STING agonist 3   Click here for help

GtoPdb Ligand ID: 10128

Synonyms: compound 3 [PMID: 30405246] | diABZI | diABZI STING agonist-1
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: This compound is an optimised derivative of STING agonist 2 that has improved solubility and improved potency in primary cells [4]. Like agonist 2 it is one of the chemical structures claimed in GlaxoSmithKline's patent WO2017175147A1 [1]. it behaves as a cyclic dinucleotide mimic to activate the STING pathway.

SARS-CoV-2: Preclinical experimental evidence (in mice) suggests that this STING agonist may be effective in controlling infection by a range of SARS-CoV-2 variants, including B.1.351 (the beta variant [3]) [2]. The mechanistic hypothesis is that directly activating STING transiently stimulates interferon (IFN) signalling and circumvents the virus' ability to block IFN activation in infected respiratory epithelial cells, and re-establishes the innate immune response to infection.
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 14
Hydrogen bond donors 4
Rotatable bonds 20
Topological polar surface area 246.59
Molecular weight 849.4
XLogP 2.36
No. Lipinski's rules broken 2
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 COc1cc(cc2c1n(CC=CCn1c(NC(=O)c3cc(nn3CC)C)nc3c1c(OCCCN1CCOCC1)cc(c3)C(=O)N)c(n2)NC(=O)c1cc(nn1CC)C)C(=O)N
Isomeric SMILES COc1cc(cc2c1n(C/C=C/Cn1c(NC(=O)c3cc(nn3CC)C)nc3c1c(OCCCN1CCOCC1)cc(c3)C(=O)N)c(n2)NC(=O)c1cc(nn1CC)C)C(=O)N
InChI InChI=1S/C42H51N13O7/c1-6-54-31(19-25(3)49-54)39(58)47-41-45-29-21-27(37(43)56)23-33(60-5)35(29)52(41)12-8-9-13-53-36-30(46-42(53)48-40(59)32-20-26(4)50-55(32)7-2)22-28(38(44)57)24-34(36)62-16-10-11-51-14-17-61-18-15-51/h8-9,19-24H,6-7,10-18H2,1-5H3,(H2,43,56)(H2,44,57)(H,45,47,58)(H,46,48,59)/b9-8+
InChI Key JGLMVXWAHNTPRF-CMDGGOBGSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1-[(2E)-4-[5-carbamoyl-2-(1-ethyl-3-methyl-1H-pyrazole-5-amido)-7-[3-(morpholin-4-yl)propoxy]-1H-1,3-benzodiazol-1-yl]but-2-en-1-yl]-2-(1-ethyl-3-methyl-1H-pyrazole-5-amido)-7-methoxy-1H-1,3-benzodiazole-5-carboxamide
Synonyms Click here for help
compound 3 [PMID: 30405246] | diABZI | diABZI STING agonist-1
Database Links Click here for help
GtoPdb PubChem SID 381118838
PubChem CID 131986624
Search Google for chemical match using the InChIKey JGLMVXWAHNTPRF-CMDGGOBGSA-N
Search Google for chemicals with the same backbone JGLMVXWAHNTPRF
UniChem Compound Search for chemical match using the InChIKey JGLMVXWAHNTPRF-CMDGGOBGSA-N
UniChem Connectivity Search for chemical match using the InChIKey JGLMVXWAHNTPRF-CMDGGOBGSA-N