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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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.

✖
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
Selectivity at ligand targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CXCL12α Primary target of this compound Hs Inhibitor Binding 6.6 pIC50 - 1
⤷ pIC50 6.6 (IC50 2.67x10-7 M) [1]
Description: Measuring competitive inhibition of CXCL12α binding to CXCR4 by test ligand, using FRET detection.