reported [5]. This latter effect may be due to CDK4 inhibitor III-induced inhibition of the lysine methyltransferase SETD8 [2,4].
Click here for help

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.

✖

View interactive charts of activity data across species

Cdk4 inhibitor III 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 CDK toolkit. 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 1
Rotatable bonds 2
Topological polar surface area 87.3
Molecular weight 284.06
XLogP 2.2
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES Cc1ccc(cc1)NC1=CC(=O)c2c(C1=O)nc(s2)C
Isomeric SMILES Cc1ccc(cc1)NC1=CC(=O)c2c(C1=O)nc(s2)C
InChI InChI=1S/C15H12N2O2S/c1-8-3-5-10(6-4-8)17-11-7-12(18)15-13(14(11)19)16-9(2)20-15/h3-7,17H,1-2H3
InChI Key HFPLHASLIOXVGS-UHFFFAOYSA-N
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. Blum G, Ibáñez G, Rao X, Shum D, Radu C, Djaballah H, Rice JC, Luo M. (2014)
Small-molecule inhibitors of SETD8 with cellular activity.
ACS Chem Biol, 9 (11): 2471-8. [PMID:25137013]
3. 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]
4. Houston SI, McManus KJ, Adams MM, Sims JK, Carpenter PB, Hendzel MJ, Rice JC. (2008)
Catalytic function of the PR-Set7 histone H4 lysine 20 monomethyltransferase is essential for mitotic entry and genomic stability.
J Biol Chem, 283 (28): 19478-88. [PMID:18480059]
5. Jorda R, Hendrychová D, Voller J, Řezníčková E, Gucký T, Kryštof V. (2018)
How Selective Are Pharmacological Inhibitors of Cell-Cycle-Regulating Cyclin-Dependent Kinases?.
J Med Chem, 61 (20): 9105-9120. [PMID:30234987]
6. Ryu CK, Kang HY, Lee SK, Nam KA, Hong CY, Ko WG, Lee BH. (2000)
5-Arylamino-2-methyl-4,7-dioxobenzothiazoles as inhibitors of cyclin-dependent kinase 4 and cytotoxic agents.
Bioorg Med Chem Lett, 10 (5): 461-4. [PMID:10743948]