Arachidonic acid 5-hydroperoxide
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| Names
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Preferred IUPAC name
(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid |
| Identifiers
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| ChemSpider
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| MeSH
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Arachidonic+acid+5-hydroperoxide
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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
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O=C(O)CCC[C@H](OO)/C=C/C=C\C\C=C/C\C=C/CCCCC
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| Properties
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C20H32O4
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| Molar mass
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336.466 g/mol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references
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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.[1][2]
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Receptor
(ligands) | | BLTTooltip Leukotriene B4 receptor | | BLT1Tooltip Leukotriene B4 receptor 1 |
- 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
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| BLT2Tooltip Leukotriene B4 receptor 2 |
- Antagonists: CP-195543
- LY-255283
- ZK-158252
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| CysLTTooltip Cysteinyl leukotriene receptor | | CysLT1Tooltip Cysteinyl leukotriene receptor 1 |
- 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
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| CysLT2Tooltip Cysteinyl leukotriene receptor 2 |
- Antagonists: BAYu9773
- BAYu9916
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| CysLTETooltip Cysteinyl leukotriene receptor E | |
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Enzyme
(inhibitors) | | 5-LOXTooltip Arachidonate 5-lipoxygenase |
- FLAPTooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103
- AM-679
- BAYx1005
- MK-591
- MK-886
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| 12-LOXTooltip Arachidonate 12-lipoxygenase | |
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| 15-LOXTooltip Arachidonate 15-lipoxygenase | |
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| LTA4HTooltip Leukotriene A4 hydrolase | |
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| LTB4HTooltip Leukotriene B4 ω-hydroxylase | |
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| LTC4STooltip Leukotriene C4 synthase | |
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| LTC4HTooltip Leukotriene C4 hydrolase | |
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| LTD4Tooltip Leukotriene D4 hydrolase | |
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| Others | |
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- See also
- Receptor/signaling modulators
- Prostanoid signaling modulators
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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.