SU-3327   Click here for help

GtoPdb Ligand ID: 10703

Synonyms: compound 9 [PMID: 19271755] | halicin | SU3327
Compound class: Synthetic organic
Comment: SU3327 was originally identified as an inhibitor of the serine/threonine c-Jun N-terminal kinases (JNKs) [2]. It is substrate competitive (inhibiting the protein-protein interaction between JNK and the substrate JIP-1), and selective for JNK vs. p38 MAPK and Akt. SU3327 was shown to restore insulin sensitivity in mouse models of diabetes.
In the search for new antibacterials, artificial intelligence algorithms were used to identify novel chemotypes that were likely to have novel mechanisms of antibacterial activity. SU3327 (re-named as halicin) was identified by this process and in vitro and in vivo follow-up showed that it potently killed a wide range of difficult to treat, antibacterial-resistant bacterial strains [3]. The compound appears to disrupt the ability of bacteria to maintain an electrochemical gradient across their cell membranes which blocks their production of ATP for energy.
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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

SU-3327 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 CDK toolkit. 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 1
Rotatable bonds 3
Topological polar surface area 189.61
Molecular weight 260.94
XLogP 0.78
No. Lipinski's rules broken 0
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.

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Canonical SMILES [O-][N+](=O)c1cnc(s1)Sc1nnc(s1)N
Isomeric SMILES [O-][N+](=O)c1cnc(s1)Sc1nnc(s1)N
InChI InChI=1S/C5H3N5O2S3/c6-3-8-9-5(14-3)15-4-7-1-2(13-4)10(11)12/h1H,(H2,6,8)
InChI Key NQQBNZBOOHHVQP-UHFFFAOYSA-N
Bioactivity Comments
SU-3327 demonstrates in vitro activity against both Gram-positive and Gram-negative bacteria. The MIC for antibacterial activity is 16 μg/ml for Staphylococcus aureus, 32 μg/ml for Escherichia coli, 128 μg/ml for Acinetobacter baumannii, and 256 μg/ml for multidrug-resistant (MDR) clinical isolates of Acinetobacter baumannii [1].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
mitogen-activated protein kinase 8 Hs Inhibitor Inhibition 6.2 pIC50 - 2
⤷ pIC50 6.2 (IC50 7x10-7 M) [2]
Description: Biochemical inhibition in a LanthaScreen kinase activity assay.