LIPID MAPS

Structure Database (LMSD)

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Common Name

5S,15S-DiHETE

Systematic Name

5S,15S-dihydroxy-6E,8Z,11Z,13E-eicosatetraenoic acid

Synonyms

LM ID

LMFA03060010

Formula

C₂₀H₃₂O₄

Exact Mass

Calculate m/z

336.23006

Sum Composition

FA 20:4;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

5(S),15(S)-DiHETE is synthesized by 15-LO from 5(S)-HETE.¹ It potentiates the degranulation of human PMNL in response to PAF, but not fMLP, calcium ionophore A23187, or LTB4.2 5(S),15(S)-DiHETE is chemotactic for eosinophils with an ED50 value of 0.3 µM.³

This information has been provided by Cayman Chemical

References

1. Morita, E., Schröder, J.M., and Christophers, E. Identification of a novel and highly potent eosinophil chemotactic lipid in human eosinophils treated with arachidonic acid. J. Immunol. 144, 1893-1900 (1990).

2. O'Flaherty, J.T., and Thomas, M.J. Effect of 15-lipoxygenase-deprived arachidonate metabolites on human neutrophil degranulation. Prostaglandins Leukot. Med. 17, 199-212 (1985).

3. Green, F.A. Transformations of 5-HETE by activated keratinocyte 15-lipoxygenase and the activation mechanism. Lipids 25, 618-623 (1990).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

UXGXCGPWGSUMNI-BVHTXILBSA-N

InChi (Click to copy)

InChI=1S/C20H32O4/c1-2-3-9-13-18(21)14-10-7-5-4-6-8-11-15-19(22)16-12-17-20(23)24/h5-8,10-11,14-15,18-19,21-22H,2-4,9,12-13,16-17H2,1H3,(H,23,24)/b7-5-,8-6-,14-10+,15-11+/t18-,19+/m0/s1

SMILES (Click to copy)

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