Structure Database (LMSD)

OH O N H
Common Name
N-(5Z,8Z,11Z-eicosatrienoyl)-EA
Systematic Name
N-(5Z,8Z,11Z-eicosatrienoyl)-ethanolamine
Synonyms
  • Mead ethanolamide
  • Mead Acid-EA
LM ID
LMFA08040037
Formula
C22H39NO2
Exact Mass
Calculate m/z
349.298079
Sum Composition
NAE 20:3
Status
Active
Show lipids differing only in stereochemistry/bond geometry
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Main

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]

String Representations

InChiKey (Click to copy)
YKGQBEGMUSSPFY-YOILPLPUSA-N
InChi (Click to copy)
InChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h9-10,12-13,15-16,24H,2-8,11,14,17-21H2,1H3,(H,23,25)/b10-9-,13-12-,16-15-
SMILES (Click to copy)
C(CCC/C=C\C/C=C\C/C=C\CCCCCCCC)(=O)NCCO

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Mead ethanolamide, a novel eicosanoid, is an agonist for the central (CB1) and peripheral (CB2) cannabinoid receptors.,
Mol Pharmacol, 1995
Pubmed ID: 7651362

Other Databases

CHEBI ID
165588
PubChem CID
16061185
Cayman ID
90195

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 17
Van der Waals Molecular Volume 407.18
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.03
Molar Refractivity 109.57

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Created at
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Updated at
7th Feb 2024