Structure Database (LMSD)
Common Name
Arachidonoyl amine
Systematic Name
5Z,8Z,11Z,14Z-eicosatetraenoyl amine
Synonyms
- Arachidonoylamide
3D model of Arachidonoyl amine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase (FAAH). Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase (FAAH). Arachidonoyl amide is an analog of anandamide (AEA) that lacks the hydroxyethyl moiety. It is hydrolyzed by FAAH more effectively than AEA but exhibits significantly weaker binding to the human CB1 receptor with a Ki of 9.6 µM.1,2 Arachidonoyl amide and AEA exhibit similar binding and translocation into cells via the AEA transporter. It inhibits [3H]-AEA uptake into human astrocytoma cells with an IC50 of 9 µM.3 Arachidonoyl amide also inhibits rat glial gap junction cell-cell communication by 90% at a concentration of 20 µM.4
This information has been provided by Cayman Chemical
References
4. 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).
String Representations
InChiKey (Click to copy)
BNBSCAZCQDLUDU-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C20H33NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H2,21,22)/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)N
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
22
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
361.15
Topological Polar Surface Area
43.09
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
5.62
Molar Refractivity
97.60
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Updated at
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