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Structure Database (LMSD)

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Common Name

Cervonoyl-EA

Systematic Name

N-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-ethanolamine

Synonyms

N-cis-4,7,10,13,16,19-docosahexanoylethanolamine
Synaptamide
DEA

LM ID

LMFA08040009

Formula

C₂₄H₃₇NO₂

Exact Mass

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371.282429

Sum Composition

NAE 22:6

Status

Curated

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Classification

Biological Context

Docosahexaenoyl ethanolamide (DHEA) is the ethanolamine amide of DHA that has been detected in both brain and retina at concentrations similar to those for arachidonoyl ethanolamide (AEA).^1,2 A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets fed a diet supplemented with docosahexaenoic acid (DHA) compared to a control diet without DHA.³ DHEA binds to the rat brain CB1 receptor with a Ki of 324 nM, which is approximately 10-fold higher than the Ki for AEA.⁴ DHEA inhibits shaker-related voltage-gated potassium channels in brain slightly better than AEA, with an IC50 of 1.5 µM.⁵

This information has been provided by Cayman Chemical

References

1. Sugiura, T., Kondo, S., Sukagawa, A., et al. Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonoylethanolamine, an endogenous cannabinoid-receptor ligand, in rat brain microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine. Eur. J. Biochem. 240, 53-62 (1996).

2. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J. Med. Chem. 40(5), 659-667 (1997).

3. Bisogno, T., Delton-Vandenbroucke, I., Milone, A., et al. Biosynthesis and inactivation of N-Arachidonoylethanolamine (Ananadamide) and N-Docosahexaenoylethanolamine in bovine retina. Arch. Biochem. Biophys. 370(2), 300-307 (1999).

4. Poling, J.S., Rogawski, M.A., Salem, N., Jr., et al. Anadamide, an endogenous cannabinoid, inhibits shaker-related voltage-gated K+ channels. Neuropharmacology 35(7), 983-991 (1996).

5. Berger, A., Crozier, G., Bisogno, T., et al. Anandamide and diet: Inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N-acylethanolamines in piglets. Proc. Natl. Acad. Sci. USA 98(11), 6402-6406 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Mus musculus (#10090)

Mammalia (#40674)

A synaptogenic amide N-docosahexaenoylethanolamide promotes hippocampal development.,
Prostaglandins Other Lipid Mediat, 2011

Pubmed ID: 21810478

String Representations

InChiKey (Click to copy)

GEEHOLRSGZPBSM-KUBAVDMBSA-N

InChi (Click to copy)

InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

SMILES (Click to copy)

C(/C/C=C\C/C=C\C/C=C\C/C=C\CC)=C/C/C=C\CCC(=O)NCCO