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lolamicin   Click here for help

GtoPdb Ligand ID: 13410

Compound class: Synthetic organic
Comment: Lolamicin is an antibacterial with potential to avoid disruption of the gut microbiota. It has specific activity against Gram-negative pathogenic bacteria, while selectively sparing Gram-negative and Gram-positive commensal strains [2]. Lolamicin is an inhibitor of lipoprotein CDE (LolCDE) [2], a complex found in the membrane of Gram-negative bacteria. It is one of the chemical structures claimed in patent WO2023091873A1 from the University of Illinois [1].

lolamicin 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 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 69.77
Molecular weight 380.44
XLogP 2.45
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=NC(=CC(=C1)C2=C(C3=CC(=CC=C3)OCC4=CC(=CC=C4)C#N)NN=C2)C
Isomeric SMILES CC1=CC(=CC(=N1)C)C2=C(NN=C2)C3=CC(=CC=C3)OCC4=CC(=CC=C4)C#N
InChI InChI=1S/C24H20N4O/c1-16-9-21(10-17(2)27-16)23-14-26-28-24(23)20-7-4-8-22(12-20)29-15-19-6-3-5-18(11-19)13-25/h3-12,14H,15H2,1-2H3,(H,26,28)
InChI Key CIXIQLLJOWEAKU-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-[4-(2,6-dimethylpyridin-4-yl)-1H-pyrazol-5-yl]phenoxy]methyl]benzonitrile
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Lolamicin
Other databases
GtoPdb PubChem SID 496703380
PubChem CID 168894634
Search Google for chemical match using the InChIKey CIXIQLLJOWEAKU-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CIXIQLLJOWEAKU
UniChem Compound Search for chemical match using the InChIKey CIXIQLLJOWEAKU-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CIXIQLLJOWEAKU-UHFFFAOYSA-N

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MedChemExpress
Lolamicin (links to external site)
Cat. No. HY-164036