anandamide   Click here for help

GtoPdb Ligand ID: 2364

Synonyms: AEA | arachidonoyl ethanolamide | N-arachidonoylethanolamine
PDB Ligand
Compound class: Metabolite or derivative
Comment: Anandamide is an endogenous cannabinoid neurotransmitter found in animal and human organs, especially in the brain. It activates the cannabinoid receptors CB1 and CB2. Anandamide is also known to be an endogenous activator of the TRPV1 cation channel [3,13], which is involved in regulation of body temperature and nociception.
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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

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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 3
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 49.33
Molecular weight 347.28
XLogP 7.43
No. Lipinski's rules broken 2
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 CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO
InChI InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-
InChI Key LGEQQWMQCRIYKG-DOFZRALJSA-N
Natural/Endogenous Targets
Target
CB1 receptor
CB2 receptor
GPR55
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
monoacylglycerol lipase 5
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CB1 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 6.3 – 7.0 pKi - 4,15
⤷ pKi 6.3 – 7.0 [4,15]
CB2 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 5.7 – 6.4 pKi - 4,8,15
⤷ pKi 5.7 – 6.4 [4,8,15]
GPR55 Ligand is endogenous in the given species Hs Agonist Agonist 7.7 pEC50 - 14
⤷ pEC50 7.7 (EC50 1.8x10-8 M) [14]
GPR18 Hs Agonist Full agonist 5.4 pEC50 - 7
⤷ pEC50 5.4 (EC50 3.83x10-6 M) [7]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
glycine receptor α1 subunit Hs Allosteric modulator Potentiation 7.4 pEC50 -
⤷ pEC50 7.4 (EC50 3.8x10-8 M)
Glycine Receptor (All subtypes) N/A Subunit-specific Potentiation 7.2 pEC50 < 1x10-8 20
⤷ pEC50 7.2 Conc range: < 1x10-8 M α1 and α1β only, no effect on α2 or α3 [20]
TRPV1 Ligand is endogenous in the given species Hs Activator Agonist 5.9 pEC50 - 16
⤷ pEC50 5.9 [16]
Voltage: -70.0 mV
TRPV1 Ligand is endogenous in the given species Rn Activator Agonist 5.3 pEC50 - 21
⤷ pEC50 5.3 [21]
Voltage: -40.0 mV
TRPV1 Ligand is endogenous in the given species Hs Activator Activation 5.0 pEC50 - 1
⤷ pEC50 5.0 [1]
Cav3.2 Ligand is endogenous in the given species Hs Channel blocker Antagonist 6.5 pIC50 - 2
⤷ pIC50 6.5 [2]
Voltage: -80.0 mV
K2P3.1 Hs Channel blocker - ~6.2 pIC50 - 6
⤷ pIC50 ~6.2 (IC50 ~7x10-7 M) [6]
Cav3.3 Hs Channel blocker Antagonist 6.0 pIC50 - 2
⤷ pIC50 6.0 [2]
Voltage: -80.0 mV
K2P3.1 Hs Channel blocker Inhibition 5.6 pIC50 - 6
⤷ pIC50 5.6 (IC50 2.7x10-6 M) [6]
Kv1.2 Hs Channel blocker Pore blocker 5.6 pIC50 - 11
⤷ pIC50 5.6 (IC50 2.7x10-6 M) [11]
Cav3.1 Ligand is endogenous in the given species Hs Channel blocker Antagonist 5.4 pIC50 - 2
⤷ pIC50 5.4 [2]
Voltage: -80.0 mV
TRPM8 Hs Channel blocker - - - -
⤷
K2P9.1 Hs Inhibitor - - - - 12
⤷ studied at 1-10 µM [12]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Rank order of affinity at Fatty acid amide hydrolase anandamide > oleamide > N-oleoylethanolamide > N-palmitoylethanolamine 19
Rank order of affinity at Fatty acid amide hydrolase-2 oleamide > N-oleoylethanolamide > anandamide > N-palmitoylethanolamine 19
Rank order of affinity at N-Acylethanolamine acid amidase N-palmitoylethanolamine > MEA > SEA ≥ N-oleoylethanolamide > anandamide 18
Endogenous substrates at monoacylglycerol lipase 2-oleoyl glycerol = 2-arachidonoylglycerol >> anandamide 5
Potency order of endogenous ligands at GPR119 N-oleoylethanolamide, N-palmitoylethanolamine > SEA (anandamide is ineffective) 9
Targets where the ligand is described in the comment field
Target Comment
CYP4X1 Converts anandamide to 14,15-epoxyeicosatrienoic ethanolamide [17]. May influence age of onset of sporadic Creutzfeldt-Jakob diseases [10].
Ligand mentioned in the following text fields
Cannabinoid receptors overview
Endocannabinoid turnover overview
Cannabinoid receptors comments
Glycine transporter subfamily comments
Phosphatidylcholine-specific phospholipase D comments
Transient Receptor Potential channels (TRP) comments