GIV3727   Click here for help

GtoPdb Ligand ID: 9112

Compound class: Synthetic organic
Comment: GIV3727 is an orthosteric antagonist of the human bitterness receptor TAS2R31 [1]. It inhibits the receptor's activation by the commonly used artificial sweeteners, saccharin and acesulfame K. It also antagonises the highly similar TAS2R43 receptor. This is one of the compounds claimed in patent WO2008119196, covering the use of compounds to mask the off-notes that can be detected in consumables containing artificial sweeteners [2].
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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 4
Topological polar surface area 37.3
Molecular weight 198.16
XLogP 4.81
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 CC1CCC(C1(C)C)CCCC(=O)O
Isomeric SMILES CC1CCC(C1(C)C)CCCC(=O)O
InChI InChI=1S/C12H22O2/c1-9-7-8-10(12(9,2)3)5-4-6-11(13)14/h9-10H,4-8H2,1-3H3,(H,13,14)
InChI Key LYFXCRCUENNESS-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/)
References
1. Slack JP, Brockhoff A, Batram C, Menzel S, Sonnabend C, Born S, Galindo MM, Kohl S, Thalmann S, Ostopovici-Halip L et al.. (2010)
Modulation of bitter taste perception by a small molecule hTAS2R antagonist.
Curr Biol, 20 (12): 1104-9. [PMID:20537538]
2. Ungureanu IM, Brune NEI, Slack JP, Gray K, Simons CT, Evans PJE. (2008)
Off-note blocking sensory organic compounds.
Patent number: WO2008119196 A1. Assignee: Givaudan Sa. Priority date: 30/03/2007. Publication date: 09/10/2008.