LIPID MAPS

Structure Database (LMSD)

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Common Name

4-oxo DHA

Systematic Name

4-oxo-5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid

Synonyms

4-oxo Docosahexaenoic Acid

LM ID

LMFA02000484

Formula

C₂₂H₃₀O₃

Exact Mass

Calculate m/z

342.219496

Sum Composition

FA 22:7;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

4-oxo Docosahexaenoic acid is an active metabolite of docosahexaenoic acid.¹ It is formed from docosahexaenoic acid by 5-lipoxygenase (5-LO). 4-oxo Docosahexaenoic acid is an agonist of peroxisome proliferator-activated receptor γ (PPARγ).² It induces gene transcription in a reporter assay using COS-1 cells expressing PPARγ (EC50 = ~10 µM). 4-oxo Docosahexaenoic acid (100 µM) decreases the proliferation of MDA-MB-231, BT-549, T47D, and SK-BR-3 breast cancer cells, MCF-10F breast epithelial cells, and increases the proliferation of MCF-7 breast cancer cells.³

This information has been provided by Cayman Chemical

References

1. Chen, K.-M., Thompson, H., Vanden-Heuvel, J.P., et al. Lipoxygenase catalyzed metabolites derived from docosahexaenoic acid are promising antitumor agents against breast cancer. Sci. Rep. 11(1), 410 (2021).

2. Itoh, T., Fairall, L., Amin, K., et al. Structural basis for the activation of PPARγ by oxidized fatty acids. Nat. Struct. Mol. Biol. 15(9), 924-931 (2008).

3. Pogash, T.J., El-Bayoumy, K., Amin, S., et al. Oxidized derivative of docosahexaenoic acid preferentially inhibit cell proliferation in triple negative over luminal breast cancer cells. In Vitro Cell. Dev. Biol. Anim. 51(2), 121-127 (2015).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Oxidized derivative of docosahexaenoic acid preferentially inhibit cell proliferation in triple negative over luminal breast cancer cells.,
In Vitro Cell Dev Biol Anim, 2015

Pubmed ID: 25413005

String Representations

InChiKey (Click to copy)

UHNUULCIKILOHW-PQVBWYSWSA-N

InChi (Click to copy)

InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(23)19-20-22(24)25/h3-4,6-7,9-10,12-13,15-18H,2,5,8,11,14,19-20H2,1H3,(H,24,25)/b4-3-,7-6-,10-9-,13-12-,16-15-,18-17+

SMILES (Click to copy)

C(CCC(=O)/C=C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O