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zinc pyrithione   Click here for help

GtoPdb Ligand ID: 2597

Approved drug
zinc pyrithione is an approved drug
Compound class: Synthetic organic
Comment: Pyrithione (PubChem CID 1570) is a zinc ionophore with broad-spectrum antibacterial activity against both against Gram-negative and Gram-positive bacteria and also antifungal activity [1]. We show the structure in complex with zinc which is the active ingredient found in medicated skin and hair care products.
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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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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 0
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 53.88
Molecular weight 317.71
XLogP 2.47
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 [S-]c1cccc[n+]1[O-].[S-]c1cccc[n+]1[O-].[Zn+2]
Isomeric SMILES [S-]c1cccc[n+]1[O-].[S-]c1cccc[n+]1[O-].[Zn+2]
InChI InChI=1S/2C5H5NOS.Zn/c2*7-6-4-2-1-3-5(6)8;/h2*1-4,8H;/q;;+2/p-2
InChI Key OTPSWLRZXRHDNX-UHFFFAOYSA-L

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. PANSY FE, STANDER H, KOERBER WL, DONOVICK R. (1953)
In vitro studies with 1-hydroxy-2(1H) pyridinethione.
Proc Soc Exp Biol Med, 82 (1): 122-4. [PMID:13037820]
2. Xiong Q, Sun H, Li M. (2007)
Zinc pyrithione-mediated activation of voltage-gated KCNQ potassium channels rescues epileptogenic mutants.
Nat Chem Biol, 3 (5): 287-96. [PMID:17435769]