LIPID MAPS

15(R)-HETE is a monohydroxy fatty acid. It is produced by aspirin-acetylated COX-2 from arachidonic acid and converted into the specialized pro-resolving mediator 15(R)-lipoxin A4 and 15(R)-lipoxin B4 in a transcellular process via 5-lipoxygenase (5-LO).^1,2,3,4,5 It is also produced by the cytochrome P450 (CYP) isoform CYP2C9.1,2,3,6 15(R)-HETE can also be formed from arachidonic acid by COX-1 in stimulated human mast cells and accumulates because, unlike 15(S)-HETE , it is not converted to 15-KETE (15-OxoETE) by 15-hydroxyprostaglandin dehydrogenase (15-PGDH).⁷ It is an agonist of PPARβ/δ, inducing expression of a PPARβ/δ target gene in a reporter assay using NIH3T3 cells.⁸

This information has been provided by Cayman Chemical

References

1. Naruhn, S., Meissner, W., Adhikary, T., et al. 15-hydroxyeicosatetraenoic acid is a preferential peroxisome proliferator-activated receptor β/δ agonist. Mol. Pharmacol. 77(2), 171-184 (2010).

2. Bylund, J., Ericsson, J., and Oliw, E.H. Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS. Anal. Biochem. 265(1), 55-68 (1998).

3. Johnsson, A.-K., Rönnberg, E., Fuchs, D., et al. COX-1 dependent biosynthesis of 15-hydroxyeicosatetraenoic acid in human mast cells. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1866(5), 158886 (2021).

4. Schneider, C., and Brash, A.R. Stereospecificity of hydrogen abstraction in the conversion of arachidonic acid to 15R-HETE by aspirin-treated cyclooxygenase-2. Implications for the alignment of substrate in the active site. J. Biol. Chem. 275, 4743-4746 (2000).

5. Clària, J., and Serhan, C.N. Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. PNAS USA 92(21), 9475-9479 (1995).

6. Capdevila, J.H., Morrow, J.D., Belosludtsev, Y.Y., et al. The catalytic outcomes of the constitutive and the mitogen inducible isoforms of prostaglandin H2 synthase are markedly affected by glutathione and glutathione peroxidase(s). Biochemistry 34, 3325-3337 (1995).

7. Lecomte, M., Laneuville, O., Ji, C., et al. Acetylation of human prostaglandin endoperoxide synthase-2 (cyclooxygenase-2) by aspirin. J. Biol. Chem. 269(18), 13207-13215 (1994).

8. Serhan, C.N., Hamberg, M., Samuelsson, B., et al. On the stereochemistry and biosynthesis of lipoxin B. Proc. Natl. Acad. Sci. USA 83(7), 1983-1987 (1986).

InChiKey (Click to copy)

JSFATNQSLKRBCI-UDQWCNDOSA-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-/m1/s1

SMILES (Click to copy)

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

KEGG ID

C04742

HMDB ID

HMDB0062294

CHEBI ID

63989

LIPIDBANK ID

DFA8139

PubChem CID

5283169