LIPID MAPS

Structure Database (LMSD)

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Common Name

20-carboxy-LTB4

Systematic Name

5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acid

Synonyms

20-carboxy-Leukotriene B4

LM ID

LMFA03020016

Formula

C₂₀H₃₀O₆

Exact Mass

Calculate m/z

366.204241

Sum Composition

FA 20:5;O4

Status

Curated

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Classification

Biological Context

20-carboxy LTB4 is a metabolite of LTB4 in human neutrophils. In human leukocytes, LTB4 is inactivated by the enzyme LTB4 20-hydroxylase. The resulting 20-hydroxy LTB4 is further oxidized to 20-carboxy LTB4.1 LTB4 metabolism in isolated rat hepatocytes also results in production of 20-carboxy LTB4 along with other ω-oxidation products.² The biological activity of 20-carboxy LTB4 is only about 2.6% compared to that of LTB4 in causing PMNL degranulation.³

This information has been provided by Cayman Chemical

References

1. Hansson, G., Lindgren, J.Å., Dahlén, S.E., et al. Identification and biological activity of novel w -oxidized metabolites of leukotriene B4 from human leukocytes. FEBS Lett. 130(1), 107-112 (1981).

2. Feinmark, S.J., Lindgren, J.Å., Claesson, H.E., et al. Stimulation of human leukocyte degranulation by leukotriene B4 and its ω-oxidized metabolites. FEBS Lett. 136, 141-144 (1981).

3. Harper, T.W., Garrity, M.J., and Murphy, R.C. Metabolism of leukotriene B4 in isolated rat hepatocytes. Identification of a novel 18-carboxy-19,20-dinor leukotriene B4 metabolite. J. Biol. Chem. 261(12), 5414-5418 (1986).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Stimulation of human leukocyte degranulation by leukotriene B4 and its omega-oxidized metabolites.,
FEBS Lett, 1981

Pubmed ID: 6274698

String Representations

InChiKey (Click to copy)

SXWGPVJGNOLNHT-VFLUTPEKSA-N

InChi (Click to copy)

InChI=1S/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/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(=O)O