GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

MBX2319   Click here for help

GtoPdb Ligand ID: 14411

PDB Ligand
Compound class: Synthetic organic
Comment: MBX2319 is a novel pyranopyridine compound that acts as a bacterial efflux pump inhibitor (EPI). It has potent activity against the resistance-nodulation-division (RND) family of efflux pumps of Enterobacteriaceae [1], binding to AcrB, a component of the AcrAB-TolC efflux pump [2-3]. EPIs have potential clinical utility as adjunctive therapeutic agents for the treatment of infections caused by Gram-negative pathogens.
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 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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 83.15
Molecular weight 409.55
XLogP 2.87
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
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.

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/)

✖
Canonical SMILES CC1(C)CC2=C(CO1)C(=NC(=C2C#N)SCCC3=CC=CC=C3)N4CCOCC4
Isomeric SMILES CC1(CC2=C(CO1)C(=NC(=C2C#N)SCCC3=CC=CC=C3)N4CCOCC4)C
InChI InChI=1S/C23H27N3O2S/c1-23(2)14-18-19(15-24)22(29-13-8-17-6-4-3-5-7-17)25-21(20(18)16-28-23)26-9-11-27-12-10-26/h3-7H,8-14,16H2,1-2H3
InChI Key CITLGGQQUFMBKB-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
3,3-dimethyl-8-morpholin-4-yl-6-(2-phenylethylsulfanyl)-1,4-dihydropyrano[4,5-d]pyridine-5-carbonitrile
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo MBX 2319
Other databases
CAS Registry No. 375836-83-2 (source: Scifinder)
ChEMBL Ligand CHEMBL3401827
GtoPdb PubChem SID 523352203
PubChem CID 1289417
RCSB PDB Ligand 5QG
Search Google for chemical match using the InChIKey CITLGGQQUFMBKB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CITLGGQQUFMBKB
UniChem Compound Search for chemical match using the InChIKey CITLGGQQUFMBKB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CITLGGQQUFMBKB-UHFFFAOYSA-N