LXB4   Click here for help

GtoPdb Ligand ID: 5216

Synonyms: lipoxin B4
Immunopharmacology Ligand
Comment: Lipoxin B4 (LXB4) is a member of the lipoxin family. In inflammation it acts as a proresolving mediator [8].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 14
Topological polar surface area 97.99
Molecular weight 352.22
XLogP 3.33
No. Lipinski's rules broken 1
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Isomeric SMILES CCCCC[C@@H]([C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O)O)O
InChI InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,12-9+,15-10+/t17-,18+,19-/m1/s1
1. Corcos L, Lucas D, Le Jossic-Corcos C, Dréano Y, Simon B, Plée-Gautier E, Amet Y, Salaün JP. (2012)
Human cytochrome P450 4F3: structure, functions, and prospects.
Drug Metabol Drug Interact, 27 (2): 63-71. [PMID:22706230]
2. Fer M, Corcos L, Dréano Y, Plée-Gautier E, Salaün JP, Berthou F, Amet Y. (2008)
Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism.
J Lipid Res, 49 (11): 2379-89. [PMID:18577768]
3. Harmon SD, Fang X, Kaduce TL, Hu S, Raj Gopal V, Falck JR, Spector AA. (2006)
Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production.
Prostaglandins Leukot Essent Fatty Acids, 75 (3): 169-77. [PMID:16820285]
4. Karra L, Haworth O, Priluck R, Levy BD, Levi-Schaffer F. (2015)
Lipoxin B₄ promotes the resolution of allergic inflammation in the upper and lower airways of mice.
Mucosal Immunol, 8 (4): 852-62. [PMID:25465102]
5. Kim N, Lannan KL, Thatcher TH, Pollock SJ, Woeller CF, Phipps RP. (2018)
Lipoxin B4 Enhances Human Memory B Cell Antibody Production via Upregulating Cyclooxygenase-2 Expression.
J Immunol, 201 (11): 3343-3351. [PMID:30348736]
6. Le Quéré V, Plée-Gautier E, Potin P, Madec S, Salaün JP. (2004)
Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides.
J Lipid Res, 45 (8): 1446-58. [PMID:15145985]
7. Mizukami Y, Sumimoto H, Isobe R, Minakami S. (1993)
Omega-hydroxylation of lipoxin B4 by human neutrophil microsomes: identification of omega-hydroxy metabolite of lipoxin B4 and catalysis by leukotriene B4 omega-hydroxylase (cytochrome P-450LTB omega).
Biochim Biophys Acta, 1168 (1): 87-93. [PMID:8389204]
8. Parkinson JF. (2006)
Lipoxin and synthetic lipoxin analogs: an overview of anti-inflammatory functions and new concepts in immunomodulation.
Inflamm Allergy Drug Targets, 5 (2): 91-106. [PMID:16613568]
9. Sontag TJ, Parker RS. (2002)
Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status.
J Biol Chem, 277 (28): 25290-6. [PMID:11997390]
10. Zhang JE, Klein K, Jorgensen AL, Francis B, Alfirevic A, Bourgeois S, Deloukas P, Zanger UM, Pirmohamed M. (2017)
Effect of Genetic Variability in the CYP4F2, CYP4F11, and CYP4F12 Genes on Liver mRNA Levels and Warfarin Response.
Front Pharmacol, 8: 323. [PMID:28620303]