LIPID MAPS

5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils by a specific dehydrogenase.¹ It stimulates cytosolic calcium levels in neutrophils with an EC50 value of 2 nM.² 5-OxoETE selectively stimulates the migration and degranulation of eosinophils and activates the MAPK pathway in stimulated neutrophils via a specific G protein-coupled receptor.^3,4,5,6

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References

1. Jones, C.E., Holden, S., Tenaillon, L., et al. Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils. Mol. Pharmacol. 63(3), 471-477 (2003).

2. Hosoi, T., Koguchi, Y., Sugikawa, E., et al. Identification of a novel human eicosanoid receptor coupled to Gi/o. J. Biol. Chem. 277 (35), 31459-31465 (2002).

3. O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes. J. Immunol. 157(1), 336-342 (1996).

4. O'Flaherty, J.T., Kuroki, M., Nixon, A.B., et al. 5-Oxo-eicosanoids and hematopoietic cytokines cooperate in stimulating neutrophil function and the mitogen-activated protein kinase pathway. J. Biol. Chem. 271(30), 17821-17828 (1996).

5. Powell, W.S., Gravelle, F., and Gravel, S. Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes. J. Biol. Chem. 267(27), 19233-19241 (1992).

6. Powell, W.S., Zhang, Y., and Gravel, S. Effects of phorbol myristate acetate on the synthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid by human polymorphonuclear leukocytes. Biochemistry 33(13), 3927-3933 (1994).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes.,
J Biol Chem, 1992

Pubmed ID: 1326548

String Representations

InChiKey (Click to copy)

MEASLHGILYBXFO-XTDASVJISA-N

InChi (Click to copy)

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+

SMILES (Click to copy)

C(O)(=O)CCCC(=O)/C=C/C=C\C/C=C\C/C=C\CCCCC