CP55940   Click here for help

GtoPdb Ligand ID: 730

Synonyms: CP-55,940 | CP-55940 | CP55,940
PDB Ligand
Compound class: Synthetic organic
Comment: CP55940 is a synthetic, non-selective cannabinoid receptor agonist [2].
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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 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.

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Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 60.69
Molecular weight 376.3
XLogP 6.85
No. Lipinski's rules broken 1

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
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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.

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/)

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Canonical SMILES CCCCCCC(c1ccc(c(c1)O)C1CC(O)CCC1CCCO)(C)C
Isomeric SMILES CCCCCCC(c1ccc(c(c1)O)[C@@H]1C[C@H](O)CC[C@H]1CCCO)(C)C
InChI InChI=1S/C24H40O3/c1-4-5-6-7-14-24(2,3)19-11-13-21(23(27)16-19)22-17-20(26)12-10-18(22)9-8-15-25/h11,13,16,18,20,22,25-27H,4-10,12,14-15,17H2,1-3H3/t18-,20-,22-/m1/s1
InChI Key YNZFFALZMRAPHQ-SYYKKAFVSA-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. Baker D, Pryce G, Davies WL, Hiley CR. (2006)
In silico patent searching reveals a new cannabinoid receptor.
Trends Pharmacol Sci, 27 (1): 1-4. [PMID:16318877]
2. Blaazer AR, Lange JH, van der Neut MA, Mulder A, den Boon FS, Werkman TR, Kruse CG, Wadman WJ. (2011)
Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: design, synthesis, structure-activity relationships, physicochemical properties and biological activity.
Eur J Med Chem, 46 (10): 5086-98. [PMID:21885167]
3. Felder CC, Joyce KE, Briley EM, Mansouri J, Mackie K, Blond O, Lai Y, Ma AL, Mitchell RL. (1995)
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.
Mol Pharmacol, 48 (3): 443-50. [PMID:7565624]
4. Kapur A, Zhao P, Sharir H, Bai Y, Caron MG, Barak LS, Abood ME. (2009)
Atypical responsiveness of the orphan receptor GPR55 to cannabinoid ligands.
J Biol Chem, 284 (43): 29817-27. [PMID:19723626]
5. Petitet F, Donlan M, Michel A. (2006)
GPR55 as a new cannabinoid receptor: still a long way to prove it.
Chem Biol Drug Des, 67 (3): 252-3. [PMID:16611220]
6. Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG. (1999)
Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656 and AM630.
Br J Pharmacol, 126: 665-672. [PMID:10188977]
7. Ryberg E, Larsson N, Sjögren S, Hjorth S, Hermansson NO, Leonova J, Elebring T, Nilsson K, Drmota T, Greasley PJ. (2007)
The orphan receptor GPR55 is a novel cannabinoid receptor.
Br J Pharmacol, 152 (7): 1092-101. [PMID:17876302]
8. Showalter VM, Compton DR, Martin BR, Abood ME. (1996)
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.
J Pharmacol Exp Ther, 278 (3): 989-99. [PMID:8819477]