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Structure Database (LMSD)

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Common Name

5S,12S-DiHETE

Systematic Name

5S,12S-dihydroxy-6E,8Z,10E,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060101

Formula

C₂₀H₃₂O₄

Exact Mass

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336.23006

Sum Composition

FA 20:4;O2

Status

Curated

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Classification

Biological Context

5(S),12(S)-DiHETE is a natural bioactive lipid derived from arachidonic acid (AA). It is synthesized by glycogen-induced rabbit peritoneal polymorphonuclear leukocytes (PMNLs) incubated with AA.¹ 5(S),12(S)-DiHETE can be produced by successive oxygenation of AA by 5-lipoxygenase (5-LO) in platelets and 12-LO in leukocytes.² It can also be synthesized from 12(S)-HETE by 5-LO, in the presence of 5-LO activating protein (FLAP), activated with calcium ionophore.³ 5(S),12(S)-DiHETE is an epimer of leukotriene B4 that is weakly chemotactic for PMNL.⁴

This information has been provided by Cayman Chemical

References

1. Borgeat, P., and Samuelsson, B. Metabolism of arachidonic acid in polymorphonuclear leukocytes. The Journal of Biological Chemisty 254(16), 7865-7869 (1979).

2. Lee, T.H., Mencia-Huerta, J.M., Shih, C., et al. Characterization and biologic properties of 5,12-dihydroxy derivatives of eicosapentaenoic acid, including leukotriene B5 and the double lipoxygenase product. The Journal of Biological Chemisty 259(4), 2383-2389 (1984).

3. Borgeat, P., Fruteau De Laclos, B., Picard, S., et al. Studies on the mechanism of formation of the 5S,12S-dihydroxy-6,8,10,14 (E,Z,E,Z)-eicosatetraenoic acid in leukocytes. Prostaglandins 23, 713-724 (1982).

4. Mancini, J.A., Waterman, H., and Riendeau, D. Cellular oxygenation of 12-hydroxyeicosatetraenoic acid and 15-hydroxyeicosatetraenoic acid by 5-lipoxygenase is stimulated by 5-lipoxygenase-activating protein. The Journal of Biological Chemisty 273(49), 32842-32847 (1998).

String Representations

InChiKey (Click to copy)

VNYSSYRCGWBHLG-RYYHSVJXSA-N

InChi (Click to copy)

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7-,9-6-,14-10+,15-11+/t18-,19+/m0/s1

SMILES (Click to copy)

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