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AZ1   Click here for help

GtoPdb Ligand ID: 13348

PDB Ligand
Compound class: Synthetic organic
Comment: AZ1 is a sulfonyl piperazine compound with antibacterial activity, discovered using a high-throughput phenotypic screen [3]. It is a novel inhibitor of bacterial cell wall synthesis that acts by targeting UDP-2,3-diacylglucosamine hydrolase (LpxH), an enzyme in the lipopolysaccharide synthesis pathway [1]. LpxH is an essential enzyme, conserved in the majority of Gram-negative bacteria but absent in human, and an attractive target for antibacterial development.

AZ1 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 6
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 69.31
Molecular weight 453.48
XLogP 1.31
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 CC(=O)N1CCC2=CC(=CC=C21)S(=O)(=O)N3CCN(CC3)C4=CC(=CC=C4)C(F)(F)F
Isomeric SMILES CC(=O)N1CCC2=C1C=CC(=C2)S(=O)(=O)N3CCN(CC3)C4=CC=CC(=C4)C(F)(F)F
InChI InChI=1S/C21H22F3N3O3S/c1-15(28)27-8-7-16-13-19(5-6-20(16)27)31(29,30)26-11-9-25(10-12-26)18-4-2-3-17(14-18)21(22,23)24/h2-6,13-14H,7-12H2,1H3
InChI Key JRTCXCIMCOKGMN-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
1-[5-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]sulfonyl-2,3-dihydroindol-1-yl]ethanone
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo AZ1
Other databases
CAS Registry No. 901260-40-0 (source: Scifinder)
GtoPdb PubChem SID 496703318
PubChem CID 16002750
RCSB PDB Ligand OKV
Search Google for chemical match using the InChIKey JRTCXCIMCOKGMN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JRTCXCIMCOKGMN
UniChem Compound Search for chemical match using the InChIKey JRTCXCIMCOKGMN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JRTCXCIMCOKGMN-UHFFFAOYSA-N

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MedChemExpress
LpxH-IN-AZ1 (links to external site)
Cat. No. HY-130836