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diacylglycerol kinase inhibitor II   Click here for help

GtoPdb Ligand ID: 5957

Synonyms: R 59 949 | R59949
Compound class: Synthetic organic
Comment: This compound inhibits diacylglycerol kinase activity [2].

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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 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 73.12
Molecular weight 489.17
XLogP 6.89
No. Lipinski's rules broken 1

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 Fc1ccc(cc1)C(=C1CCN(CC1)CCn1c(=S)[nH]c2c(c1=O)cccc2)c1ccc(cc1)F
Isomeric SMILES Fc1ccc(cc1)C(=C1CCN(CC1)CCn1c(=S)[nH]c2c(c1=O)cccc2)c1ccc(cc1)F
InChI InChI=1S/C28H25F2N3OS/c29-22-9-5-19(6-10-22)26(20-7-11-23(30)12-8-20)21-13-15-32(16-14-21)17-18-33-27(34)24-3-1-2-4-25(24)31-28(33)35/h1-12H,13-18H2,(H,31,35)
InChI Key ZCNBZFRECRPCKU-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/)
Bioactivity Comments
R59949 selectively inhibits Ca2+-activated diacylglycerol kinases, whilst the Ca2+-independent DGKs are almost totally insensitive to this compound [4]. In in vitro assays using various purified DGK preparations, R59949 inhibits enzyme activity by between 70-95% for the Ca2+-activated DGKs, but by only 18-22% for the Ca2+-independent DGKs [4]. R59949 inhibits DGK in isolated platelet membranes and in intact platelets with IC50 values of 300 and 120 nM respectively [2].