anandamide   Click here for help

GtoPdb Ligand ID: 2364

Synonyms: AEA | arachidonoyl ethanolamide | N-arachidonoylethanolamine
PDB Ligand
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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2D Structure
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Physico-chemical Properties
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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
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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-
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]