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
CAS Number
  • 74581-83-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4446295 checkY
IUPHAR/BPS
  • 2483
MeSH Arachidonic+acid+5-hydroperoxide
PubChem CID
  • 5280778
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+ checkY
    Key: JNUUNUQHXIOFDA-XTDASVJISA-N checkY
  • 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
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
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.[1][2]

Eicosanoid synthesis
  • v
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PrecursorProstanoids
Prostaglandins (PG)
Precursor
  • H2
Active
D/J
  • D2
E/F
  • E2 (Dinoprostone)
  • E1 (Alprostadil)
  • F (Dinoprost):
I
  • I2 (Prostacyclin/Epoprostenol):
Thromboxanes (TX)
  • A2
  • B2
Leukotrienes (LT)
Precursor
  • Arachidonic acid 5-hydroperoxide
Initial
  • A4
  • B4
SRS-A
  • C4
  • D4
  • E4
Eoxins (EX)
Precursor
  • Arachidonic acid 15-hydroperoxide
Eoxins
  • A4
  • C4
  • D4
  • E4
Nonclassic
By function
  • labor stimulation:
    • PGE2 (Dinoprostone)
    • PGF (Dinoprost)
  • v
  • t
  • e
Receptor
(ligands)
BLTTooltip Leukotriene B4 receptor
BLT1Tooltip Leukotriene B4 receptor 1
  • Agonists: 12-HETE
  • 20-Hydroxy-LTB4
  • Leukotriene B4
  • LY-255283
  • 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
BLT2Tooltip Leukotriene B4 receptor 2
  • Antagonists: CP-195543
  • LY-255283
  • ZK-158252
CysLTTooltip Cysteinyl leukotriene receptor
CysLT1Tooltip Cysteinyl leukotriene receptor 1
  • Agonists: Leukotriene C4
  • Leukotriene D4
  • Leukotriene E4
  • 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
CysLT2Tooltip Cysteinyl leukotriene receptor 2
  • Agonists: Leukotriene C4
  • Leukotriene D4
  • Leukotriene E4
  • Antagonists: BAYu9773
  • BAYu9916
CysLTETooltip Cysteinyl leukotriene receptor E
  • Agonists: Leukotriene E4
Enzyme
(inhibitors)
5-LOXTooltip Arachidonate 5-lipoxygenase
  • FLAPTooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103
  • AM-679
  • BAYx1005
  • MK-591
  • MK-886
12-LOXTooltip Arachidonate 12-lipoxygenase
15-LOXTooltip Arachidonate 15-lipoxygenase
LTA4HTooltip Leukotriene A4 hydrolase
LTB4HTooltip Leukotriene B4 ω-hydroxylase
  • 17-Octadecynoic acid
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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