Structure Database (LMSD)

Common Name
Adrenoyl-EA
Systematic Name
N-(7Z,10Z,13Z,16Z-docosatetraenoyl)-ethanolamine
Synonyms
  • Adrenoyl-ethanolamine
LM ID
LMFA08040047
Formula
C24H41NO2
Exact Mass
Calculate m/z
375.313729
Sum Composition
NAE 22:4
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl ethanolamines (endocannabinoids) [FA0804]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

Biological Context

Docosatetraenoyl ethanolamide (DEA) is an endocannabinoid containing docosatetraenoic acid in place of the arachidonate moiety of AEA. DEA acts on CB1 receptors with potency and efficacy similar to that of AEA.1 However, its specific role and relative importance as a cannabinergic neurotransmitter have not been elucidated.2

This information has been provided by Cayman Chemical

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Sus scrofa (#9823)
Mammalia (#40674)
Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor.,
J Med Chem, 1993
Pubmed ID: 8411021

String Representations

InChiKey (Click to copy)
FMVHVRYFQIXOAF-DOFZRALJSA-N
InChi (Click to copy)
InChI=1S/C24H41NO2/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/h6-7,9-10,12-13,15-16,26H,2-5,8,11,14,17-23H2,1H3,(H,25,27)/b7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(CC(=O)NCCO)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC

Other Databases

KEGG ID
C13829
HMDB ID
HMDB0013626
CHEBI ID
34478
PubChem CID
5282273
SwissLipids ID
SLM:000598163
Cayman ID
90385
GuidePharm ID
5445

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 0
Aromatic Rings 0
Rotatable Bonds 18
Van der Waals Molecular Volume 439.14
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.59
Molar Refractivity 118.71

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Created at
-
Updated at
16th Dec 2020