compound 46c [PMID: 29350534]   Click here for help

GtoPdb Ligand ID: 9883

Compound class: Synthetic organic
Comment: Compound 46c is a CXCR4 antagonist. It is a structural analogue of TIQ-15 [1]. CXCR4 antagonists are being developed for potential clinical utility as anti-cancer agents. Compared to TIQ-15, 46c has improved predicted intestinal permeability and reduced inhibition of CYP450 2D6, which is one of the most important hepatic drug-metabolising enzymes, and inhibition of which can cause adverse drug-drug interactions. These enhanced drug-like features make 46c a more suitable clinical lead than TIQ-15.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 49.42
Molecular weight 446.3
XLogP 3.05
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 O1CCC(CC1)NCC=CCN(C1CCCc2c1nccc2)CC1NCc2c(C1)cccc2
Isomeric SMILES O1CCC(CC1)NC/C=C/CN([C@H]1CCCc2c1nccc2)C[C@@H]1NCc2c(C1)cccc2
InChI InChI=1S/C28H38N4O/c1-2-8-24-20-31-26(19-23(24)7-1)21-32(16-4-3-14-29-25-12-17-33-18-13-25)27-11-5-9-22-10-6-15-30-28(22)27/h1-4,6-8,10,15,25-27,29,31H,5,9,11-14,16-21H2/b4-3+/t26-,27+/m1/s1
InChI Key QPAGOTNPJABYCP-FITNPZAZSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CXCR4 Mm Antagonist Antagonist 8.0 pIC50 - 1
⤷ pIC50 8.0 (IC50 9.24x10-9 M) [1]
CXCR4 Hs Antagonist Antagonist 7.8 pIC50 - 1
⤷ pIC50 7.8 (IC50 1.55x10-8 M) [1]
Description: Measuring antagonist-mediated inhibition of CXCL12-induced calcium flux in human T lymphoblast CCRF-CEM cells.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CYP2D6 Hs Inhibitor Inhibition 5.6 pIC50 - 1
⤷ pIC50 5.6 (IC50 2.61x10-6 M) [1]