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) [1]. 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 antibiotics, 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 diffucult to treat, antibiotic-resistant bacterial strains [2]. Halicin 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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2D Structure
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Physico-chemical Properties
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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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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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[(5-nitro-1,3-thiazol-2-yl)sulfanyl]-1,3,4-thiadiazol-2-amine
Synonyms Click here for help
compound 9 [PMID: 19271755] | halicin | SU3327
Database Links Click here for help
BindingDB Ligand 29315
CAS Registry No. 40045-50-9 (source: PubChem)
ChEMBL Ligand CHEMBL510038
GtoPdb PubChem SID 404859150
PubChem CID 11837140
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Tocris
SU 3327
Cat. No. 3607