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Structure Database (LMSD)

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Common Name

12-oxo-ETE

Systematic Name

12-oxo-5Z,8Z,10E,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060019

Formula

C₂₀H₃₀O₃

Exact Mass

Calculate m/z

318.219495

Sum Composition

FA 20:5;O

Status

Curated

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Classification

Biological Context

12-OxoETE is synthesized by human platelets and Aplysia nervous tissue after incubation with arachidonic acid.^1,2 Microsomal fractions of various tissues will reduce 12-oxoETE to 12(S)-HETE or a mixture of 12(S)- and 12(R)-HETE.^1,3 12-OxoETE induces a rapid, dose dependent increase of cytoplasmic free calcium via a leukotriene B4 receptor or a common activation sequence.⁴

This information has been provided by Cayman Chemical

References

1. Falgueyret, J.P., Leblanc, Y., Rokach, J., et al. NAD(P)H-dependent reduction of 12-ketoeicosatetraenoic acid to 12(R)-hydroxyeicosatetraenoic acid by rat liver microsomes. Biochem. Biophys. Res. Commun. 156, 1083-1089 (1988).

2. Fruteau De Laclos, B., Maclouf, J., Poubelle, P., et al. Conversion of arachidonic acid into 12-oxo derivatives in human platelets. A pathway possibly involving the heme-catalysed transformation of 12-hydroperoxy-eicosatetraenoic acid. Prostaglandins 33, 315-337 (1987).

3. Falgueyret, J.P., Leblanc, Y., and Riendeau, D. Stereoselective carbonyl reductases from rat skin and leukocyte microsomes converting 12-ketoeicosatetraenoic acid to 12(S)-HETE. FEBS Lett. 262, 197-200 (1990).

4. Naccache, P.H., Leblanc, Y., Rokach, J., et al. Calcium mobilization and right-angle light scatter responses to 12-oxo-derivatives of arachidonic acid in neutrophils: Evidence for the involvement of the leukotriene B4 receptor. Biochim. Biophys. Acta 1133, 102-106 (1991).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Conversion of arachidonic acid into 12-oxo derivatives in human platelets. A pathway possibly involving the heme-catalysed transformation of 12-hydroperoxy-eicosatetraenoic acid.,
Prostaglandins, 1987

Pubmed ID: 3107082

String Representations

InChiKey (Click to copy)

GURBRQGDZZKITB-VXBMJZGYSA-N

InChi (Click to copy)

InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+

SMILES (Click to copy)

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