Structure Database (LMSD)

Common Name
Arachidonoyl amine
Systematic Name
5Z,8Z,11Z,14Z-eicosatetraenoyl amine
Synonyms
  • Arachidonoylamide
LM ID
LMFA08010007
Formula
Exact Mass
Calculate m/z
303.256214
Status
Curated

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

CHEBI ID
PubChem CID
Cayman ID

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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