LIPID MAPS

Structure Database (LMSD)

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Common Name

Lipoxin A4-d5

Systematic Name

5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic-19,19,20,20,20-d5 acid

Synonyms

LXA4-d5
5S,6R-LipoxinA4-d5
5(S),6(R),15(S)-TriHETE-d5

LM ID

LMFA03040013

Formula

C₂₀H₂₇D₅O₅

Exact Mass

Calculate m/z

357.256359

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Lipoxin A4-d5 (LXA4-d5) is intended for use as an internal standard for the quantification of LXA4 by GC- or LC-MS. 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 (LTB4) 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., Nicolaou, K.C., Webber, S.E., et al. Lipoxin A. Stereochemistry and biosynthesis. The Journal of Biological Chemisty 261(35), 16340-16345 (1986).

2. 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).

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

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

IXAQOQZEOGMIQS-YUMLLTTFSA-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/i1D3,2D2

SMILES (Click to copy)

C(/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O)=C/C=C/[C@@H](O)CCCC([2H])([2H])C([2H])([2H])[2H]