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Structure Database (LMSD)

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Common Name

6-trans-LTB4

Systematic Name

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

Synonyms

6-trans-Leukotriene B4

LM ID

LMFA03020013

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 LTB4 is produced by the non-enzymatic hydrolysis of LTA4.1 Oxidative decomposition of cysteinyl-leukotrienes such as LTC4 in the presence of myeloperoxidase and hypochlorous acid can also produce 6-trans LTB4, but the physiologic importance of this mechanism is not clear.² 6-trans LTB4 is relatively inactive compared to LTB4, but chemoattractant properties in neutrophils have been reported.³

This information has been provided by Cayman Chemical

References

1. Fretland, D.J., Widomski, D.L., Anglin, C.P., et al. 6-trans-Leukotriene B4 is a neutrophil chemotoxin in the guinea pig dermis. J. Leukoc. Biol. 49, 283-288 (1991).

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, C.W., Lewis, R.A., Tauber, A.I., et al. The myeloperoxidase-dependent metabolism of leukotrienes C4, D4, and E4 to 6-trans-leukotriene B4 diastereoisomers and the subclass-specific S-diastereoisomeric sulfoxides. The Journal of Biological Chemisty 258, 15004-15010 (1983).

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-UKNWISKWSA-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-/m1/s1

SMILES (Click to copy)

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