Arachidonic_acid_5-hydroperoxide
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)CCCC(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).
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.[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-195543
LY-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: BAYu9773
BAYu9916
CysLTE Tooltip Cysteinyl leukotriene receptor E
Enzyme (inhibitors )
5-LOX Tooltip Arachidonate 5-lipoxygenase
FLAP Tooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103
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
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 .
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