VK2809   Click here for help

GtoPdb Ligand ID: 12768

Synonyms: compound 22c [PMID: 18975928] | MB-07811 | MB07811 | VK-2809
Compound class: Synthetic organic
Comment: VK2809 (MB07811) was a first-in-class, liver-targeting, thyroid hormone receptor-β agonist prodrug that was intended to lower serum cholesterol and triglycerides as a novel treament for primary hypercholesterolemia and non-alcoholic fatty liver disease [2-5].
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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

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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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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(C)C1=CC(=CC=C1O)CC2=C(C)C=C(C=C2C)OC[P@@]3(=O)OCC[C@@H](C4=CC=CC(=C4)Cl)O3
Isomeric SMILES CC(C)C1=C(O)C=CC(CC2=C(C)C=C(OC[P@@]3(=O)OCC[C@H](O3)C4=CC(Cl)=CC=C4)C=C2C)=C1
InChI InChI=1S/C28H32ClO5P/c1-18(2)25-14-21(8-9-27(25)30)15-26-19(3)12-24(13-20(26)4)32-17-35(31)33-11-10-28(34-35)22-6-5-7-23(29)16-22/h5-9,12-14,16,18,28,30H,10-11,15,17H2,1-4H3/t28-,35+/m0/s1
InChI Key LGGPZDRLTDGYSQ-JADSYQMUSA-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. Boyer SH, Jiang H, Jacintho JD, Reddy MV, Li H, Li W, Godwin JL, Schulz WG, Cable EE, Hou J et al.. (2008)
Synthesis and biological evaluation of a series of liver-selective phosphonic acid thyroid hormone receptor agonists and their prodrugs.
J Med Chem, 51 (22): 7075-93. [PMID:18975928]
2. Coppola M, Glinni D, Moreno M, Cioffi F, Silvestri E, Goglia F. (2014)
Thyroid hormone analogues and derivatives: Actions in fatty liver.
World J Hepatol, 6 (3): 114-29. [PMID:24672641]
3. Erion MD, Cable EE, Ito BR, Jiang H, Fujitaki JM, Finn PD, Zhang BH, Hou J, Boyer SH, van Poelje PD et al.. (2007)
Targeting thyroid hormone receptor-beta agonists to the liver reduces cholesterol and triglycerides and improves the therapeutic index.
Proc Natl Acad Sci U S A, 104 (39): 15490-5. [PMID:17878314]
4. Ito BR, Zhang BH, Cable EE, Song X, Fujitaki JM, MacKenna DA, Wilker CE, Chi B, van Poelje PD, Linemeyer DL et al.. (2009)
Thyroid hormone beta receptor activation has additive cholesterol lowering activity in combination with atorvastatin in rabbits, dogs and monkeys.
Br J Pharmacol, 156 (3): 454-65. [PMID:19183199]
5. Wirth EK, Puengel T, Spranger J, Tacke F. (2022)
Thyroid hormones as a disease modifier and therapeutic target in nonalcoholic steatohepatitis.
Expert Rev Endocrinol Metab, 17 (5): 425-434. [PMID:35957531]