ETX0462   Click here for help

GtoPdb Ligand ID: 11753

Synonyms: ETX-0462 | VMM
PDB Ligand
Compound class: Synthetic organic
Comment: ETX0462 is a diazabicyclooctane molecule that represents a new class of antibacterial. It is a β-lactamase inhibitor that also acts as a single agent antibacterial through its capacity to inhibit penicillin-binding proteins [1]. It has a broad-spectrum of activity (in vitro and in vivo) against Gram-negative bacteria including virulent and antibacterial resistant ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species), Stenotrophomonas maltophilia and bacterial agents that might be used as biological weapons. Further optimisation of ETX0462 is required to improve its permeability across bacterial outer membranes and increase its biochemical potency.
The crystal structure of ETX0462 bound to P. aeruginosa penicillin binding protein 3 (PBP3) has been resolved at a resolution of 2.2 Å (PDB ID: 7JWL) [1].
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 8
Hydrogen bond donors 5
Rotatable bonds 6
Topological polar surface area 186.99
Molecular weight 364.08
XLogP -2.32
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 CN=C([C@H]1N(C[C@@H](c2c1n(C)nc2)NOS(=O)(=O)O)C(=O)O)NO
Isomeric SMILES CN=C([C@@H]1c2c(cnn2C)[C@H](CN1C(=O)O)NOS(=O)(=O)O)NO
InChI InChI=1S/C10H16N6O7S/c1-11-9(13-19)8-7-5(3-12-15(7)2)6(4-16(8)10(17)18)14-23-24(20,21)22/h3,6,8,14,19H,4H2,1-2H3,(H,11,13)(H,17,18)(H,20,21,22)/t6-,8-/m0/s1
InChI Key TVYRNFNEBLNAMJ-XPUUQOCRSA-N
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel