LIPID MAPS

Structure Database (LMSD)

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Common Name

5-Oxo-ETE-d7

Systematic Name

5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid-d7

Synonyms

LM ID

LMFA03060083

Formula

C₂₀H₂₃D₇O₃

Exact Mass

Calculate m/z

325.263434

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

5-OxoETE-d7 contains seven deuterium atoms at the 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of 5-oxoETE by GC- or LC-mass spectrometry. 5-OxoETE is a polyunsaturated keto acid formed by the oxidation of 5-HETE in human neutrophils.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 mitogen-activated protein kinase (MAPK) pathway in stimulated neutrophils.^3,4

This information has been provided by Cayman Chemical

References

1. 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).

2. 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. The Journal of Biological Chemisty 267(27), 19233-19241 (1992).

3. 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. The Journal of Biological Chemisty 271(30), 17821-17828 (1996).

4. 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).

References

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

MEASLHGILYBXFO-BWRCDNCFSA-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+/i6D,7D,9D,10D,12D,13D,16D

SMILES (Click to copy)

C(O)(=O)CCCC(=O)/C(/[2H])=C/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\CCCCC