PBT2   Click here for help

GtoPdb Ligand ID: 11108

Synonyms: PBT-1033 | PBT-2 | PBT1033
Compound class: Synthetic organic
Comment: PBT2 is an orally administered, safe-in-humans zinc ionophore. Chemically it is an 8-hydroxyquinoline analogue. PBT2 has been classified as a metal-protein attenuating compound (MPAC), and is designed to interfere with zinc ion interactions with proteins.
Antibacterial activity: Whilst not active alone, PBT2 + zinc + antibacterial 'X' acts synergistically to overcome acquired bacterial-resistance to antibacterial 'X' (which can include clinically used antibacterials). This strategy produces activity against antibacterial-resistant Gram-positive pathogens [1].
SARS-CoV-2: Based on evidence from previous studies in MERS-CoV and SARS-CoV-1, zinc modulation (e.g. by PBT2 or disulfiram [4]) has been proposed as a potential mechanism for the prophylaxis/treatment of COVID-19. Altering zinc ion levels is predicted to affect activity of host and/or viral zinc-containing metalloenzymes.

PBT2 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 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 36.36
Molecular weight 270.03
XLogP 2.8
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 CN(Cc1ccc2c(n1)c(O)c(cc2Cl)Cl)C
Isomeric SMILES CN(Cc1ccc2c(n1)c(O)c(cc2Cl)Cl)C
InChI InChI=1S/C12H12Cl2N2O/c1-16(2)6-7-3-4-8-9(13)5-10(14)12(17)11(8)15-7/h3-5,17H,6H2,1-2H3
InChI Key YZPOQCQXOSEMAZ-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
5,7-dichloro-2-[(dimethylamino)methyl]quinolin-8-ol
Synonyms Click here for help
PBT-1033 | PBT-2 | PBT1033
Database Links Click here for help
CAS Registry No. 1123760-88-2 (source: ChemIDplus)
ChEMBL Ligand CHEMBL3634131
DrugBank Ligand DB05565
GtoPdb PubChem SID 434122168
PubChem CID 10016012
Search Google for chemical match using the InChIKey YZPOQCQXOSEMAZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YZPOQCQXOSEMAZ
UniChem Compound Search for chemical match using the InChIKey YZPOQCQXOSEMAZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YZPOQCQXOSEMAZ-UHFFFAOYSA-N

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MedChemExpress
PBT 1033 (links to external site)
Cat. No. HY-105321