LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

6-trans-12-epi-LTB4

Systematic Name

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

Synonyms

6-trans-12-epi-Leukotriene B4

LM ID

LMFA03020014

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

6-trans-12-epi Leukotriene B4 (LTB4) is a non-enzymatic hydrolysis product of LTA4. It was originally isolated from glycogen-induced rabbit peritoneal polymorphonuclear leukocytes (PMNL).^1,2 6-trans-12-epi LTB4 is weakly chemotactic for PMNL, with approximately 20 times less potency than LTB4, and has no effect on the aggregation response.³

This information has been provided by Cayman Chemical

References

1. Borgeat, P., and Samuelsson, B. Arachidonic acid metabolism in polymorphonuclear leukocytes: Unstable intermediate in formation of dihydroxy acids. Proc. Natl. Acad. Sci. USA 76(7), 3213-3217 (1979).

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

3. 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).

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)

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