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VPC171   Click here for help

GtoPdb Ligand ID: 8895

Compound class: Synthetic organic
Comment: VPC171 is a positive allosteric modulator (PAM) of the adenosine A1 receptor (A1R). It is compound 9a in Aurelio et al. (2009) [1]. PAMs of the A1R are being investigated as a novel treatment approach for neuropathic pain [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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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 1
Rotatable bonds 4
Topological polar surface area 71.33
Molecular weight 347.06
XLogP 5.32
No. Lipinski's rules broken 1

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 Nc1scc(c1C(=O)c1ccccc1)c1cccc(c1)C(F)(F)F
Isomeric SMILES Nc1scc(c1C(=O)c1ccccc1)c1cccc(c1)C(F)(F)F
InChI InChI=1S/C18H12F3NOS/c19-18(20,21)13-8-4-7-12(9-13)14-10-24-17(22)15(14)16(23)11-5-2-1-3-6-11/h1-10H,22H2
InChI Key HNHLVOBHWXLIGP-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. Aurelio L, Valant C, Flynn BL, Sexton PM, Christopoulos A, Scammells PJ. (2009)
Allosteric modulators of the adenosine A1 receptor: synthesis and pharmacological evaluation of 4-substituted 2-amino-3-benzoylthiophenes.
J Med Chem, 52 (14): 4543-7. [PMID:19514747]
2. Imlach WL, Bhola RF, May LT, Christopoulos A, Christie MJ. (2015)
A Positive Allosteric Modulator of the Adenosine A1 Receptor Selectively Inhibits Primary Afferent Synaptic Transmission in a Neuropathic Pain Model.
Mol Pharmacol, 88 (3): 460-8. [PMID:26104547]
3. Nguyen AT, Vecchio EA, Thomas T, Nguyen TD, Aurelio L, Scammells PJ, White PJ, Sexton PM, Gregory KJ, May LT et al.. (2016)
Role of the Second Extracellular Loop of the Adenosine A1 Receptor on Allosteric Modulator Binding, Signaling, and Cooperativity.
Mol Pharmacol, 90 (6): 715-725. [PMID:27683013]