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MAC13243   Click here for help

GtoPdb Ligand ID: 14301

Compound class: Synthetic organic
Comment: MAC13243 is the lead from a novel class of antibacterial compounds that target bacterial outer-membrane lipoprotein carrier protein (LolA) [2]. It has selective activity against Gram-negative bacteria [2]. Note that we show the structure for the free base form of the compound, but strictly MAC13243 is the hydrochloride salt formulation (PubChem CID 2806781; CAS number 1071638-38-4).
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 1
Rotatable bonds 8
Topological polar surface area 71.39
Molecular weight 405.94
XLogP 2.21
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 COC1=CC=C(CCN2CNC(=NC2)SCC3=CC=C(C=C3)Cl)C=C1OC
Isomeric SMILES COC1=C(C=C(C=C1)CCN2CNC(=NC2)SCC3=CC=C(C=C3)Cl)OC
InChI InChI=1S/C20H24ClN3O2S/c1-25-18-8-5-15(11-19(18)26-2)9-10-24-13-22-20(23-14-24)27-12-16-3-6-17(21)7-4-16/h3-8,11H,9-10,12-14H2,1-2H3,(H,22,23)
InChI Key JRZNGLZDQHVIOO-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/)
Bioactivity Comments
MAC13243 demonstrates specific Gram-negative activity, with an MIC of 16 μg/ml against Escherichia coli and 4 μg/ml against Pseudomonas aeruginosa [2]. It shows no cytotoxicity towards HeLa cells (≥16-64x MIC) [2].
The dissociation constant (Kd) for the MAC13243-LolA complex is 7.5 ± 3 μM [2].