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dapansutrile   Click here for help

GtoPdb Ligand ID: 10056

Synonyms: OLT-1177 | OLT1177
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Dapansutrile (OLT1177) acts as a NLRP3 inflammasome inhibitor. It is a clinical candidate that is being developed by Olatec Therapeutics. Inhibition of the NLRP3 inflammasome reduces maturation of the pro-inflammatory, disease-associated cytokines IL-1β and IL-18 [3]. Immunoprecipitation and FRET analysis indicates that OLT1177 inhibits inflammasome oligomerization by blocking NLRP3-ASC, and NLRP3-caspase-1 interaction, but may also directly target NLRP3 (as assessed by inhibition of recombinant NLRP3 ATPase activity by dapansutrile) [3].

dapansutrile 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 0
Rotatable bonds 2
Topological polar surface area 66.31
Molecular weight 133.02
XLogP -0.32
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 N#CCCS(=O)(=O)C
Isomeric SMILES N#CCCS(=O)(=O)C
InChI InChI=1S/C4H7NO2S/c1-8(6,7)4-2-3-5/h2,4H2,1H3
InChI Key LQFRYKBDZNPJSW-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-methylsulfonylpropanenitrile
International Nonproprietary Names Click here for help
INN number INN
10228 dapansutrile
Synonyms Click here for help
OLT-1177 | OLT1177
Database Links Click here for help
CAS Registry No. 54863-37-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL3989943
GtoPdb PubChem SID 375973244
PubChem CID 12714644
Search Google for chemical match using the InChIKey LQFRYKBDZNPJSW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LQFRYKBDZNPJSW
Search PubMed clinical trials dapansutrile
Search PubMed titles dapansutrile
Search PubMed titles/abstracts dapansutrile
UniChem Compound Search for chemical match using the InChIKey LQFRYKBDZNPJSW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey LQFRYKBDZNPJSW-UHFFFAOYSA-N

Product suppliers

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Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Dapansutrile (links to external site)
Cat. No. HY-17629