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H-151   Click here for help

GtoPdb Ligand ID: 10122

Synonyms: H 151 | H151
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: H-151 is a small molecule covalent STING antagonist [2]. Mechanistically it binds to Cys91 of the protein and prevents its palmitoylation. The non-modified STING protein is then unable to assemble the STING complexes that are essential to activate downstream processes (e.g. Type I interferon response). H-151 has been reported to reduce SARS-CoV-2-induced lung inflammation and to improve disease outcome in ACE2-humanised mice [1].

H-151 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 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 56.92
Molecular weight 279.14
XLogP 3.86
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 CCc1ccc(cc1)NC(=O)Nc1c[nH]c2c1cccc2
Isomeric SMILES CCc1ccc(cc1)NC(=O)Nc1c[nH]c2c1cccc2
InChI InChI=1S/C17H17N3O/c1-2-12-7-9-13(10-8-12)19-17(21)20-16-11-18-15-6-4-3-5-14(15)16/h3-11,18H,2H2,1H3,(H2,19,20,21)
InChI Key UJZDIKVQFMCLBE-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
3-(4-ethylphenyl)-1-(1H-indol-3-yl)urea
Synonyms Click here for help
H 151 | H151
Database Links Click here for help
CAS Registry No. 941987-60-6 (source: PubChem)
GtoPdb PubChem SID 381118832
PubChem CID 7616033
Search Google for chemical match using the InChIKey UJZDIKVQFMCLBE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UJZDIKVQFMCLBE
UniChem Compound Search for chemical match using the InChIKey UJZDIKVQFMCLBE-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UJZDIKVQFMCLBE-UHFFFAOYSA-N

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MedChemExpress
H-151 (links to external site)
Cat. No. HY-112693