Structure Database (LMSD)
Common Name
Anandamide (20:4, n-6)
Systematic Name
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine
Synonyms
- Anandamide
- Anandamide(20:4, n-6)
- N-arachidonoyl ethanolamine
- arachidonoylethanolamide
- Arachidonoyl-EA
- Arachidonoyl ethanolamide
- AEA
3D model of Anandamide (20:4, n-6)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Arachidonoyl ethanolamide (AEA) is the ethanolamine amide of arachidonic acid, originally isolated from porcine brain.1 AEA is an endogenous cannabinoid neurotransmitter that binds to both cannabinoid 1 (CB1) and CB2 receptors.2 AEA has Ki values ranging from 61 to 543 nM for CB1 receptors and from 279 to 1,940 nM for CB2 receptors.3
This information has been provided by Cayman Chemical
References
1. Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258(5090), 1946-1949 (1992).
2. Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA 90(16), 7656-7660 (1993).
3. Pertwee, R.G. Pharmacology of cannabinoid receptor ligands. Curr. Med. Chem. 6(8), 635-664 (1999).
Reactions
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References
String Representations
InChiKey (Click to copy)
LGEQQWMQCRIYKG-DOFZRALJSA-N
InChi (Click to copy)
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-
SMILES (Click to copy)
C(NCCO)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR7001
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
0
Aromatic Rings
0
Rotatable Bonds
16
Van der Waals Molecular Volume
404.54
Topological Polar Surface Area
49.33
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
5.81
Molar Refractivity
109.48
Admin
Created at
-
Updated at
8th Dec 2020