ractopamine   Click here for help

GtoPdb Ligand ID: 10455

Synonyms: EL-737 | Optaflexx® | Paylean® | ractopamin | Tomax®
Compound class: Synthetic organic
Comment: Ractopamine exhibits agonist activity at the trace amine receptor 1 (TA1) [6] and β-adrenoceptors [2,5].

In some countries ractopamine is used as a feed additive in commercial livestock husbandry to increase lean meat mass. This use is banned in the EU and many other countries, but is permitted in countries including the US, Canada, Mexico, Japan and South Korea. Ractopamine's effect on human physiology has not been fully characterised, so the safety of consuming trace ractopamine in meat from treated animals remains controversial.

Commercially used ractopamine is administered as the hydrochloride salt and is a racemic mixture of all 4 possible stereoenantiomers. We show the structure without specified stereochemistry to represent the mixture.
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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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View interactive charts of activity data across species
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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Click here for structure editor
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 4
Rotatable bonds 7
Topological polar surface area 72.72
Molecular weight 301.17
XLogP 2.8
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(NCC(c1ccc(cc1)O)O)CCc1ccc(cc1)O
Isomeric SMILES CC(NCC(c1ccc(cc1)O)O)CCc1ccc(cc1)O
InChI InChI=1S/C18H23NO3/c1-13(2-3-14-4-8-16(20)9-5-14)19-12-18(22)15-6-10-17(21)11-7-15/h4-11,13,18-22H,2-3,12H2,1H3
InChI Key YJQZYXCXBBCEAQ-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/)
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
β2-adrenoceptor Hs Agonist Partial agonist 6.6 – 6.9 pKi - 1,3-4
⤷ pKi 6.6 – 6.9 [1,3-4]
Description: Inhibitory constant determined from a standard radioligand displacement assay using human β2-adrenoceptors expressed in Sf-9 cells and [3H]CGP1217 as tracer.
β2-adrenoceptor Hs Agonist Partial agonist 7.6 – 7.8 pEC50 - 1,3
⤷ pEC50 7.6 – 7.8 [1,3]
TA1 receptor Mm Agonist Agonist 4.8 pEC50 - 6
⤷ pEC50 4.8 (EC50 1.6x10-5 M) [6]
Description: Measuring chloride conductance in oocytes coexpressing hCFTR and mTAAR1, as a as a sensor for intracellular cAMP modulation.