5S-HETE   Click here for help

GtoPdb Ligand ID: 3390

Synonyms: 5-(S)-hydroxyeicosatetraenoic acid
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 57.53
Molecular weight 320.24
XLogP 6.62
No. Lipinski's rules broken 2
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InChI InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
1. Grant GE, Rokach J, Powell WS. (2009)
5-Oxo-ETE and the OXE receptor.
Prostaglandins Other Lipid Mediat, 89 (3-4): 98-104. [PMID:19450703]
2. Hosoi T, Koguchi Y, Sugikawa E, Chikada A, Ogawa K, Tsuda N, Suto N, Tsunoda S, Taniguchi T, Ohnuki T. (2002)
Identification of a novel human eicosanoid receptor coupled to G(i/o).
J Biol Chem, 277 (35): 31459-65. [PMID:12065583]
3. Hosoi T, Sugikawa E, Chikada A, Koguchi Y, Ohnuki T. (2005)
TG1019/OXE, a Galpha(i/o)-protein-coupled receptor, mediates 5-oxo-eicosatetraenoic acid-induced chemotaxis.
Biochem Biophys Res Commun, 334 (4): 987-95. [PMID:16039985]
4. Jones CE, Holden S, Tenaillon L, Bhatia U, Seuwen K, Tranter P, Turner J, Kettle R, Bouhelal R, Charlton S, Nirmala NR, Jarai G, Finan P. (2003)
Expression and characterization of a 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid receptor highly expressed on human eosinophils and neutrophils.
Mol Pharmacol, 63: 471-477. [PMID:12606753]
5. O'Flaherty JT, Cordes JF, Lee SL, Samuel M, Thomas MJ. (1994)
Chemical and biological characterization of oxo-eicosatetraenoic acids.
Biochim Biophys Acta, 1201 (3): 505-15. [PMID:7803484]
6. O'Flaherty JT, Taylor JS, Thomas MJ. (1998)
Receptors for the 5-oxo class of eicosanoids in neutrophils.
J Biol Chem, 273 (49): 32535-41. [PMID:9829988]
7. Patel P, Cossette C, Anumolu JR, Gravel S, Lesimple A, Mamer OA, Rokach J, Powell WS. (2008)
Structural requirements for activation of the 5-oxo-6E,8Z, 11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) receptor: identification of a mead acid metabolite with potent agonist activity.
J Pharmacol Exp Ther, 325 (2): 698-707. [PMID:18292294]
8. Powell WS, Gravel S, MacLeod RJ, Mills E, Hashefi M. (1993)
Stimulation of human neutrophils by 5-oxo-6,8,11,14-eicosatetraenoic acid by a mechanism independent of the leukotriene B4 receptor.
J Biol Chem, 268 (13): 9280-6. [PMID:8387490]
9. Powell WS, Gravelle F, Gravel S. (1992)
Metabolism of 5(S)-hydroxy-6,8,11,14-eicosatetraenoic acid and other 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human polymorphonuclear leukocytes.
J Biol Chem, 267 (27): 19233-41. [PMID:1326548]
10. Schwenk U, Schröder JM. (1995)
5-Oxo-eicosanoids are potent eosinophil chemotactic factors. Functional characterization and structural requirements.
J Biol Chem, 270 (25): 15029-36. [PMID:7797484]