LIPID MAPS

Structure Database (LMSD)

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Common Name

LTB4

Systematic Name

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

Synonyms

Leukotriene B4
5S,12R-diHETE

LM ID

LMFA03020001

Formula

C₂₀H₃₂O₄

Exact Mass

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336.230061

Sum Composition

FA 20:4;O2

Status

Curated

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Classification

Biological Context

Leukotriene B4 (LTB4) is a dihydroxy fatty acid derived from arachidonic acid through the 5-LO pathway.^1,2,3 It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. In subnanomolar ranges (3.9 x 10−10 M), LTB4 causes chemotaxis and chemokinesis in human polymorphonuclear leukocytes.⁴ At higher concentrations, (1.0 x 10−7 M), LTB4 leads to neutrophil aggregation and degranulation as well as superoxide anion production.^4,5

This information has been provided by Cayman Chemical

References

2. Ford-Hutchinson, A.W., Bray, M.A., Doig, M.V., et al. Leukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes. Nature 286(5770), 264-265 (1980).

3. Rådmark, O., Malmsten, C., Samuelsson, B., et al. Leukotriene A: Stereochemistry and enzymatic conversion to leukotriene B. Biochem. Biophys. Res. Commun. 92(3), 954-961 (1980).

4. Ford-Hutchinson, A.W. Leukotriene B4 in inflammation. Crit. Rev. Immunol. 10(1), 1-12 (1990).

1. McGee, J., and Fitzpatrick, F. Enzymatic hydration of leukotriene A4. Purification and characterization of a novel epoxide hydrolase from human erythrocytes. J. Biol. Chem. 260(23), 12832-12837 (1985).

5. McMillan, R.M., and Foster, S.J. Leukotriene B4 and inflammatory disease. Agents Actions 24(1-2), 114-119 (1988).

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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

Homo sapiens (#9606)

Mammalia (#40674)

Leukotriene B. Total synthesis and assignment of stereochemistry,
J Am Chem Soc, 1980

DOI: 10.1021/ja00547a051

String Representations

InChiKey (Click to copy)

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