parsaclisib   Click here for help

GtoPdb Ligand ID: 10098

Synonyms: compound 20 [PMID: 31749910] | IBI376 | INCB-050465
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Parsaclisib (INCB050465) is a PI3Kδ inhibitor that was developed by Incyte Corporation as an antineoplastic and immunomodulatory agent, as claimed in their patent WO2014134426A1 [1]. The chemical structure is one of those claimed in patent WO2013033569A1, but it was not immediately clear which example it was from a mixture of diastereoisomers 345-348 (347 and 348 had the highest inhibitory potency vs. PI3Kδ and 347 was tested in vivo) [2]. The 2019 disclosure by Yue et al. confirmed the structure as patent example 346 [4]. Preclinical and phase 1/2 clinical evidence suggests that compared to first-generation PI3Kδ inhibitors, parsaclisib has reduced hepatotoxicity [3].
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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
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 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.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 107.95
Molecular weight 432.15
XLogP 2.88
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCOc1c(C2CNC(=O)C2)c(F)c(cc1[C@@H](n1nc(c2c1ncnc2N)C)C)Cl
Isomeric SMILES CCOc1c(C2CNC(=O)C2)c(F)c(cc1[C@@H](n1nc(c2c1ncnc2N)C)C)Cl
InChI InChI=1S/C20H22ClFN6O2/c1-4-30-18-12(6-13(21)17(22)16(18)11-5-14(29)24-7-11)10(3)28-20-15(9(2)27-28)19(23)25-8-26-20/h6,8,10-11H,4-5,7H2,1-3H3,(H,24,29)(H2,23,25,26)/t10-,11?/m0/s1
InChI Key ZQPDJCIXJHUERQ-VUWPPUDQSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
10589 parsaclisib
Synonyms Click here for help
compound 20 [PMID: 31749910] | IBI376 | INCB-050465
Database Links Click here for help
BindingDB Ligand 261326
CAS Registry No. 1426698-88-5 (source: WHO INN record)
GtoPdb PubChem SID 381118808
PubChem CID 89420683
Search Google for chemical match using the InChIKey ZQPDJCIXJHUERQ-VUWPPUDQSA-N
Search Google for chemicals with the same backbone ZQPDJCIXJHUERQ
Search PubMed clinical trials parsaclisib
Search PubMed titles parsaclisib
Search PubMed titles/abstracts parsaclisib
UniChem Compound Search for chemical match using the InChIKey ZQPDJCIXJHUERQ-VUWPPUDQSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZQPDJCIXJHUERQ-VUWPPUDQSA-N