nibrozetone   Click here for help

GtoPdb Ligand ID: 13184

Synonyms: ABDNAZ [2] | RRx-001 | RRx001
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: RRx-001 (EpicentRx) was originally developed as an anti-tumour agent [3]; it promotes apoptosis, and has radio- , chemo- and immuno-sensitising actions in cancer models. It also provides cytoprotective effects in normal tissues, which has led to the proposal of RRx-001 as a supportive care drug in patients undergoing cytotoxic cancer therapy. RRx-001 was identified using phenotypic screening, so its molecular mechanism of action was initially unclear. Several mechanisms have subsequently been identified, including NLRP3 inflammasome inhibition [1,4] and CD47/SIRP-α immune checkpoint inhibition. RRx-001 covalently targets the cysteine 409 residue in NLRP3's NACHT domain and blocks NLRP3/NEK7 interaction and assembly of the inflammasome complex. This ultimately inhibits release of active pro-inflammatory cytokines (IL-1β and IL-18).
RRx-001's chemical structure is a match for the INN nibrozetone (proposed INN list 130 of Feb. 2024).

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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 0
Rotatable bonds 4
Topological polar surface area 106.59
Molecular weight 268.02
XLogP 0.25
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 C(C(=O)N1CC(C1)([N+](=O)[O-])[N+](=O)[O-])Br
Isomeric SMILES BrCC(N1CC([N+]([O-])=O)([N+]([O-])=O)C1)=O
InChI InChI=1S/C5H6BrN3O5/c6-1-4(10)7-2-5(3-7,8(11)12)9(13)14/h1-3H2
InChI Key JODKFOVZURLVTG-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/)
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel