birelentinib   Click here for help

GtoPdb Ligand ID: 13735

Synonyms: compound 14 [WO2021136219A1] | DZD-8586 | DZD8586
Compound class: Synthetic organic
Comment: The chemical structure for birelentinib was derived from WHO proposed INN list 132 (Feb 2025), in which it is listed as a tyrosine kinase inhibitor with antineoplastic potential. It is one of the structures claimed as BTK inhibitors in patent WO2021136219A1 (Dizal Pharmaceutical Co.) [1]. Analysis of Dizal Pharmaceuticals' pipeline suggests that birelentinib may be the INN for their lead dual LYN/BTK inhibitor DZD8586 that is designed to inhbit B-cell antigen receptor (BCR) signalling pathways in B cell malignancies, although at time of writing no name to structure had been formally disclosed (Feb 2025). It is impossible to tell from the patent if birelentinib is compound 14 or compound 15 as the absolute stereochemistry is unclear, although 14 is more probable as it more potently inhibits BTK activity in vitro. DZD8586 is a non-covalent inhibitor that can penetrate the blood-brain barrier.
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 8
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 105.03
Molecular weight 453.44
XLogP 0.52
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 C1=CC(=C(C(=C1)F)F)OC2=CC=C(C=C2)C3=C4C(=NC=NN4C(=N3)[C@@H]5CC[C@@H](CO)OC5)N
Isomeric SMILES NC1=NC=NN2C1=C(N=C2[C@@H]3CC[C@H](OC3)CO)C4=CC=C(C=C4)OC5=C(C(=CC=C5)F)F
InChI InChI=1S/C23H21F2N5O3/c24-17-2-1-3-18(19(17)25)33-15-7-4-13(5-8-15)20-21-22(26)27-12-28-30(21)23(29-20)14-6-9-16(10-31)32-11-14/h1-5,7-8,12,14,16,31H,6,9-11H2,(H2,26,27,28)/t14-,16+/m1/s1
InChI Key NQJKXHPWHYRGST-ZBFHGGJFSA-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. Zhou Q, Shen C, Chen X, Liu W, WAng R, Zeng Q, Tsui H, Yang Z, Zhang X. (2021)
Btk inhibitors.
Patent number: WO2021136219A1. Assignee: Dizal (Jiangsu) Pharmaceutical Co., Ltd.. Priority date: 29/12/2020. Publication date: 08/07/2021.