JNJ-47965567   Click here for help

GtoPdb Ligand ID: 7538

Synonyms: JNJ-479655 | JNJ47965567
PDB Ligand
Compound class: Synthetic organic
Comment: JNJ-479655 is a centrally acting, selective P2X7 antagonist. The enhanced brain to plasma ratio achieved by this compound boosts its utility as a tool to understand the role of P2X7 in CNS models of pathophysiology [1].
Click here for help

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.

✖

View interactive charts of activity data across species

JNJ-47965567 is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 6
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 83
Molecular weight 488.22
XLogP 4.59
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES O=C(c1cccnc1Sc1ccccc1)NCC1(CCOCC1)N1CCN(CC1)c1ccccc1
Isomeric SMILES O=C(c1cccnc1Sc1ccccc1)NCC1(CCOCC1)N1CCN(CC1)c1ccccc1
InChI InChI=1S/C28H32N4O2S/c33-26(25-12-7-15-29-27(25)35-24-10-5-2-6-11-24)30-22-28(13-20-34-21-14-28)32-18-16-31(17-19-32)23-8-3-1-4-9-23/h1-12,15H,13-14,16-22H2,(H,30,33)
InChI Key XREFXUCWSYMIOG-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Bhattacharya A, Wang Q, Ao H, Shoblock JR, Lord B, Aluisio L, Fraser I, Nepomuceno D, Neff RA, Welty N et al.. (2013)
Pharmacological characterization of a novel centrally permeable P2X7 receptor antagonist: JNJ-47965567.
Br J Pharmacol, 170 (3): 624-40. [PMID:23889535]
2. Chessell IP, Hatcher JP, Bountra C, Michel AD, Hughes JP, Green P, Egerton J, Murfin M, Richardson J, Peck WL, Grahames CB, Casula MA, Yiangou Y, Birch R, Anand P, Buell GN. (2005)
Disruption of the P2X7 purinoceptor gene abolishes chronic inflammatory and neuropathic pain.
Pain, 114 (3): 386-96. [PMID:15777864]
3. Diaz-Hernandez JI, Gomez-Villafuertes R, León-Otegui M, Hontecillas-Prieto L, Del Puerto A, Trejo JL, Lucas JJ, Garrido JJ, Gualix J, Miras-Portugal MT et al.. (2012)
In vivo P2X7 inhibition reduces amyloid plaques in Alzheimer's disease through GSK3β and secretases.
Neurobiol Aging, 33 (8): 1816-28. [PMID:22048123]
4. Engel T, Gomez-Villafuertes R, Tanaka K, Mesuret G, Sanz-Rodriguez A, Garcia-Huerta P, Miras-Portugal MT, Henshall DC, Diaz-Hernandez M. (2012)
Seizure suppression and neuroprotection by targeting the purinergic P2X7 receptor during status epilepticus in mice.
FASEB J, 26 (4): 1616-28. [PMID:22198387]
5. Iwata M, Ota KT, Duman RS. (2013)
The inflammasome: pathways linking psychological stress, depression, and systemic illnesses.
Brain Behav Immun, 31: 105-14. [PMID:23261775]
6. Jones KA, Thomsen C. (2013)
The role of the innate immune system in psychiatric disorders.
Mol Cell Neurosci, 53: 52-62. [PMID:23064447]
7. Khakh BS, North RA. (2012)
Neuromodulation by extracellular ATP and P2X receptors in the CNS.
Neuron, 76 (1): 51-69. [PMID:23040806]
8. Khansari PS, Sperlagh B. (2012)
Inflammation in neurological and psychiatric diseases.
Inflammopharmacology, 20 (3): 103-7. [PMID:22361843]
9. North RA, Jarvis MF. (2013)
P2X receptors as drug targets.
Mol Pharmacol, 83 (4): 759-69. [PMID:23253448]
10. Sharp AJ, Polak PE, Simonini V, Lin SX, Richardson JC, Bongarzone ER, Feinstein DL. (2008)
P2x7 deficiency suppresses development of experimental autoimmune encephalomyelitis.
J Neuroinflammation, 5: 33. [PMID:18691411]