:Arachidonic acid 5-hydroperoxide

{{chembox

| verifiedrevid = 452418850

| ImageFile=5-Hydroperoxyeicosatetraenoic acid.svg

| ImageSize=

| PIN=(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid

| OtherNames=

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 2483

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=74581-83-2

| PubChem=5280778

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4446295

| SMILES = O=C(O)CCC[C@H](OO)/C=C/C=C\C\C=C/C\C=C/CCCCC

| 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+

| InChIKey = JNUUNUQHXIOFDA-XTDASVJIBO

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JNUUNUQHXIOFDA-XTDASVJISA-N

| MeSHName=Arachidonic+acid+5-hydroperoxide

}}

|Section2={{Chembox Properties

| Formula=C₂₀H₃₂O₄

| MolarMass=336.466 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

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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.{{cite journal | vauthors = Haeggström JZ, Funk CD | title = Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease | journal = Chemical Reviews | volume = 111 | issue = 10 | pages = 5866–98 | year = 2011 | pmid = 21936577 | doi = 10.1021/cr200246d }}{{cite journal | vauthors = Romano M, Cianci E, Simiele F, Recchiuti A | title = Lipoxins and aspirin-triggered lipoxins in resolution of inflammation | journal = European Journal of Pharmacology | volume = 760 | pages = 49–63 | year = 2015 | pmid = 25895638 | doi = 10.1016/j.ejphar.2015.03.083 }}

Image:Eicosanoid synthesis.svg

{{Eicosanoids}}

{{Leukotrienergics}}