Arachidonic acid 5-hydroperoxide Names Preferred IUPAC name (5S ,6E ,8Z ,11Z ,14Z )-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid
Identifiers ChemSpider MeSH Arachidonic+acid+5-hydroperoxide 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+
Y Key: JNUUNUQHXIOFDA-XTDASVJISA-N
Y 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
O=C(O)CCC[C@H](OO)/C=C/C=C\C\C=C/C\C=C/CCCCC
Properties C20 H32 O4 Molar mass 336.466 g/mol Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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.[ 1] [ 2]
Eicosanoid synthesis
Receptor (ligands )
BLT Tooltip Leukotriene B4 receptor
BLT1 Tooltip Leukotriene B4 receptor 1 Antagonists: 20-Carboxy-LTB4 Amelubant CGS-23131 (LY-223982) CGS-25019C CP-105696 CP-195543 Etalocib LY-293111 Moxilubant ONO-4057 RG-14893 RP-69698 SB-209247 SC-53228 Ticolubant U-75302 ZK-158252 BLT2 Tooltip Leukotriene B4 receptor 2 Antagonists: CP-195543LY-255283 ZK-158252
CysLT Tooltip Cysteinyl leukotriene receptor
CysLT1 Tooltip Cysteinyl leukotriene receptor 1 Antagonists: Ablukast BAYu9773 BAYu9916 BAYx7195 Cinalukast FPL-55712 ICI-198615 Iralukast LY-170680 Masilukast MK-571 Montelukast ONO-1078 Pobilukast Pranlukast Ritolukast SKF-104353 SR-2640 Sulukast Tipelukast Tomelukast Verlukast Zafirlukast ZD-3523 CysLT2 Tooltip Cysteinyl leukotriene receptor 2 Antagonists: BAYu9773BAYu9916 CysLTE Tooltip Cysteinyl leukotriene receptor E
Enzyme (inhibitors )
5-LOX Tooltip Arachidonate 5-lipoxygenase FLAP Tooltip Arachidonate 5-lipoxygenase-activating protein inhibitors:AM-679 BAYx1005 MK-591 MK-886 12-LOX Tooltip Arachidonate 12-lipoxygenase 15-LOX Tooltip Arachidonate 15-lipoxygenase LTA4 H Tooltip Leukotriene A4 hydrolase LTB4 H Tooltip Leukotriene B4 ω-hydroxylase LTC4 S Tooltip Leukotriene C4 synthase LTC4 H Tooltip Leukotriene C4 hydrolase LTD4 Tooltip Leukotriene D4 hydrolase
Others See also Receptor/signaling modulators Prostanoid signaling modulators
References ^ 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 . ^ 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 .
