Structure Database (LMSD)

Common Name
13-hydroxy-linoleoyl-EA
Systematic Name
N-(13S-hydroxy-9Z,11E-octadecadienoyl)-ethanolamine
Synonyms
  • NAE-13-HOD
  • 13-NAE-HOD
  • 13-hydroxy-linoleoyl-ethanolamine
LM ID
LMFA08040074
Formula
C20H37NO3
Exact Mass
Calculate m/z
339.277344
Sum Composition
NAE 18:2;O
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]
Hydroxy fatty acids [FA0105]
Unsaturated fatty acids [FA0103]

References

Comments
Submitted by Omar Arias

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Arabidopsis thaliana (#3702)
Magnoliopsida (#3398)
Lipoxygenase-derived 9-hydro(pero)xides of linoleoylethanolamide interact with ABA signaling to arrest root development during Arabidopsis seedling establishment.,
Plant J, 2015
Pubmed ID: 25752187

String Representations

InChiKey (Click to copy)
GBQSRUAXKWJYGA-RKMLUMNZSA-N
InChi (Click to copy)
InChI=1S/C20H37NO3/c1-2-3-11-14-19(23)15-12-9-7-5-4-6-8-10-13-16-20(24)21-17-18-22/h7,9,12,15,19,22-23H,2-6,8,10-11,13-14,16-18H2,1H3,(H,21,24)/b9-7-,15-12+/t19-/m0/s1
SMILES (Click to copy)
C(CCCCCCC/C=C\C=C\[C@@H](O)CCCCC)(=O)NCCO

Other Databases

PubChem CID
44348037

Calculated Physicochemical Properties

Heavy Atoms 24
Rings
Aromatic Rings
Rotatable Bonds 16
Van der Waals Molecular Volume 384.01
Topological Polar Surface Area 69.56
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 4.74
Molar Refractivity 102.34

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Created at
9th Mar 2022
Updated at
7th Feb 2024