mavorixafor   Click here for help

GtoPdb Ligand ID: 8580

Synonyms: AMD 070 | AMD-070 | AMD-11070 | AMD11070 | compound 2 [PMID: 20297846] | X4P-001 | X4P-001-IO | X4P-001-LD
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Mavorixafor (AMD070) is a potent, selective and bioavailable CXCR4 chemokine receptor allosteric antagonist [1]. Originally developed for HIV treatment, it is now being repurposed by X4 Pharmaceuticals as X4P-001 for the treatment of WHIM syndrome, a sub-type of a primary immunodeficiency disease caused by CXCR4 mutations. The compound is exemplified in a process patent US7332605 and as compound 89 from a series of 169 analogues in WO2003055876 but neither filing includes activity data.
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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 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 70.83
Molecular weight 349.23
XLogP 2.23
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 NCCCCN(C1CCCc2c1nccc2)Cc1nc2c([nH]1)cccc2
Isomeric SMILES NCCCCN([C@H]1CCCc2c1nccc2)Cc1nc2c([nH]1)cccc2
InChI InChI=1S/C21H27N5/c22-12-3-4-14-26(15-20-24-17-9-1-2-10-18(17)25-20)19-11-5-7-16-8-6-13-23-21(16)19/h1-2,6,8-10,13,19H,3-5,7,11-12,14-15,22H2,(H,24,25)/t19-/m0/s1
InChI Key WVLHHLRVNDMIAR-IBGZPJMESA-N
References
1. Skerlj RT, Bridger GJ, Kaller A, McEachern EJ, Crawford JB, Zhou Y, Atsma B, Langille J, Nan S, Veale D et al.. (2010)
Discovery of novel small molecule orally bioavailable C-X-C chemokine receptor 4 antagonists that are potent inhibitors of T-tropic (X4) HIV-1 replication.
J Med Chem, 53 (8): 3376-88. [PMID:20297846]
2. Wong RS, Bodart V, Metz M, Labrecque J, Bridger G, Fricker SP. (2008)
Comparison of the potential multiple binding modes of bicyclam, monocylam, and noncyclam small-molecule CXC chemokine receptor 4 inhibitors.
Mol Pharmacol, 74 (6): 1485-95. [PMID:18768385]