pasodacigib   Click here for help

GtoPdb Ligand ID: 13751

Synonyms: Example 298 [US11998539B2]
Compound class: Synthetic organic
Comment: Pasodacigib is the INN for a diacylglycerol kinase (DGK) inhibitor. A structural match via PubChem reveals that it is one of the claims in Bayer patent US11998539B2. There are two diacylglycerol kinase inhibitors (one each for DGKα and DGKζ) listed in the oncology section of Bayer's development pipeline page [1], but no internal code numbers have been ascribed to these. However patent US11998539B2 claims DGKα inhibitors, so it would be reasonable to assume pasodacigib to be a DGKα inhibitor. Further, the record for Bayer-led clinical trial (NCT05858164) lists the drug intervention as BAY2862789, which is recorded by the US National Cancer Institute's drug definition service as a DGKα inhibitor [2]. We must wait for formal disclosure of BAY2862789's structure before equating the INN to BAY2862789.

DGK inhibition mediates T cell activation, and this mechanism is being leveraged to promote a clinically beneficial anti-tumour immune response.
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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 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.

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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 88.23
Molecular weight 434.46
XLogP 1.7
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
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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.

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/)

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Canonical SMILES CC1=CC2=C(C=C1)OC(=N2)C3CCN(CC3)C4=C(C(=O)N)C(=O)N(C)C5=C4C=C(C=C5)F
Isomeric SMILES CC1=CC2=C(C=C1)OC(=N2)C3CCN(CC3)C4=C(C(=O)N(C5=C4C=C(C=C5)F)C)C(=O)N
InChI InChI=1S/C24H23FN4O3/c1-13-3-6-19-17(11-13)27-23(32-19)14-7-9-29(10-8-14)21-16-12-15(25)4-5-18(16)28(2)24(31)20(21)22(26)30/h3-6,11-12,14H,7-10H2,1-2H3,(H2,26,30)
InChI Key MOHUWNQEDDJZJK-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/)
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
diacylglycerol kinase alpha Hs Inhibitor Inhibition 9.3 pIC50 - 3
⤷ pIC50 9.3 (IC50 5x10-10 M) [3]