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Arachidonic acid 5-hydroperoxide

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Arachidonic acid 5-hydroperoxide
Names
Preferred IUPAC name (5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
IUPHAR/BPS
MeSH Arachidonic+acid+5-hydroperoxide
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+Key: JNUUNUQHXIOFDA-XTDASVJISA-N
  • InChI=1/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+Key: JNUUNUQHXIOFDA-XTDASVJIBO
SMILES
  • O=C(O)CCC(OO)/C=C/C=C\C\C=C/C\C=C/CCCCC
Properties
Chemical formula C20H32O4
Molar mass 336.466 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Arachidonic acid 5-hydroperoxide (5-hydroperoxyeicosatetraenoic acid, 5-HPETE) is an intermediate in the metabolism of arachidonic acid by the ALOX5 enzyme in humans or Alox5 enzyme in other mammals. The intermediate is then further metabolized to: a) leukotriene A4 which is then metabolized to the chemotactic factor for leukocytes, leukotriene B4, or to contractors of lung airways, leukotriene C4, leukotriene D4, and leukotriene E4; b) the leukocyte chemotactic factors, 5-hydroxyicosatetraenoic acid and 5-oxo-eicosatetraenoic acid; or c) the specialized pro-resolving mediators of inflammation, lipoxin A4 and lipoxin B4.

Eicosanoid synthesis
Eicosanoids
Precursor
Prostanoids
Prostaglandins (PG)
Precursor
Active
D/J
E/F
I
Thromboxanes (TX)
Leukotrienes (LT)
Precursor
Initial
SRS-A
Eoxins (EX)
Precursor
Eoxins
Nonclassic
By function
Leukotriene signaling modulators
Receptor
(ligands)
BLTTooltip Leukotriene B4 receptor
BLT1Tooltip Leukotriene B4 receptor 1
BLT2Tooltip Leukotriene B4 receptor 2
CysLTTooltip Cysteinyl leukotriene receptor
CysLT1Tooltip Cysteinyl leukotriene receptor 1
CysLT2Tooltip Cysteinyl leukotriene receptor 2
CysLTETooltip Cysteinyl leukotriene receptor E
Enzyme
(inhibitors)
5-LOXTooltip Arachidonate 5-lipoxygenase
12-LOXTooltip Arachidonate 12-lipoxygenase
15-LOXTooltip Arachidonate 15-lipoxygenase
LTA4HTooltip Leukotriene A4 hydrolase
LTB4HTooltip Leukotriene B4 ω-hydroxylase
LTC4STooltip Leukotriene C4 synthase
LTC4HTooltip Leukotriene C4 hydrolase
LTD4Tooltip Leukotriene D4 hydrolase
Others
See also
Receptor/signaling modulators
Prostanoid signaling modulators

References

  1. Haeggström JZ, Funk CD (2011). "Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease". Chemical Reviews. 111 (10): 5866–98. doi:10.1021/cr200246d. PMID 21936577.
  2. Romano M, Cianci E, Simiele F, Recchiuti A (2015). "Lipoxins and aspirin-triggered lipoxins in resolution of inflammation". European Journal of Pharmacology. 760: 49–63. doi:10.1016/j.ejphar.2015.03.083. PMID 25895638.


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