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Structure Database (LMSD)

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Common Name

5S,6R-DiHETE

Systematic Name

5S,6R-dihydroxy-7E,9E,11Z,14Z-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060017

Formula

C₂₀H₃₂O₄

Exact Mass

Calculate m/z

336.23006

Sum Composition

FA 20:4;O2

Status

Curated

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Classification

Biological Context

5(S),6(R)-DiHETE is a dihydroxy polyunsaturated fatty acid and a nonenzymatic hydrolysis product of leukotriene A4 (LTA4). Mouse liver cytosolic epoxide hydrolase catalyzes the conversion of LTA4 to 5(S),6(R)-DiHETE.¹ It is a weak LTD4 receptor agonist in guinea pig lung membranes.² It induces guinea pig ileum contraction with an ED50 value of 1.3 µM.²

This information has been provided by Cayman Chemical

References

1. Muller, A., Rechencq, E., Kugel, C., et al. Comparative biological activities of the four synthetic (5,6)-diHETE isomers. Prostaglandins 38(6), 635-644 (1989).

2. Haeggström, J., Wetterholm, A., Hamberg, M., et al. Enzymatic formation of 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid: Kinetics of the reaction and stereochemistry of the product. Biochim. Biophys. Acta. 958(3), 469-476 (1988).

String Representations

InChiKey (Click to copy)

UVZBUUTTYHTDRR-NSEFZGNTSA-N

InChi (Click to copy)

InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-13,15,18-19,21-22H,2-5,8,14,16-17H2,1H3,(H,23,24)/b7-6-,10-9-,12-11+,15-13+/t18-,19+/m1/s1

SMILES (Click to copy)

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