Structure Database (LMSD)

Common Name
N-(19,20-epoxy-4Z,7Z,13Z,16Z-docosapentaenoyl)-EA
Systematic Name
N-(19(20)-epoxy-4Z,7Z,13Z,16Z-docosapentaenoyl)-ethanolamine
Synonyms
  • EDP-EA
LM ID
LMFA08040069
Formula
Exact Mass
Calculate m/z
387.277344
Sum Composition
Status
Curated

Classification

Biological Context

(±)19(20)-EDP ethanolamide is an ω-3 endocannabinoid epoxide and cannabinoid (CB) receptor agonist (EC50s = 108 and 280 nM for CB1 and CB2, respectively). It is produced through direct epoxygenation of docosahexaenoyl ethanolamide (DHEA) by cytochrome P450 (CYP) epoxygenases.1,2 (±)19(20)-EDP ethanolamide (25 µM) reduces the viability of 143B metastatic osteosarcoma cells.2 It decreases the production of IL-6 and increases the production of IL-10 when used at concentrations ranging from 2.5 to 10 µM in BV-2 microglia stimulated by LPS and decreases LPS-induced cytotoxicity when used at concentrations ranging from 5 to 10 µM. It also decreases nitrite production when used at a concentration of 7.5 µM, an effect that can be partially reversed by the CB2 receptor antagonist AM630 and the PPARγ antagonist GW 9662 . (±)19(20)-EDP ethanolamide induces vasodilation of isolated preconstricted bovine coronary arteries (ED50 = 1.9 µM) and reduces tube formation by human microvascular endothelial cells (HMVECs) in a Matrigel™ assay.

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Anti-inflammatory omega-3 endocannabinoid epoxides.,
Proc Natl Acad Sci U S A,, 2017
Pubmed ID: 28687674

String Representations

InChiKey (Click to copy)
HQRHKQCFLLFLJV-MBYQGORISA-N
InChi (Click to copy)
InChI=1S/C24H37NO3/c1-2-22-23(28-22)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-24(27)25-20-21-26/h3-4,7-10,13-16,22-23,26H,2,5-6,11-12,17-21H2,1H3,(H,25,27)/b4-3-,9-7-,10-8-,15-13-,16-14-
SMILES (Click to copy)
C(/C/C=C\C/C=C\C/C=C\CC1OC1CC)=C/C/C=C\CCC(=O)NCCO

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 1
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 432.93
Topological Polar Surface Area 61.86
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 5.93
Molar Refractivity 119.07

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Created at
25th Nov 2020
Updated at
7th Feb 2024