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RIPK1 inhibitor 22b   Click here for help

GtoPdb Ligand ID: 10155

Synonyms: compound 22b [PMID: 30480444]
Compound class: Synthetic organic
Comment: Compound 22b represents a novel chemical scaffold class for receptor-interacting protein kinase 1 (RIPK1) inhibitors [1]. It has shown anti-metastasis activity in the experimental B16 melanoma lung metastasis model. The molecular mechanism underlying this effect is identified as inhibition of tumour-dependent RIPK1-induced programmed necrosis (necroptosis) of vascular endothelial cells, which facilitates tumour cell extravasation and metastasis. Compound 22b is a type II kinase inhibitor that interacts with the inactive conformation (DFG-out) of the RIPK1 kinase domain.
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Ligand Activity Visualisation Charts

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View interactive charts of activity data across species

RIPK1 inhibitor 22b is commercially available from our sponsors

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 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 86.27
Molecular weight 481.17
XLogP 5.04
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 CCn1cc(c2c1ncnc2N)c1ccc2c(c1)CCN2C(=O)Cc1cccc(c1)OC(F)(F)F
Isomeric SMILES CCn1cc(c2c1ncnc2N)c1ccc2c(c1)CCN2C(=O)Cc1cccc(c1)OC(F)(F)F
InChI InChI=1S/C25H22F3N5O2/c1-2-32-13-19(22-23(29)30-14-31-24(22)32)16-6-7-20-17(12-16)8-9-33(20)21(34)11-15-4-3-5-18(10-15)35-25(26,27)28/h3-7,10,12-14H,2,8-9,11H2,1H3,(H2,29,30,31)
InChI Key APPXQUDJLJXULP-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1-(5-{4-Amino-7-ethyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2,3-dihydro-1H-indol-1-yl)-2-[3-(trifluoromethoxy)phenyl]ethan-1-one
Synonyms Click here for help
compound 22b [PMID: 30480444]
Database Links Click here for help
GtoPdb PubChem SID 381118865
PubChem CID 137321158
Search Google for chemical match using the InChIKey APPXQUDJLJXULP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone APPXQUDJLJXULP
UniChem Compound Search for chemical match using the InChIKey APPXQUDJLJXULP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey APPXQUDJLJXULP-UHFFFAOYSA-N

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MedChemExpress
RIPK1-IN-7 (links to external site)
Cat. No. HY-119933