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Structure Database (LMSD)

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Common Name

15S-HETrE

Systematic Name

15S-hydroxy-8Z,11Z,13E-eicosatrienoic acid

Synonyms

LM ID

LMFA03050007

Formula

C₂₀H₃₄O₃

Exact Mass

Calculate m/z

322.250795

Sum Composition

FA 20:3;O

Status

Curated

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Classification

Biological Context

15(S)-HETrE is the hydroxy-trienoic acid resulting from 15-lipoxygenation of dihomo-γ-linolenic acid (DGLA). It is an inhibitor of 5-LO in human PMNL with an IC50 value of 4.6 µM.¹ In RBL cells, 15(S)-HETrE inhibits 5-LO, but is about 1/20 as potent as 15(S)-HpETE.²

This information has been provided by Cayman Chemical

References

1. Petrich, K., Ludwig, P., Kühn, H., et al. The suppression of 5-lipoxygenation of arachidonic acid in human polymorphonuclear leukocytes by the 15-lipoxygenase product (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid: Structure-activity relationship and mechanism of action. Biochem. J. 314, 911-916 (1996).

2. Haviv, F., Ratajczyk, J.D., DeNet, R.W., et al. Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues. J. Med. Chem. 30(2), 254-263 (1987).

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)

IUKXMNDGTWTNTP-OAHXIXLCSA-N

InChi (Click to copy)

InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,11-9-,17-14+/t19-/m0/s1

SMILES (Click to copy)

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