CC-401   Click here for help

GtoPdb Ligand ID: 11457

Synonyms: CC401
Compound class: Synthetic organic
Comment: CC-401 was originally identified as a c-Jun N-terminal kinase (JNK) inhibitor. It was developed by Celgene who advanced it into clinical trial for anti-leukemia potential [3], but this programme was abandoned. CC-401 was subsequently found to inhibit DYRK1A and DYRK1B [1]. It promotes replication of pancreatic β-cells in vitro (rat and human) and in vivo (rat) via DYRK1A/B-dependent mechanisms.
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

CC-401 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 82.72
Molecular weight 388.2
XLogP 4.5
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 C1CCN(CC1)CCOc1cccc(c1)c1n[nH]c2c1cc(cc2)c1[nH]cnn1
Isomeric SMILES C1CCN(CC1)CCOc1cccc(c1)c1n[nH]c2c1cc(cc2)c1[nH]cnn1
InChI InChI=1S/C22H24N6O/c1-2-9-28(10-3-1)11-12-29-18-6-4-5-16(13-18)21-19-14-17(22-23-15-24-27-22)7-8-20(19)25-26-21/h4-8,13-15H,1-3,9-12H2,(H,25,26)(H,23,24,27)
InChI Key XDJCLCLBSGGNKS-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. Abdolazimi Y, Zhao Z, Lee S, Xu H, Allegretti P, Horton TM, Yeh B, Moeller HP, Nichols RJ, McCutcheon D et al.. (2018)
CC-401 Promotes β-Cell Replication via Pleiotropic Consequences of DYRK1A/B Inhibition.
Endocrinology, 159 (9): 3143-3157. [PMID:29514186]
2. Edupuganti R, Taliaferro JM, Wang Q, Xie X, Cho EJ, Vidhu F, Ren P, Anslyn EV, Bartholomeusz C, Dalby KN. (2017)
Discovery of a potent inhibitor of MELK that inhibits expression of the anti-apoptotic protein Mcl-1 and TNBC cell growth.
Bioorg Med Chem, 25 (9): 2609-2616. [PMID:28351607]
3. Han SY. (2008)
c-Jun N-Terminal Kinase Signaling Inhibitors Under Development.
Toxicol Res, 24 (2): 93-100. [PMID:32038782]