LIPID MAPS

Structure Database (LMSD)

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Common Name

epi-Lipoxin A4

Systematic Name

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

Synonyms

5S,6S-Lipoxin A4 epi-LXA4

LM ID

LMFA03040003

Formula

C₂₀H₃₂O₅

Exact Mass

Calculate m/z

352.224975

Sum Composition

FA 20:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

6(S)-Lipoxin A4 (6(S)-LXA4) is an isomer of the trihydroxy fatty acid LXA4 . It is formed from arachidonic acid through double lipoxygenase-catalyzed reactions initiated by either 5-lipoxygenase (5-LO) followed by 12- or 15-LO, with a leukotriene A4 (LTA4) intermediate, or by 15-LO followed by 5-LO, with 15(S)-HETE and 5(S)-Hp-15(S)-HETE intermediates.¹ The generation of 6(S)-LXA4 and LXA4 typically requires transcellular metabolism of arachidonic acid.^1,2 For example, LTA4 synthesized in neutrophils by 5-LO is metabolized to LXA4 in platelets by 12-LO.¹ 6(S)-LXA4 has been detected in co-incubations of human polymorphonuclear leukocytes (PMNs) and platelets.³

This information has been provided by Cayman Chemical

References

1. Serhan, C.N., Chiang, N., and Van Dyke, T.E. Resolving inflammation: Dual anti-inflammatory and pro-resolution lipid mediators. Nat. Rev. Immunol. 8(5), 349-361 (2008).

2. Serhan, C.N., and Sheppard, K.-A. Lipoxin formation during human neutrophil-platelet interactions. Evidence for the transformation of leukotriene A4 by platelet 12-lipoxygenase in vitro. J. Clin. Invest. 85(3), 772-780 (1990).

3. Homann, J., Lehmann, C., Kahnt, A.S., et al. Chiral chromatography-tandem mass spectrometry applied to the determination of pro-resolving lipid mediators. J. Chromatogr. A 1360, 150-163 (2014).

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)

IXAQOQZEOGMIQS-UZDWIPAXSA-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