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
References
1. Ahern GP. (2003)
Activation of TRPV1 by the satiety factor oleoylethanolamide.
J Biol Chem, 278 (33): 30429-34. [PMID:12761211]
2. Chemin J, Monteil A, Perez-Reyes E, Nargeot J, Lory P. (2001)
Direct inhibition of T-type calcium channels by the endogenous cannabinoid anandamide.
EMBO J, 20 (24): 7033-40. [PMID:11742980]
3. De Petrocellis L, Schiano Moriello A, Imperatore R, Cristino L, Starowicz K, Di Marzo V. (2012)
A re-evaluation of 9-HODE activity at TRPV1 channels in comparison with anandamide: enantioselectivity and effects at other TRP channels and in sensory neurons.
Br J Pharmacol, 167 (8): 1643-51. [PMID:22861649]
4. 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]
5. Ghafouri N, Tiger G, Razdan RK, Mahadevan A, Pertwee RG, Martin BR, Fowler CJ. (2004)
Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol.
Br J Pharmacol, 143 (6): 774-84. [PMID:15492019]
6. Maingret F, Patel AJ, Lazdunski M, Honoré E. (2001)
The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1.
EMBO J, 20 (1-2): 47-54. [PMID:11226154]
7. McHugh D, Page J, Dunn E, Bradshaw HB. (2012)
Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.
Br J Pharmacol, 165 (8): 2414-24. [PMID:21595653]
8. Mechoulam R, Ben-Shabat S, Hanus L, Ligumsky M, Kaminski NE, Schatz AR, Gopher A, Almog S, Martin BR, Compton DR et al.. (1995)
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.
Biochem Pharmacol, 50 (1): 83-90. [PMID:7605349]
9. Overton HA, Babbs AJ, Doel SM, Fyfe MC, Gardner LS, Griffin G, Jackson HC, Procter MJ, Rasamison CM, Tang-Christensen M et al.. (2006)
Deorphanization of a G protein-coupled receptor for oleoylethanolamide and its use in the discovery of small-molecule hypophagic agents.
Cell Metab, 3 (3): 167-75. [PMID:16517404]
10. Poleggi A, van der Lee S, Capellari S, Puopolo M, Ladogana A, De Pascali E, Lia D, Formato A, Bartoletti-Stella A, Parchi P et al.. (2018)
Age at onset of genetic (E200K) and sporadic Creutzfeldt-Jakob diseases is modulated by the CYP4X1 gene.
J Neurol Neurosurg Psychiatry, 89 (12): 1243-1249. [PMID:30032116]
11. Poling JS, Rogawski MA, Salem Jr N, Vicini S. (1996)
Anandamide, an endogenous cannabinoid, inhibits Shaker-related voltage-gated K+ channels.
Neuropharmacology, 35 (7): 983-91. [PMID:8938728]
12. Rajan S, Wischmeyer E, Xin Liu G, Preisig-Müller R, Daut J, Karschin A, Derst C. (2000)
TASK-3, a novel tandem pore domain acid-sensitive K+ channel. An extracellular histiding as pH sensor.
J Biol Chem, 275 (22): 16650-7. [PMID:10747866]
13. Ross RA. (2003)
Anandamide and vanilloid TRPV1 receptors.
Br J Pharmacol, 140 (5): 790-801. [PMID:14517174]
14. 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]
15. 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]
16. Smart D, Gunthorpe MJ, Jerman JC, Nasir S, Gray J, Muir AI, Chambers JK, Randall AD, Davis JB. (2000)
The endogenous lipid anandamide is a full agonist at the human vanilloid receptor (hVR1).
Br J Pharmacol, 129 (2): 227-30. [PMID:10694225]
17. Stark K, Dostalek M, Guengerich FP. (2008)
Expression and purification of orphan cytochrome P450 4X1 and oxidation of anandamide.
FEBS J, 275 (14): 3706-17. [PMID:18549450]
18. Ueda N, Yamanaka K, Yamamoto S. (2001)
Purification and characterization of an acid amidase selective for N-palmitoylethanolamine, a putative endogenous anti-inflammatory substance.
J Biol Chem, 276 (38): 35552-7. [PMID:11463796]
19. Wei BQ, Mikkelsen TS, McKinney MK, Lander ES, Cravatt BF. (2006)
A second fatty acid amide hydrolase with variable distribution among placental mammals.
J Biol Chem, 281 (48): 36569-78. [PMID:17015445]
20. Yang Z, Aubrey KR, Alroy I, Harvey RJ, Vandenberg RJ, Lynch JW. (2008)
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine.
Biochem Pharmacol, 76 (8): 1014-23. [PMID:18755158]
21. Zygmunt PM, Petersson J, Andersson DA, Chuang H, Sørgård M, Di Marzo V, Julius D, Högestätt ED. (1999)
Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide.
Nature, 400 (6743): 452-7. [PMID:10440374]