LIPID MAPS

Structure Database (LMSD)

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Common Name

Lipoxin A5

Systematic Name

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

Synonyms

LXA5

LM ID

LMFA03040012

Formula

C₂₀H₃₀O₅

Exact Mass

Calculate m/z

350.209326

Sum Composition

FA 20:5;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Biological Context

Lipoxin A5 (LXA5) is produced by enzymatic transformation of EPA by leukocytes.¹ LXA5 slowly contracts pulmonary parenchymal strips from guinea pig with similar potency to that of LXA4 and LXB4.2 However, LXA5 does not exert the vasodilatory effects on aortic smooth muscle exhibited by LXA4 and LXB4.2

This information has been provided by Cayman Chemical

References

1. Wong, P.Y.K., Hughes, R., and Lam, B. Lipoxene: A new group of trihydroxy pentaenes of eicosapentaenoic acid derived from porcine leukocytes. Biochem. Biophys. Res. Commun. 126(2), 763-772 (1985).

2. Stahl, G.L., Tsao, P., Lefer, A.M., et al. Pharmacologic profile of lipoxins A5 and B5: new biologically active eicosanoids. Eur. J. Pharmacol. 163, 55-60 (1989).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipoxins of the 5-series derived from eicosapentaenoic acid.,
Adv Exp Med Biol, 1988

Pubmed ID: 2844069

String Representations

InChiKey (Click to copy)

ZZMKOZNTEJVKRY-YJUORNCYSA-N

InChi (Click to copy)

InChI=1S/C20H30O5/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/h3-10,13-14,17-19,21-23H,2,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,8-3-,13-9+,14-10+/t17-,18+,19-/m0/s1

SMILES (Click to copy)

C(CCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)C/C=C\CC)(=O)O