同: 5-hydroperoxyeicosatetraenoic acid

モノヒドロペルオキシ酸
アラキドン酸から5-lipoxygenaseの作用により生じる

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/04 21:25:50」(JST)

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

It is produced by arachidonate 5-lipoxygenase.

Eicosanoid synthesis.

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English Journal

5-lipoxygenase as an endogenous modulator of amyloid β formation in vivo.

Chu J, Praticò D.SourceDepartment of Pharmacology, Temple University, Philadelphia, PA, USA.
Annals of neurology.Ann Neurol.2011 Jan;69(1):34-46. doi: 10.1002/ana.22234. Epub 2010 Nov 17.
OBJECTIVE: The 5-lipoxygenase (5-LO) enzymatic pathway is widely distributed within the central nervous system, and is upregulated in Alzheimer's disease. However, the mechanism whereby it may influence the disease pathogenesis remains elusive.METHODS: We evaluated the molecular mechanism by which 5
PMID 21280074

Dioxygenase activity of epidermal lipoxygenase-3 unveiled: typical and atypical features of its catalytic activity with natural and synthetic polyunsaturated fatty acids.

Zheng Y, Brash AR.SourceDepartment of Pharmacology and the Vanderbilt Institute of Chemical Biology, Vanderbilt University School of Medicine, Nashville, Tennessee 37232, USA.
The Journal of biological chemistry.J Biol Chem.2010 Dec 17;285(51):39866-75. Epub 2010 Oct 4.
Epidermal lipoxygenase-3 (eLOX3) exhibits hydroperoxide isomerase activity implicated in epidermal barrier formation, but its potential dioxygenase activity has remained elusive. We identified herein a synthetic fatty acid, 9E,11Z,14Z-20:3ω6, that was oxygenated by eLOX3 specifically to the 9S-hydr
PMID 20921226

SA14867, a newly synthesized kappa-opioid receptor agonist with antinociceptive and antipruritic effects.

Tsukahara-Ohsumi Y, Tsuji F, Niwa M, Nakamura M, Mizutani K, Inagaki N, Sasano M, Aono H.SourceResearch and Development Center, Santen Pharmaceutical Co., Ltd., Ikoma-shi, Nara, Japan.
European journal of pharmacology.Eur J Pharmacol.2010 Nov 25;647(1-3):62-7. Epub 2010 Sep 4.
SA14867 ((+)-3-Acetyl-6-chloro-2-[2-(3-(N-(2-ethoxyethyl)-N-isopropylamino)propoxy)-5-methoxyphenyl]benzothiazoline O,O'-diacetyl-L-tartrate), a selective kappa-opioid receptor agonist, was synthesized and its antinociceptive and antipruritic effects were investigated. In a functional binding assay,
PMID 20813108

Japanese Journal

Role of Leukotriene B4 in 5-Lipoxygenase Metabolite- and Allergy-Induced Itch-Associated Responses in Mice

Tsuji Fumio,Aono Hiroyuki,Tsuboi Takashi,Murakami Tadahiro,Enomoto Hiroshi,Mizutani Keiko,Inagaki Naoki
Biological & Pharmaceutical Bulletin 33(6), 1050-1053, 2010
… We investigated the role of leukotriene (LT) B4 in 5-lipoxygenase metabolite- and allergy-induced itch-associated responses using SA6541, an LTA4 hydrolase inhibitor. … Itch-associated responses were induced by intradermal injection of 5-hydroperoxyeicosatetraenoic acid (HPETE), a precursor of 5-lipoxygenase metabolites, and passive cutaneous anaphylaxis in ICR mice. …
NAID 130000247978

Detection of 5-Lipoxygenase Activity in the Liverwort Marchantia polyrnorpha L.

KANAMOTO Hirosuke,TAKEMURA Miho,OHYAMA Kanji
Bioscience, biotechnology, and biochemistry 73(11), 2549-2551, 2009-11-23
… We detected 5-LOX (arachidonate 5-lipoxygenase) in the homogenate of Marchantia polymorpha by spectrophotometry and mass spectrometry. … LC/MS/MS analysis indicated that the liverwort 5-LOX produced 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid (5-HPETE) with arachidonic acid as a substrate. … The 5-LOX activity showed a Ca2+ response, as demonstrated for human 5-LOX. …
NAID 10027548337

Related Pictures

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★リンクテーブル★

リンク元	「アラキドン酸」「5-ヒドロペルオキシエイコサテトラエン酸」「5-HETE」
関連記事	「HPETE」

「アラキドン酸」

Arachidonic acid 5-hydroperoxide
Identifiers
CAS Number	74581-83-2
ChemSpider	4446295
IUPHAR/BPS	2483
Jmol interactive 3D	Image
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+ Key: JNUUNUQHXIOFDA-XTDASVJISA-N ; 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).
	verify (what is ?)
	Infobox references

　　[★]

英: arachidonic acid, arachidonate
同: 5,8,11,14-エイコサテトラエン酸 5,8,11,14-eicosatetraenoic acid、5,8,11,14-イコサテトラエン酸 5,8,11,14-icosatetraenoic acid
関: 脂肪酸、必須脂肪酸

炭素数が20で二重結合を4つ有する
CH₃(CH₂)₄(CH=CHCH₂)₄(CH₂)₂COOH
リノール酸から合成される
アラキドン酸は細胞膜の中にホスファチジルイノシトールのC2エステルまたは他のリン脂質のエステルとして蓄えられる (FB.159)

ホスホリパーゼA₂の作用でアラキドン酸として遊離

機能

エイコサノイドの前駆体 (FB.159)

ロイコトリエンやプロスタグランジンの前駆体

prostanoid, leukotriene, epoxideの前駆体

prostanoid： cyclooxygenase pathway

leukotriene：lipoxygenase pathway

epoxide：cytochrome P-450 epoxygenase pathway

代謝

アラキドン酸－(5-lipoxygenase)→5-HPETE
アラキドン酸－(cyclooxygenase)→PGG₂

「5-ヒドロペルオキシエイコサテトラエン酸」

　　[★]

英: 5-hydroperoxyeicosatetraenoic acid, 5-HPETE

「5-HETE」

　　[★]

同: 5-hydroxy-eicosatetraenoic acid
関: 5-HPETE

「HPETE」

　　[★]

同: hydroperoxyeicosatetraenoic acid

関: See Hydroperoxides

モノヒドロペルオキシ酸
5-HPETE
12-HPETE
15-HPETE

関: See Hydroperoxides

匿名

検索

案内

案内

5-HPETE