LIPID MAPS

Structure Database (LMSD)

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Common Name

9R-HODE

Systematic Name

9R-hydroxy-10E,12Z-octadecadienoic acid

Synonyms

LM ID

LMFA02000036

Formula

C₁₈H₃₂O₃

Exact Mass

Calculate m/z

296.235146

Sum Composition

FA 18:2;O

Status

Curated

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Classification

Biological Context

9(R)-HODE is a monohydroxy fatty acid and metabolite of linoleic acid .^1,2 It is formed from linoleic acid by COX and lipoxygenase (LO).^3,4 9(R)-HODE induces chemotaxis, increases the levels of chemokine (C-C motif) receptor 9 (CCR9) and chemokine (C-X-C motif) receptor 4 (CXCR4), and inhibits IL-6 release in primary human monocytes.⁵ It inhibits CD3α- and CD28-induced proliferation of isolated human peripheral blood lymphocytes when used at a concentration of 25 µg/ml.⁶

This information has been provided by Cayman Chemical

References

1. Camacho, M., Godessart, N., Anton, R., et al. Interleukin-1 enhances the ability of cultured human umbilical vein endothelial cells to oxidize linoleic acid. The Journal of Biological Chemisty 270(29), 17279-17286 (1995).

2. Kühn, H., Belkner, J., and Wiesner, R. Subcellular distribution of lipoxygenase products in rabbit reticulocyte membranes. Eur. J. Biochem. 191(1), 221-227 (1990).

3. Baer, A.N., Costello, P.B., and Green, F.A. Stereospecificity of the hydroxyeicosatetraenoic and hydroxyoctadecadienoic acids produced by cultured bovine endothelial cells. Biochim. Biophys. Acta 1085(1), 45-52 (1991).

4. Hamberg, M. Stereochemistry of oxygenation of linoleic acid catalyzed by prostaglandin-endoperoxide H synthase-2. Arch. Biochem. Biophys. 349(2), 376-380 (1998).

5. Wefers, C., Duiveman-de Boer, T., Zusterzeel, P.L.M., et al. Different lipid regulation in ovarian cancer: Inhibition of the immune system. Int. J. Mol. Sci. 19(1), 273 (2018).

6. Rolin, J., Vego, H., and Maghazachi, A.A. Oxidized lipids and lysophosphatidylcholine induce the chemotaxis, up-regulate the expression of CCR9 and CXCR4 and abrogate the release of IL-6 in human monocytes. Toxins (Basel) 6(9), 2840-2856 (2014).

String Representations

InChiKey (Click to copy)

NPDSHTNEKLQQIJ-WXUVIADPSA-N

InChi (Click to copy)

InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m0/s1

SMILES (Click to copy)

C(CCCCCCC[C@@H](O)/C=C/C=C\CCCCC)(=O)O