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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
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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 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
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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 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/)
References
1. Opperman TJ, Kwasny SM, Kim HS, Nguyen ST, Houseweart C, D'Souza S, Walker GC, Peet NP, Nikaido H, Bowlin TL. (2014)
Characterization of a novel pyranopyridine inhibitor of the AcrAB efflux pump of Escherichia coli.
Antimicrob Agents Chemother, 58 (2): 722-33. [PMID:24247144]
2. Sjuts H, Vargiu AV, Kwasny SM, Nguyen ST, Kim HS, Ding X, Ornik AR, Ruggerone P, Bowlin TL, Nikaido H et al.. (2016)
Molecular basis for inhibition of AcrB multidrug efflux pump by novel and powerful pyranopyridine derivatives.
Proc Natl Acad Sci U S A, 113 (13): 3509-14. [PMID:26976576]
3. Vargiu AV, Ruggerone P, Opperman TJ, Nguyen ST, Nikaido H. (2014)
Molecular mechanism of MBX2319 inhibition of Escherichia coli AcrB multidrug efflux pump and comparison with other inhibitors.
Antimicrob Agents Chemother, 58 (10): 6224-34. [PMID:25114133]