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
Curated
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 0
Aromatic Rings 0
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

Admin

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