Docosahexaenoyl Ethanolamide (DHEA) is an ethanolamine amide of DHA that has been detected in both retina and brain at concentrations similar to those for arachidonoyl ethanolamide (AEA). Docosahexaenoic Acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, particularly in the retina and brain. A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets on a DHA-supplemented diet compared to a DHA-free control diet. DHEA binds rat brain CB1 receptor with a K|i|of 324 nM, which is about 10-fold higher than the K|i|for AEA. DHEA inhibits shaker-related voltage-gated potassium channels in the brain slightly better than AEA, with an IC|50|of 1.5 μM.
This compound belongs to the class of organic compounds known as n-acylethanolamines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
External Descriptors
N-acyl ethanolamines (endocannabinoids)
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Soluble in ethanol, DMSO (~20 mg/ml), DMF (~20 mg/ml), PBS (pH 7.2) (~0.15 mg/ml), and water (0.15 mg/ml at 25° C).
Índice de refracción
n20D1.52 (Predicted)
Punto de ebullición (°C)
78° C
Peso molecular
371.600 g/mol
XLogP3
5.300
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
16
Exact Mass
371.282 Da
Monoisotopic Mass
371.282 Da
Topological Polar Surface Area
49.300 Ų
Heavy Atom Count
27
Formal Charge
0
Complexity
510.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
6
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
6
Covalently-Bonded Unit Count
1
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K2209391