Arachidonic acid 5-hydroperoxide

Arachidonic acid 5-hydroperoxide
Identifiers

CAS Number	74581-83-2^Y
3D model (Jmol)	Interactive image
ChemSpider	4446295^Y
IUPHAR/BPS	2483
MeSH	Arachidonic+acid+5-hydroperoxide
PubChem	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+^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
SMILES O=C(O)CCCC(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).
Y verify (what is ^YN ?)
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.

Precursor

Precursor

Active

D/J	D₂

E/F	E₂ (Dinoprostone) E₁ (Alprostadil) F_2α (Dinoprost):

I	I₂ (Prostacyclin/Epoprostenol):

Precursor	Arachidonic acid 5-hydroperoxide

Initial	A₄ B₄

SRS-A	C₄ D₄ E₄

Precursor	Arachidonic acid 15-hydroperoxide

Eoxins	A₄ C₄ D₄ E₄

By function

BLT₁	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

BLT₂	Agonists: 12-HETE 12-HHT 12-HpETE 15-HETE 15-HpETE 20-Hydroxy-LTB₄ Leukotriene B₄ Antagonists: CP-195543 LY-255283 ZK-158252

CysLT₁	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

CysLT₂	Agonists: Leukotriene C₄ Leukotriene D₄ Leukotriene E₄ Antagonists: BAYu9773 BAYu9916

CysLT_E	Agonists: Leukotriene E₄

5-Lipoxygenase	2-TEDC Baicalein BW-A4C BW-B70C Caffeic acid CDC CJ-13610 Curcumin Fenleuton Hyperforin Hypericum perforatum (St. John's Wort) Meclofenamic acid (meclofenamate) Minocycline N-Stearoyldopamine Timegadine Zileuton FLAP inhibitors: AM-103 AM-679 BAYx1005 MK-591 MK-886

12-Lipoxygenase	2-TEDC 3-Methoxytropolone Baicalein CDC

15-Lipoxygenase	2-TEDC CDC Luteolin PD-146176

LTA₄ hydrolase	Acebilustat Captopril DG-051 Fosinoprilat JNJ-26993135 SA-6541 SC-57461A Ubenimex (bestatin)

LTB₄ ω-hydroxylase	17-Octadecynoic acid

LTC₄ synthase	Azelastine MK-886

LTC₄ hydrolase	Acivicin Serine-borate complex

LTD₄ hydrolase	Cilastatin Ubenimex (bestatin)

Others

See also: Prostanoids

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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