izencitinib   Click here for help

GtoPdb Ligand ID: 10458

Synonyms: example 1 [WO2016191524A1] | JNJ-8398 | JNJ8398 | TD-1473 | TD1473
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Izencitinib (TD-1473) is described as a Janus kinase (JAK) inhibitor in INN proposed list 121 (of August 2019). It is example 1 in Theravance Biopharma's patent that claims JAK inhibitors for immunomodulatory potential [1]. Despite this 2020 article that describes preclinical development and early clinical evaluation of TD-1473 [2], the chemical structure remains undisclosed. TD-1473 is orally delivered, and was designed to be gut-selective in its action, for application in inflammatory bowel diseases.
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
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 7
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 105.55
Molecular weight 402.23
XLogP 3.15
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 N#CCCN1C2CCC1CC(C2)Nc1nc(Nc2n[nH]c(c2)C)cc2c1cccn2
Isomeric SMILES N#CCCN1[C@@H]2CC[C@H]1CC(C2)Nc1nc(Nc2n[nH]c(c2)C)cc2c1cccn2
InChI InChI=1S/C22H26N8/c1-14-10-21(29-28-14)26-20-13-19-18(4-2-8-24-19)22(27-20)25-15-11-16-5-6-17(12-15)30(16)9-3-7-23/h2,4,8,10,13,15-17H,3,5-6,9,11-12H2,1H3,(H3,25,26,27,28,29)/t15?,16-,17+
InChI Key DADAEARVGOQWHV-ALOPSCKCSA-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. Hudson R, Kozak J, Fatheree PR, Podesto DD, Brandt GEL, Fleury M, Beausoleil A-M, Huang X, Thalladi VR. (2016)
Naphthyridine compounds as jak kinase inhibitors.
Patent number: WO2016191524A1. Assignee: Theravance Biopharma R&D. Priority date: 28/05/2015. Publication date: 01/12/2016.
2. Sandborn WJ, Nguyen DD, Beattie DT, Brassil P, Krey W, Woo J, Situ E, Sana R, Sandvik E, Pulido-Rios MT et al.. (2020)
Development of Gut-Selective Pan-Janus Kinase Inhibitor TD-1473 for Ulcerative Colitis: A Translational Medicine Programme.
J Crohns Colitis, 14 (9): 1202-1213. [PMID:32161949]