SB269652   Click here for help

GtoPdb Ligand ID: 7694

Synonyms: SB-269,652 | SB-269652
Compound class: Synthetic organic
Comment: SB269652 was originally described as an allosteric antagonist at dopamine D3 and D2 receptors [4]. Further analysis has revealed a novel mechanism of allostery, which relies on the presence of receptor dimers [2]. SB269652 acts as a bitopic ligand [3], with one pharmacophore binding to one receptor protomer and the other pharmacophore allosterically modulating the binding of a ligand on the second partner in the dimer, in this instance rendering the compound a negative allosteric regulator of dopamine binding to the D2 receptor [2].
PubChem CID 9910352 represents the compound structure without specified stereochemistry.
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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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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 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 71.92
Molecular weight 426.24
XLogP 4.57
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 N#Cc1ccc2c(c1)CN(CC2)CCC1CCC(CC1)NC(=O)c1cc2c([nH]1)cccc2
Isomeric SMILES N#Cc1ccc2c(c1)CN(CC2)CC[C@@H]1CC[C@H](CC1)NC(=O)c1cc2c([nH]1)cccc2
InChI InChI=1S/C27H30N4O/c28-17-20-5-8-21-12-14-31(18-23(21)15-20)13-11-19-6-9-24(10-7-19)29-27(32)26-16-22-3-1-2-4-25(22)30-26/h1-5,8,15-16,19,24,30H,6-7,9-14,18H2,(H,29,32)/t19-,24-
InChI Key JGLGOAQPUQITLD-OGAOHHHESA-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/)
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel