Structure Database (LMSD)

Common Name
N-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl-EA
Systematic Name
N-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-ethanolamine
Synonyms
  • N-cis-5,8, 11,14,17-eicosapentaenoylethanolamine
  • Timnodonoyl-EA
LM ID
LMFA08040008
Formula
C22H35NO2
Exact Mass
Calculate m/z
345.266779
Sum Composition
NAE 20:5
Status
Active
Show lipids differing only in stereochemistry/bond geometry

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]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties.,
Biochim Biophys Acta, 2010
Pubmed ID: 20601112

String Representations

InChiKey (Click to copy)
OVKKNJPJQKTXIT-JLNKQSITSA-N
InChi (Click to copy)
InChI=1S/C22H35NO2/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/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
C(/C/C=C\C/C=C\C/C=C\CC)=C/C/C=C\CCCC(=O)NCCO

Other Databases

HMDB ID
HMDB0013649
CHEBI ID
71467
LIPIDBANK ID
XPR7008
PubChem CID
5283450
SwissLipids ID
SLM:000000408
Cayman ID
10964

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 401.90
Topological Polar Surface Area 49.33
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.59
Molar Refractivity 109.39

Admin

Created at
-
Updated at
7th Feb 2024