Lipoxin

Lipoxins A4 and B4
Lipoxin A4
Lipoxin B4
Names
Preferred IUPAC name
A4: (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid
B4: (5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyicosa-6,8,10,12-tetraenoic acid
Other names
LXA4 and LXB4
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,12-9+,15-10+/t17-,18+,19-/m1/s1 Y
    Key: UXVRTOKOJOMENI-WLPVFMORSA-N Y
  • A4: 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
    Key: IXAQOQZEOGMIQS-SSQFXEBMSA-N
  • B4: InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,12-9+,15-10+/t17-,18+,19-/m1/s1
    Key: UXVRTOKOJOMENI-WLPVFMORSA-N
  • A4: CCCCC[C@H](O)C=C\C=C/C=CC=CC(O)C(O)CCCC(O)=O
  • B4: O=C(O)CCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCCC
Properties
C20H32O5
Molar mass 352.46508 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

A lipoxin (LX or Lx), an acronym for lipoxygenase interaction product, is a bioactive autacoid metabolite of arachidonic acid made by various cell types. They are categorized as nonclassic eicosanoids and members of the specialized pro-resolving mediator (SPM) family of polyunsaturated fatty acid (PUFA) metabolites. Like other SPMs, LXs form during an inflammatory response and act to resolve it. The first lipoxins identified were lipoxin A4 (LXA4) and lipoxin B4 (LXB4), followed by their respective epimers, the epi-lipoxins 15-epi-LXA4 and 15-epi-LXB4.