Structure Database (LMSD)

Common Name
Dihomo-alpha-linolenoyl-EA
Systematic Name
N-(11Z,14Z,17Z-eicosatrienoyl)-ethanolamine
Synonyms
  • N-cis-11, 14,17-eicosatrienoylethanolamine
  • Dihomo-alpha-linolenoyl ethanolamide
LM ID
LMFA08040005
Formula
C22H39NO2
Exact Mass
Calculate m/z
349.298079
Sum Composition
NAE 20:3
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
synthetic construct (#32630)
Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.,
J Med Chem, 1997
Pubmed ID: 9057852

String Representations

InChiKey (Click to copy)
IGERBKTWMBMXMC-PDBXOOCHSA-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/h3-4,6-7,9-10,24H,2,5,8,11-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-
SMILES (Click to copy)
C(C/C=C\C/C=C\C/C=C\CC)CCCCCCCC(=O)NCCO

Other Databases

CHEBI ID
165578
LIPIDBANK ID
XPR7005
PubChem CID
5283447
SwissLipids ID
SLM:000598138

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
-
Updated at
7th Feb 2024