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denatonium   Click here for help

GtoPdb Ligand ID: 12433

PDB Ligand
Compound class: Synthetic organic
Comment: Denatonium (benzoate) is the bitter-testing compound that is contained in Bitrex® (a product that is added to many household products, as a safety measure, to make them unpleasant to consume/drink).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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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 1
Rotatable bonds 8
Topological polar surface area 29.1
Molecular weight 325.47
XLogP 2.24
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 CC[N+](CC)(CC1=CC=CC=C1)CC(=O)NC2=C(C)C=CC=C2C
Isomeric SMILES CC[N+](CC)(CC1=CC=CC=C1)CC(=O)NC2=C(C=CC=C2C)C
InChI InChI=1S/C21H28N2O/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4/h7-14H,5-6,15-16H2,1-4H3/p+1
InChI Key ZFQMTVNLDNXRNQ-UHFFFAOYSA-O

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/)
No information available.
Summary of Clinical Use Click here for help
Denatonium acetate (ARD-101) was progressed as a clinical candidate, proposed to reduce food-intake (by promoting satiety) in people with the rare genetic condition Prader-Willi syndrome (a major manifestation of which is hyperphagia leading to obesity). The HERO phase 3 trial was paused as a precautionary measure in early 2026 due to concerns of 'reversible cardiac observations' in healthy trial participants who had received above target therapeutic doses of ARD-101. Given that TAS2Rs are expressed in cardiac tissue [1-2,5], this could potentially reflect an on-target/mechanism-based outcome.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
TAS2Rs are expressed on enteroendocrine cells of the digestive tract. Agonist-mediated activation of signalling through these receptors stimulates release of gut-peptide hormones such as GLP-1 (glucagon-like peptide 1; mimicked by weight loss drugs such as semaglutide) and cholecystokinins (satiety hormones). The effects of the released hormones is proposed to stimulate gut-brain neurologic signalling and reduce feelings of hunger.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT07197034 The Hunger Elimination or Reduction Objective (HERO ) Open -Label Extension (OLE) Trial Phase 3 Interventional Aardvark Therapeutics, Inc.
NCT06828861 ARD-101 for Treatment of PWS: The Hunger Elimination or Reduction Objective Trial Phase 3 Interventional Aardvark Therapeutics, Inc.
NCT05153434 A Study of Oral ARD-101 in Patients With Prader-Willi Syndrome Phase 2 Interventional Aardvark Therapeutics, Inc.
NCT05121441 Study to Evaluate ARD-101 in Adults With Obesity Phase 2 Interventional Aardvark Therapeutics, Inc.