LIT-927   Click here for help

GtoPdb Ligand ID: 10075

Synonyms: compound 57 [PMID: 30106292]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: LIT-927 is a small molecule that binds to and neutralises the chemokine CXCL12 [1]. It has been termed a 'neutraligand'. LIT-927 was developed as an alternative strategy to inhibitors for CXCL12's cognate receptors CXCR4 or CXCR7, as a potential anti-inflammatory agent.
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 CDK toolkit. 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 2
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 75.21
Molecular weight 328.06
XLogP 4.27
No. Lipinski's rules broken 0
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.

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Canonical SMILES COc1cc(ccc1O)c1[nH]c(=O)nc(c1)c1ccc(cc1)Cl
Isomeric SMILES COc1cc(ccc1O)c1[nH]c(=O)nc(c1)c1ccc(cc1)Cl
InChI InChI=1S/C17H13ClN2O3/c1-23-16-8-11(4-7-15(16)21)14-9-13(19-17(22)20-14)10-2-5-12(18)6-3-10/h2-9,21H,1H3,(H,19,20,22)
InChI Key BYYRNPIGDRRGLJ-UHFFFAOYSA-N
Immunopharmacology Comments
LIT-927 exhibits high binding selectivity for CXCL12 over other chemokines. Orally delivered LIT-927 reduces eosinophil recruitment in a murine model of allergic airway hypereosinophilia, indicating potential efficacy as an anti-asthmatic agent [1]. It offers a pharmacological tool that is suitable for the investigation of CXCL12 physiology in vivo and for further exploration of the utility/efficacy of chemokine neutralisation as a pharmacological strategy in inflammatory and related diseases.