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
3D model of N-(19,20-epoxy-4Z,7Z,13Z,16Z-docosapentaenoyl)-EA
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
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
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
Admin
Created at
25th Nov 2020
Updated at
7th Feb 2024