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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].

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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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Click here for structure editor
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/)
References
1. Hergenrother PJ, Muñoz KA. (2023)
Gram-negative specific antibiotics sparing effect on gut microbiome.
Patent number: WO2023091873A1. Assignee: The University Of Illinois. Priority date: 19/11/2021. Publication date: 25/05/2023.
2. Muñoz KA, Ulrich RJ, Vasan AK, Sinclair M, Wen PC, Holmes JR, Lee HY, Hung CC, Fields CJ, Tajkhorshid E et al.. (2024)
A Gram-negative-selective antibiotic that spares the gut microbiome.
Nature, 630 (8016): 429-436. [PMID:38811738]