Structure Database (LMSD)

Common Name
9-hydroxy-linoleoyl-EA
Systematic Name
N-(9S-hydroxy-10E,12Z-octadecadienoyl)-ethanolamine
Synonyms
  • NAE-9-HOD
  • 9-NAE-HOD
  • 9-hydroxy-linoleoylethanolamide
LM ID
LMFA08040075
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)
VYCHZJQSKAOAAT-UGGXVOJLSA-N
InChi (Click to copy)
InChI=1S/C20H37NO3/c1-2-3-4-5-6-8-11-14-19(23)15-12-9-7-10-13-16-20(24)21-17-18-22/h6,8,11,14,19,22-23H,2-5,7,9-10,12-13,15-18H2,1H3,(H,21,24)/b8-6-,14-11+/t19-/m1/s1
SMILES (Click to copy)
C(CCCCCCC[C@H](O)/C=C/C=C\CCCCC)(=O)NCCO

Other Databases

PubChem CID
171119164

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