LIPID MAPS

12(R)-HETE is an endogenous active metabolite of the ω-6 PUFA and eicosanoid precursor arachidonic acid.^1,2 It is formed from arachidonic acid by 12R-lipoxygenase (12R-LO), as well as cytochrome P450s (CYPs). 12(R)-HETE binds to the TP receptor in washed isolated human platelets (IC50 = 0.734 µM) and inhibits platelet aggregation induced by the TP receptor agonist I-BOP (; IC50 = 3.6 µM).³ It also selectively binds to leukotriene B4 (LTB4) receptor 2 (BLT2) over BLT1 at 5 µM in CHO cell membranes expressing the human receptors.⁴ It increases the proliferation of HT-29 colon cancer cells when used at a concentration of 1 µM.⁵ 12(R)-HETE inhibits the bovine corneal Na+/K+-ATPase in a concentration-dependent manner and decreases intraocular pressure in rabbits when administered topically at doses of 1, 10, or 50 µg/eye.^6,7 Intracerebroventricular administration of 12(R)-HETE (10 µg/animal) decreases LPS-induced pyresis in rats.⁸

This information has been provided by Cayman Chemical

References

1. Mais, D.E., Saussy, D.L., Jr., Magee, D.E., et al. Interaction of 5-HETE, 12-HETE, 15-HETE and 5,12-diHETE at the human platelet thromboxane A2/prostaglandin H2 receptor. Eicosanoids 3(2), 121-124 (1990).

2. Yokomizo, T., Kato, K., Hagiya, H., et al. Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2. J. Biol. Chem. 276(15), 12454-12459 (2001).

3. Kozak, W., Kluger, M.J., Kozak, A., et al. Role of cytochrome P-450 in endogenous antipyresis. Am. J. Physiol. Regul. Integr. Comp. Physiol. 279(2), R455-R460 (2000).

4. Bortuzzo, C., Hanif, R., Kashfi, K., et al. The effect of leukotrienes B and selected HETEs on the proliferation of colon cancer cells. Biochim. Biophys. Acta 1300(3), 240-246 (1996).

5. Hawkins, D.J., and Brash, A.R. Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. J. Biol. Chem. 262(16), 7629-7634 (1987).

6. Capdevila, J., Yadagiri, P., Manna, S., et al. Absolute configuration of the hydroxyeicosatetraenoic acids (HETEs) formed during catalytic oxygenation of arachidonic acid by microsomal cytochrome P-450. Biochem. Biophys. Res. Commun. 141(3), 1007-1011 (1986).

7. Masferrer, J.L., Dunn, M.W., and Schwartzman, M.L. 12(R)-Hydroxyeicosatetraenoic acid, an endogenous corneal arachidonate metabolite, lowers intraocular pressure in rabbits. Invest. Ophthalmol. Vis. Sci. 31(3), 535-539 (1990).

8. Schwartzman, M.L., Balazy, M., Masferrer, J., et al. 12(R)-Hydroxyeicosatetraenoic acid: A cytochrome P450-dependent arachidonate metabolite that inhibits Na+,K+-ATPase in the cornea. Proc. Natl. Acad. Sci. USA 84(22), 8125-8129 (1987).

InChiKey (Click to copy)

ZNHVWPKMFKADKW-ZYBDYUKJSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m1/s1

SMILES (Click to copy)

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

KEGG ID

C14822

CHEBI ID

34144

LIPIDBANK ID

DFA8136

PubChem CID

5283156

SwissLipids ID

SLM:000389804