Structure Database (LMSD)

Common Name
2-HOTrE
Systematic Name
2-hydroxy-9Z,12Z,15Z-octadecatrienoic acid
Synonyms
  • alpha-Hydroxy-alpha-linolenic acid
  • alpha-Hydroxylinolenic acid
LM ID
LMFA02000183
Formula
C18H30O3
Exact Mass
Calculate m/z
294.219495
Sum Composition
FA 18:3;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
Other Octadecanoids [FA0200]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

Biological Context

(±)2-HOTrE is an oxylipin.1 It is active against the plant pathogenic fungi A. niger, S. cerevisiae, and P. membranae-faciens (MICs = 1.5, 3, and 1 g/L, respectively), as well as P. roqueforti, C. albicans, and C. valida (MICs = 2.33, 3, and 2 g/L, respectively). Hepatic levels of 2-HOTrE are increased in a mouse model of non-alcoholic fatty liver disease (NAFLD) induced by a high-fat diet.2

This information has been provided by Cayman Chemical

References

1. Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).
2. Liang, N., Dacko, A., Tan, A.K., et al. Structure-function relationships of antifungal monohydroxy unsaturated fatty acids (HUFA) of plant and bacterial origin. Food Res. Int. 134, 109237 (2020).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Salvia nilotica (#268918)
Magnoliopsida (#3398)
Unsaturated C18 alpha-hydroxy acids in Salvia nilotica,
Lipids, 1975

String Representations

InChiKey (Click to copy)
JQXGCBKGIBTCHY-PDBXOOCHSA-N
InChi (Click to copy)
InChI=1S/C18H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h3-4,6-7,9-10,17,19H,2,5,8,11-16H2,1H3,(H,20,21)/b4-3-,7-6-,10-9-
SMILES (Click to copy)
C(C(O)CCCCCC/C=C\C/C=C\C/C=C\CC)(=O)O

Other Databases

LIPIDAT ID
4835
CHEBI ID
165778
PubChem CID
5312775
PlantFA ID
10409
Cayman ID
39100

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 335.77
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.92
Molar Refractivity 88.80

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Created at
-
Updated at
1st Jun 2023