[3H]rimonabant   Click here for help

GtoPdb Ligand ID: 745

Synonyms: [3H]-rimonabant | [3H]-SR141716 | [3H]SR141716A
 Ligand is labelled  Ligand is radioactive
Compound class: Synthetic organic
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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 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 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 49.64
Molecular weight 462.08
XLogP 6.13
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 Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
Isomeric SMILES Clc1ccc(cc1)c1n(nc(c1C([3H])([3H])[3H])C(=O)NN1CCCCC1)c1ccc(cc1Cl)Cl
InChI InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)/i1T3
InChI Key JZCPYUJPEARBJL-RLXJOQACSA-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. Breivogel CS, Sim LJ, Childers SR. (1997)
Regional differences in cannabinoid receptor/G-protein coupling in rat brain.
J Pharmacol Exp Ther, 282 (3): 1632-42. [PMID:9316881]
2. Hirst RA, Almond SL, Lambert DG. (1996)
Characterisation of the rat cerebella CB1 receptor using SR141716A, a central cannabinoid receptor antagonist.
Neurosci Lett, 220 (2): 101-4. [PMID:8981483]
3. Jung M, Calassi R, Rinaldi Carmona M, Chardenot P, Le Fur G, Soubrie P, Oury-Donat F. (1997)
Characterization of CB1 receptors on rat neuronal cell cultures: binding and functional studies using the selective receptor antagonist SR 141716A.
J Neurochem, 68: 402-409. [PMID:8978752]
4. Petitet F, Marin L, Doble A. (1996)
Biochemical and pharmacological characterization of cannabinoid binding sites using [3H]SR141716A.
Neuroreport, 7: 789-792. [PMID:8733746]
5. Rinaldi-Carmona M, Pialot F, Congy C, Redon E, Barth F, Bachy A, Breliere JC, Soubrie P, Le Fur G. (1996)
Characterization and distribution of binding sites for [3H]-SR 141716A, a selective brain (CB1) cannabinoid receptor antagonist, in rodent brain.
Life Sci, 58: 1239-1247. [PMID:8614277]
6. 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]
7. Sim LJ, Hampson RE, Deadwyler SA, Childers SR. (1996)
Effects of chronic treatment with delta9-tetrahydrocannabinol on cannabinoid-stimulated [35S]GTPgammaS autoradiography in rat brain.
J Neurosci, 16 (24): 8057-66. [PMID:8987831]
8. Thomas BF, Gilliam AF, Burch DF, Roche MJ, Seltzman HH. (1998)
Comparative receptor binding analyses of cannabinoid agonists and antagonists.
J Pharmacol Exp Ther, 285 (1): 285-92. [PMID:9536023]