roginolisib   Click here for help

GtoPdb Ligand ID: 12487

Synonyms: compound 1 [WO2022207646A1] | compound 339 [US9073940] [1] | IOA244 | MSC-2360844 | MSC2360844
Compound class: Synthetic organic
Comment: A name-to-structure disclosure was made in Spring 2023 [2], which confirmed our speculation that compound 1 that we had previously identified from WO2022207646A1 is iOnctura's semi-allosteric, PI3Kδ-selective inhibitor IOA-244 [3]; indeed the structure in WO2022207646 mapped to the synonym IOA-244 in PubChem CID 66580799, and the code is used in the patent (although it's not explicitly associated to compound 1). The same chemical structure was claimed in a 2015 Merck patent [1]. Publication of proposed INN list 129 (August 2023) confirmed our expectation that IOA-244 is "roginolisib".
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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 9
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 100.13
Molecular weight 526.58
XLogP -0.71
No. Lipinski's rules broken 1
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 C1=CC2=C(C(=C1)F)S(=O)(=O)CC3=C2N(C4=CC=C(C=C4)CN5CCOCC5)N=C3C(=O)N6CCOCC6
Isomeric SMILES FC1=CC=CC2=C1S(=O)(=O)CC3=C2N(N=C3C(=O)N4CCOCC4)C5=CC=C(CN6CCOCC6)C=C5
InChI InChI=1S/C26H27FN4O5S/c27-22-3-1-2-20-24-21(17-37(33,34)25(20)22)23(26(32)30-10-14-36-15-11-30)28-31(24)19-6-4-18(5-7-19)16-29-8-12-35-13-9-29/h1-7H,8-17H2
InChI Key NFHSJYKXENYICE-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[6-fluoro-1-[4-(morpholin-4-ylmethyl)phenyl]-5,5-dioxo-4H-thiochromeno[4,3-c]pyrazol-3-yl]-morpholin-4-ylmethanone
Synonyms Click here for help
compound 1 [WO2022207646A1] | compound 339 [US9073940] [1] | IOA244 | MSC-2360844 | MSC2360844
Database Links Click here for help
BindingDB Ligand 169989
ChEMBL Ligand CHEMBL3683575
GtoPdb PubChem SID 479821277
PubChem CID 66580799
Search Google for chemical match using the InChIKey NFHSJYKXENYICE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NFHSJYKXENYICE
UniChem Compound Search for chemical match using the InChIKey NFHSJYKXENYICE-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NFHSJYKXENYICE-UHFFFAOYSA-N