LIPID MAPS

Structure Database (LMSD)

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Common Name

12S-HETE

Systematic Name

12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid

Synonyms

12-HETE

LM ID

LMFA03060007

Formula

C₂₀H₃₂O₃

Exact Mass

Calculate m/z

320.235145

Sum Composition

FA 20:4;O

Status

Curated

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Classification

Biological Context

12(S)-HETE is the predominant lipoxygenase product of mammalian platelets.¹ It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix at 0.1 µM.^2,3

This information has been provided by Cayman Chemical

References

1. Honn, K.V., Nelson, K.K., Renaud, C., et al. Fatty acid modulation of tumor cell adhesion to microvessel endothelium and experimental metastasis. Prostaglandins 44(5), 413-429 (1992).

2. Grossi, I.M., Fitzgerald, L.A., Umbarger, L.A., et al. Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. Cancer Res. 49(4), 1029-1037 (1989).

3. Hamberg, M., and Samuelsson, B. Prostaglandin endoperoxides. Novel transformations of arachidonic acid in human platelets. Proc. Natl. Acad. Sci. USA 71(9), 3400-3404 (1974).

String Representations

InChiKey (Click to copy)

ZNHVWPKMFKADKW-LQWMCKPYSA-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-/m0/s1

SMILES (Click to copy)

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