arachidonic acid   Click here for help

GtoPdb Ligand ID: 2391

Synonyms: C20:4
PDB Ligand
Compound class: Metabolite
Comment: Arachidonic acid is a polyunsaturated fatty acid that demonstrates antibacterial activity against Staphylococcus aureus [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 14
Topological polar surface area 37.3
Molecular weight 304.24
XLogP 8.35
No. Lipinski's rules broken 2
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InChI InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ. (2016)
Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions.
Pharmacol Rev, 68 (1): 168-241. [PMID:26721703]
2. Beavers WN, Monteith AJ, Amarnath V, Mernaugh RL, Roberts 2nd LJ, Chazin WJ, Davies SS, Skaar EP. (2019)
Arachidonic Acid Kills Staphylococcus aureus through a Lipid Peroxidation Mechanism.
mBio, 10 (5). [PMID:31575763]
3. Blin S, Chatelain FC, Feliciangeli S, Kang D, Lesage F, Bichet D. (2014)
Tandem pore domain halothane-inhibited K+ channel subunits THIK1 and THIK2 assemble and form active channels.
J Biol Chem, 289 (41): 28202-12. [PMID:25148687]
4. Esperón-Moldes U, Ginarte-Val M, Rodríguez-Pazos L, Fachal L, Martín-Santiago A, Vicente A, Jiménez-Gallo D, Guillén-Navarro E, Sampol LM, González-Enseñat MA et al.. (2020)
Novel CYP4F22 mutations associated with autosomal recessive congenital ichthyosis (ARCI). Study of the CYP4F22 c.1303C>T founder mutation.
PLoS One, 15 (2): e0229025. [PMID:32069299]
5. Feng C, Wang H, Lee M, Zhao J, Lin Z, Yang Y. (2017)
Two missense mutations in CYP4F22 in autosomal recessive congenital ichthyosis.
Clin Exp Dermatol, 42 (1): 98-100. [PMID:27735052]
6. Fink M, Lesage F, Duprat F, Heurteaux C, Reyes R, Fosset M, Lazdunski M. (1998)
A neuronal two P domain K+ channel stimulated by arachidonic acid and polyunsaturated fatty acids.
EMBO J, 17 (12): 3297-308. [PMID:9628867]
7. Hara Y, Wakamori M, Ishii M, Maeno E, Nishida M, Yoshida T, Yamada H, Shimizu S, Mori E, Kudoh J et al.. (2002)
LTRPC2 Ca2+-permeable channel activated by changes in redox status confers susceptibility to cell death.
Mol Cell, 9 (1): 163-73. [PMID:11804595]
8. Kim D, Lewis DL, Graziadei L, Neer EJ, Bar-Sagi D, Clapham DE. (1989)
G-protein beta gamma-subunits activate the cardiac muscarinic K+-channel via phospholipase A2.
Nature, 337 (6207): 557-60. [PMID:2492640]
9. Kim D, Sladek CD, Aguado-Velasco C, Mathiasen JR. (1995)
Arachidonic acid activation of a new family of K+ channels in cultured rat neuronal cells.
J Physiol (Lond.), 484 ( Pt 3): 643-60. [PMID:7623282]
10. Lesage F, Terrenoire C, Romey G, Lazdunski M. (2000)
Human TREK2, a 2P domain mechano-sensitive K+ channel with multiple regulations by polyunsaturated fatty acids, lysophospholipids, and Gs, Gi, and Gq protein-coupled receptors.
J Biol Chem, 275 (37): 28398-405. [PMID:10880510]
11. Liu Y, Liu D, Heath L, Meyers DM, Krafte DS, Wagoner PK, Silvia CP, Yu W, Curran ME. (2001)
Direct activation of an inwardly rectifying potassium channel by arachidonic acid.
Mol Pharmacol, 59 (5): 1061-8. [PMID:11306688]
12. Maingret F, Patel AJ, Lazdunski M, Honoré E. (2001)
The endocannabinoid anandamide is a direct and selective blocker of the background K(+) channel TASK-1.
EMBO J, 20 (1-2): 47-54. [PMID:11226154]
13. Müller G, Ayoub M, Storz P, Rennecke J, Fabbro D, Pfizenmaier K. (1995)
PKC zeta is a molecular switch in signal transduction of TNF-alpha, bifunctionally regulated by ceramide and arachidonic acid.
EMBO J, 14 (9): 1961-9. [PMID:7744003]
14. Nilsson T, Ivanov IV, Oliw EH. (2010)
LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22.
Arch Biochem Biophys, 494 (1): 64-71. [PMID:19919823]
15. Nohara T, Ohno Y, Kihara A. (2021)
Impaired production of the skin barrier lipid acylceramide by CYP4F22 ichthyosis mutations.
J Dermatol Sci, 101 (1): 69-71. [PMID:33067036]
16. Ohno Y, Nakamichi S, Ohkuni A, Kamiyama N, Naoe A, Tsujimura H, Yokose U, Sugiura K, Ishikawa J, Akiyama M et al.. (2015)
Essential role of the cytochrome P450 CYP4F22 in the production of acylceramide, the key lipid for skin permeability barrier formation.
Proc Natl Acad Sci U S A, 112 (25): 7707-12. [PMID:26056268]
17. Patel AJ, Honoré E, Maingret F, Lesage F, Fink M, Duprat F, Lazdunski M. (1998)
A mammalian two pore domain mechano-gated S-like K+ channel.
EMBO J, 17 (15): 4283-90. [PMID:9687497]
18. Richieri GV, Ogata RT, Kleinfeld AM. (1994)
Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB.
J Biol Chem, 269 (39): 23918-30. [PMID:7929039]
19. Richieri GV, Ogata RT, Zimmerman AW, Veerkamp JH, Kleinfeld AM. (2000)
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
Biochemistry, 39 (24): 7197-204. [PMID:10852718]
20. Sano Y, Inamura K, Miyake A, Mochizuki S, Kitada C, Yokoi H, Nozawa K, Okada H, Matsushime H, Furuichi K. (2003)
A novel two-pore domain K+ channel, TRESK, is localized in the spinal cord.
J Biol Chem, 278 (30): 27406-12. [PMID:12754259]
21. Schaffer JE, Lodish HF. (1994)
Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein.
Cell, 79 (3): 427-36. [PMID:7954810]
22. Solanki M, Pointon A, Jones B, Herbert K. (2018)
Cytochrome P450 2J2: Potential Role in Drug Metabolism and Cardiotoxicity.
Drug Metab Dispos, 46 (8): 1053-1065. [PMID:29695613]
23. Stahl A, Hirsch DJ, Gimeno RE, Punreddy S, Ge P, Watson N, Patel S, Kotler M, Raimondi A, Tartaglia LA et al.. (1999)
Identification of the major intestinal fatty acid transport protein.
Mol Cell, 4 (3): 299-308. [PMID:10518211]
24. Villarroel A, Schwarz TL. (1996)
Inhibition of the Kv4 (Shal) family of transient K+ currents by arachidonic acid.
J Neurosci, 16 (8): 2522-32. [PMID:8786428]
25. Wang H, Shi H, Wang Z. (1999)
Nicotine depresses the functions of multiple cardiac potassium channels.
Life Sci, 65 (12): PL143-9. [PMID:10503950]
26. Watanabe H, Vriens J, Prenen J, Droogmans G, Voets T, Nilius B. (2003)
Anandamide and arachidonic acid use epoxyeicosatrienoic acids to activate TRPV4 channels.
Nature, 424 (6947): 434-8. [PMID:12879072]
27. Wu S, Moomaw CR, Tomer KB, Falck JR, Zeldin DC. (1996)
Molecular cloning and expression of CYP2J2, a human cytochrome P450 arachidonic acid epoxygenase highly expressed in heart.
J Biol Chem, 271 (7): 3460-8. [PMID:8631948]
28. Wu Z, Lee D, Joo J, Shin JH, Kang W, Oh S, Lee DY, Lee SJ, Yea SS, Lee HS et al.. (2013)
CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems.
Antimicrob Agents Chemother, 57 (11): 5448-56. [PMID:23959307]
29. Zeldin DC, DuBois RN, Falck JR, Capdevila JH. (1995)
Molecular cloning, expression and characterization of an endogenous human cytochrome P450 arachidonic acid epoxygenase isoform.
Arch Biochem Biophys, 322 (1): 76-86. [PMID:7574697]