nabilone   Click here for help

GtoPdb Ligand ID: 9071

Synonyms: Cesamet® | LY 109514 | LY-109514
Approved drug
nabilone is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: Nabilone is a synthetic cannabinoid, used as an anti-emetic drug. It is a mixture of enantiomers. We show the 'flat' molecule with no specified stereochemistry to represent the mixture.
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: nabilone

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 1
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 46.53
Molecular weight 372.27
XLogP 6.8
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 CCCCCCC(c1cc(O)c2c(c1)OC(C1C2CC(=O)CC1)(C)C)(C)C
Isomeric SMILES CCCCCCC(c1cc(O)c2c(c1)OC(C1C2CC(=O)CC1)(C)C)(C)C
InChI InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3
InChI Key GECBBEABIDMGGL-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1985))
IUPAC Name Click here for help
1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
International Nonproprietary Names Click here for help
INN number INN
3930 nabilone
Synonyms Click here for help
Cesamet® | LY 109514 | LY-109514
Database Links Click here for help
Specialist databases
GPCRdb Ligand nabilone
Other databases
ChEMBL Ligand CHEMBL2218896
DrugCentral Ligand 1862
GtoPdb PubChem SID 315661156
PubChem CID 39860
Search Google for chemical match using the InChIKey GECBBEABIDMGGL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GECBBEABIDMGGL
Search PubMed clinical trials nabilone
Search PubMed titles nabilone
Search PubMed titles/abstracts nabilone
UniChem Compound Search for chemical match using the InChIKey GECBBEABIDMGGL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GECBBEABIDMGGL-UHFFFAOYSA-N
Wikipedia Nabilone