HSGN-218   Click here for help

GtoPdb Ligand ID: 13054

Compound class: Synthetic organic
Comment: HSGN-218 is the lead compound from a series of halogenated N-(1,3,4-oxadiazol-2-yl)benzamides with potent antibacterial activity against Gram-positive bacteria, including Clostridioides difficile [1].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 88.35
Molecular weight 434.22
XLogP 4.63
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES C1=C(C=CC(=C1)SC(F)(F)F)C(=O)NC2=NN=C(C3=CC(=CC(=C3)Cl)Cl)O2
Isomeric SMILES C1=CC(=CC=C1C(=O)NC2=NN=C(O2)C3=CC(=CC(=C3)Cl)Cl)SC(F)(F)F
InChI InChI=1S/C16H8Cl2F3N3O2S/c17-10-5-9(6-11(18)7-10)14-23-24-15(26-14)22-13(25)8-1-3-12(4-2-8)27-16(19,20)21/h1-7H,(H,22,24,25)
InChI Key YNSLXRYEPGHGRY-UHFFFAOYSA-N
No information available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mechanism by which HSGN-218 inhibits bacterial growth has been studied and appears to involve multiple bacterial pathways [2]. This study revealed that HSGN-218 downregulates a number of essential proteins, including Pol IIIC that is necessary for DNA replication and is a novel and specific drug target for Gram-positive pathogens. In addition, the compound is involved in heme regulation, menaquinone biosynthesis, siderophore biosynthesis and is able to depolarize bacterial membranes.