Structure Database (LMSD)

Common Name
20-hydroxy-arachidic acid
Systematic Name
20-hydroxy-eicosanoic acid
Synonyms
LM ID
LMFA01050075
Formula
C20H40O3
Exact Mass
Calculate m/z
328.297746
Sum Composition
FA 20:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]

Biological Context

20-hydroxy Arachidic acid is a hydroxylated fatty acid that has been found in the suberin component of silver birch (B. pendula) outer bark as well as the leaves, roots, and wood of Q. ilex from Cala Violina and Colognole, Italy.1,2 20-hydroxy Arachidic acid was identified as a potential inhibitor of human rhinovirus coat protein in a structure-based virtual screen.3 [Matreya, LLC. Catalog No. 1877]

This information has been provided by Cayman Chemical

References

1. Karnaouri, A., Lange, H., Crestini, C., et al. Chemoenzymatic fractionation and characterization of pretreated birch outer bark. ACS Sustainable Chem. Eng. 4(10), 5289-5302 (2016).
2. Andreetta, A., Dignac, M.-F., and Carnicelli, S. Biological and physico-chemical processes influence cutin and suberin biomarker distribution in two Mediterranean forest soil profiles. Biogeochemistry 112(1-3), 41-58 (2013).
3. Rollinger, J.M., Steindl, T.M., Schuster, D., et al. Structure-based virtual screening for the discovery of natural inhibitors for human rhinovirus coat protein. J. Med. Chem. 51(4), 842-851 (2008).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Arabidopsis thaliana (#3702)
Magnoliopsida (#3398)
The lipid polyester composition of Arabidopsis thaliana and Brassica napus seeds.,
Phytochemistry, 2006
Pubmed ID: 17055542
Betula pendula (#3505)
Magnoliopsida (#3398)
Chemoenzymatic fractionation and characterization of pretreated birch outer bark,
ACS Sust Chem, 2016

String Representations

InChiKey (Click to copy)
JLDIWYKSFMPIDW-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H40O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h21H,1-19H2,(H,22,23)
SMILES (Click to copy)
C(CCCCCCCCCCO)CCCCCCCCC(=O)O

Other Databases

CHEBI ID
79190
LIPIDBANK ID
DFA0341
PubChem CID
5282919
Cayman ID
24652

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 0
Aromatic Rings 0
Rotatable Bonds 19
Van der Waals Molecular Volume 378.29
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.37
Molar Refractivity 98.32

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Created at
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Updated at
10th Apr 2025