plerixafor   Click here for help

GtoPdb Ligand ID: 844

Synonyms: AMD 3100 | AMD3100 | bicyclam JM-2987 | JM 3100 | Mozobil®
Approved drug PDB Ligand Immunopharmacology Ligand
plerixafor is an approved drug (FDA (2008), EMA (2009))
Compound class: Synthetic organic
Comment: Plerixafor (AMD3100) is an antagonist of the chemokine (C-X-C motif) receptor 4 (CXCR4) [6]. It acts as a stem cell mobiliser.
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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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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 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 8
Hydrogen bond donors 6
Rotatable bonds 4
Topological polar surface area 78.66
Molecular weight 502.45
XLogP 0.22
No. Lipinski's rules broken 1
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 C1CNCCN(CCCNCCNC1)Cc1ccc(cc1)CN1CCNCCCNCCNCCC1
Isomeric SMILES C1CNCCN(CCCNCCNC1)Cc1ccc(cc1)CN1CCNCCCNCCNCCC1
InChI InChI=1S/C28H54N8/c1-9-29-15-17-31-13-3-21-35(23-19-33-11-1)25-27-5-7-28(8-6-27)26-36-22-4-14-32-18-16-30-10-2-12-34-20-24-36/h5-8,29-34H,1-4,9-26H2
InChI Key YIQPUIGJQJDJOS-UHFFFAOYSA-N
References
1. Adlere I, Sun S, Zarca A, Roumen L, Gozelle M, Viciano CP, Caspar B, Arimont M, Bebelman JP, Briddon SJ et al.. (2019)
Structure-based exploration and pharmacological evaluation of N-substituted piperidin-4-yl-methanamine CXCR4 chemokine receptor antagonists.
Eur J Med Chem, 162: 631-649. DOI: 10.1016/j.ejmech.2018.10.060 [PMID:30476826]
2. Fricker SP, Anastassov V, Cox J, Darkes MC, Grujic O, Idzan SR, Labrecque J, Lau G, Mosi RM, Nelson KL et al.. (2006)
Characterization of the molecular pharmacology of AMD3100: a specific antagonist of the G-protein coupled chemokine receptor, CXCR4.
Biochem Pharmacol, 72 (5): 588-96. [PMID:16815309]
3. Gravel S, Malouf C, Boulais PE, Berchiche YA, Oishi S, Fujii N, Leduc R, Sinnett D, Heveker N. (2010)
The peptidomimetic CXCR4 antagonist TC14012 recruits beta-arrestin to CXCR7: roles of receptor domains.
J Biol Chem, 285 (49): 37939-43. [PMID:20956518]
4. Hatse S, Princen K, Bridger G, De Clercq E, Schols D. (2002)
Chemokine receptor inhibition by AMD3100 is strictly confined to CXCR4.
FEBS Lett, 527 (1-3): 255-62. [PMID:12220670]
5. Kalatskaya I, Berchiche YA, Gravel S, Limberg BJ, Rosenbaum JS, Heveker N. (2009)
AMD3100 is a CXCR7 ligand with allosteric agonist properties.
Mol Pharmacol, 75 (5): 1240-7. [PMID:19255243]
6. Zhang WB, Navenot JM, Haribabu B, Tamamura H, Hiramatu K, Omagari A, Pei G, Manfredi JP, Fujii N, Broach JR, Peiper SC. (2002)
A point mutation that confers constitutive activity to CXCR4 reveals that T140 is an inverse agonist and that AMD3100 and ALX40-4C are weak partial agonists.
J Biol Chem, 277: 24515-24521. [PMID:11923301]