LIPID MAPS

Structure Database (LMSD)

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Common Name

Lipoxin A4

Systematic Name

5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid

Synonyms

LXA4
5S,6R-LipoxinA4

LM ID

LMFA03040001

Formula

C₂₀H₃₂O₅

Exact Mass

Calculate m/z

352.224975

Sum Composition

FA 20:4;O3

Status

Curated

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Classification

Biological Context

Lipoxin A4 (LXA4) is a trihydroxy fatty acid containing a conjugated tetraene, produced by the metabolism of (±)15-HETE or 15-HpETE with human leukocytes.¹ LXA4 is equipotent to leukotriene B4 in inducing superoxide generation in human neutrophils at 0.1 µM.² LXA4 is associated with several other biological functions including leukocyte activation, chemotaxis effects, natural killer cell inhibition, and monocyte migration and adhesion.^2,3,4

This information has been provided by Cayman Chemical

References

1. Serhan, C.N., Hamberg, M., and Samuelsson, B. Lipoxins: Novel series of biologically active compounds formed from arachidonic acid in human leukocytes. Proc. Natl. Acad. Sci. USA 81(17), 5335-5339 (1984).

2. Serhan, C.N., Nicolaou, K.C., Webber, S.E., et al. Lipoxin A. Stereochemistry and biosynthesis. The Journal of Biological Chemisty 261(35), 16340-16345 (1986).

3. Ramstedt, U., Serhan, C.N., Nicolaou, K.C., et al. Lipoxin A-induced inhibition of human natural killer cell cytotoxicity: Studies on stereospecificity of inhibition and mode of action. J. Immunol. 138(1), 266-270 (1987).

4. Maddox, J.F., and Serhan, C.N. Lipoxin A4 and B4 are potent stimuli for human monocyte migration and adhesion: Selective inactivation by dehydrogenation and reduction. J. Exp. Med. 183(1), 137-146 (1996).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipoxin A. Stereochemistry and biosynthesis.,
J Biol Chem, 1986

Pubmed ID: 3097008

String Representations

InChiKey (Click to copy)

IXAQOQZEOGMIQS-SSQFXEBMSA-N

InChi (Click to copy)

InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1

SMILES (Click to copy)

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