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GSK2556286   Click here for help

GtoPdb Ligand ID: 13078

Synonyms: GSK286
Compound class: Synthetic organic
Comment: GSK2556286 is a substituted 4-aryloxypiperidine identified from a screen of compounds that inhibit intracellular growth of Mycobacterium tuberculosis in human macrophage-like differentiated monocytes (THP-1 cell line) [2]. It has a novel cholesterol-dependent mechanism of action, with recent studies establishing it as an agonist of mycobacterial Rv1625c, a membrane-bound adenylyl cyclase [1-2]. GSK2556286 is under clinical development as a potential treatment for tuberculosis (TB).

GSK2556286 is commercially available from our sponsors

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 6
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 70.67
Molecular weight 329.39
XLogP 1.06
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 CC1=CC=CC(=C1C)OC2CCN(CC2)CC3=CC(=O)NC(=O)N3
Isomeric SMILES CC1=C(C(=CC=C1)OC2CCN(CC2)CC3=CC(=O)NC(=O)N3)C
InChI InChI=1S/C18H23N3O3/c1-12-4-3-5-16(13(12)2)24-15-6-8-21(9-7-15)11-14-10-17(22)20-18(23)19-14/h3-5,10,15H,6-9,11H2,1-2H3,(H2,19,20,22,23)
InChI Key AZOFJHATIPDIER-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-[[4-(2,3-dimethylphenoxy)piperidin-1-yl]methyl]-1H-pyrimidine-2,4-dione
Synonyms Click here for help
GSK286
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo GSK2556286
Other databases
CAS Registry No. 1210456-20-4 (source: Scifinder)
ChEMBL Ligand CHEMBL4650308
GtoPdb PubChem SID 491299860
PubChem CID 45833762
Search Google for chemical match using the InChIKey AZOFJHATIPDIER-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AZOFJHATIPDIER
UniChem Compound Search for chemical match using the InChIKey AZOFJHATIPDIER-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AZOFJHATIPDIER-UHFFFAOYSA-N

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
GSK2556286 (links to external site)
Cat. No. HY-147017