LIPID MAPS

15(S)-HETE is an active metabolite of arachidonic acid .¹ It is formed via oxidation of arachidonic acid by 15-lipoxygenase 2 (15-LO-2) in macrophages, as well as the prostate, lung, and skin, but also by 15-LO-1 in airway epithelial cells, eosinophils, and reticulocytes.^2,3 15(S)-HETE inhibits the proliferation of HT-29 colorectal and PC3 prostate cancer cells (IC50s = 40 and 30 µM, respectively).^4,5 It increases kruppel-like factor 10 (KLF10) and decreases B cell lymphoma 2 (Bcl-2) protein levels in HT-29 cells when used at a concentration of 40 µM.⁴ 15(S)-HETE (0.1 µM) increases HMG-CoA reductase protein levels in human dermal microvascular endothelial cells (HDMVECs).⁶ It increases Rac1 protein levels and induces farnesylation of Rac1 in HDMVECs when used at a concentration of 0.1 µM.

This information has been provided by Cayman Chemical

References

1. Chen, G.G., Xu, H., Lee, J.F.Y., et al. 15-Hydroxy-eicosatetraenoic acid arrests growth of colorectal cancer cells via a peroxisome proliferator-activated receptor gamma-dependent pathway. Int. J. Cancer 107(5), 837-843 (2003).

2. Singh, N.K., Kundumani-Sridharan, V., and Rao, G.N. 12/15-Lipoxygenase gene knockout severely impairs ischemia-induced angiogenesis due to lack of Rac1 farnesylation. Blood 118(20), 5701-5712 (2011).

3. Yuan, H., Li, M.-Y., Ma, L.T., et al. 15-Lipoxygenases and its metabolites 15(S)-HETE and 13(S)-HODE in the development of non-small cell lung cancer. Thorax. 65(4), 321-326 (2010).

4. Powell, W.S., and Rokach, J. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochim. Biophys. Acta 1851(4), 340-355 (2014).

5. Shappell, S.B., Gupta, R.A., Manning, S., et al. 15S-hydroxyeicosatetraenoic acid activates peroxisome proliferator-activated receptor γ and inhibits proliferation in PC3 prostate carcinoma cells. Cancer Res. 61, 497-503 (2001).

6. Nadel, J.A., Conrad, D.J., Ueki, I.F., et al. Immunocytochemical localization of arachidonate 15-lipoxygenase in erythrocyes, leukocytes, and airway cells. J. Clin. Invest. 87(4), 1139-1145 (1991).

InChiKey (Click to copy)

JSFATNQSLKRBCI-VAEKSGALSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

SMILES (Click to copy)

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

KEGG ID

C04742

HMDB ID

HMDB0003876

CHEBI ID

15558

LIPIDBANK ID

DFA8140

PubChem CID

5280724