Arachidonic acid 5-hydroperoxide

Arachidonic acid 5-hydroperoxide

Identifiers
CAS number	74581-83-2
PubChem	5280778
ChemSpider	4446295^Y
MeSH	Arachidonic+acid+5-hydroperoxide
Jmol-3D images	Image 1
SMILES O=C(O)CCCC(OO)/C=C/C=C\C\C=C/C\C=C/CCCCC
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
Properties
Molecular formula	C₂₀H₃₂O₄
Molar mass	336.466 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Arachidonic acid 5-hydroperoxide (5-hydroperoxyeicosatetraenoic acid, 5-HPETE) is an intermediate in the production of leukotriene A4 from arachidonic acid.

It is produced by arachidonate 5-lipoxygenase.

Autacoids, unsaturated fatty acids: Eicosanoids

Precursor

Arachidonic acid

Prostanoids

Prostaglandins (PG) and
analogues

Precursor

H₂

Active

D/J	D₂

E/F	E₂ (Dinoprostone): Enprostil · Sulprostone E₁ (Alprostadil): Misoprostol · Gemeprost F_2α (Dinoprost): Bimatoprost · Carboprost · Latanoprost · Tafluprost · Travoprost · Unoprostone

I	I₂ (Prostacyclin/Epoprostenol): Beraprost · Iloprost · Treprostinil

Thromboxanes (TX)

A₂ · B₂

Leukotrienes (LT)

Precursor	Arachidonic acid 5-hydroperoxide

Initial	A₄ · B₄

SRS-A	C₄ · D₄ · E₄

Nonclassic

Lipoxins (A₄, B₄) · Virodhamine

By function

bronchoconstriction (PGF_2α, TXA₂, LTC₄, LTD₄, LTE₄)

vasoconstriction (PGF_2α, TXA₂, TXB₂) · vasodilation (PGE₂, PGI₂, LTC₄, LTD₄, LTE₄)

platelets: induce (TXA₂) inhibit (PGD₂, PGI₂) · leukocytes: induce (TXA₂, LTB₄) inhibit (PGD₂, PGE₂)

fever stimulation: (PGE₂)

labor stimulation: (PGE₂ (Dinoprostone), PGF_2α (Dinoprost))

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i