LTB4   Click here for help

GtoPdb Ligand ID: 2487

Synonyms: leukotriene B4
PDB Ligand Immunopharmacology Ligand
Comment: Leukotriene LTD4 is a BLT1/BLT2 receptor agonist. It induces contraction of smooth muscle, resulting in bronchoconstriction and vasoconstriction. and functions as a potent chemotactic factor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 77.76
Molecular weight 336.23
XLogP 4.5
No. Lipinski's rules broken 1
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InChI InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,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. Devchand PR, Keller H, Peters JM, Vazquez M, Gonzalez FJ, Wahli W. (1996)
The PPARalpha-leukotriene B4 pathway to inflammation control.
Nature, 384 (6604): 39-43. [PMID:8900274]
3. 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]
4. 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]
5. Hwang SW, Cho H, Kwak J, Lee SY, Kang CJ, Jung J, Cho S, Min KH, Suh YG, Kim D et al.. (2000)
Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances.
Proc Natl Acad Sci USA, 97 (11): 6155-60. [PMID:10823958]
6. Krey G, Braissant O, L'Horset F, Kalkhoven E, Perroud M, Parker MG, Wahli W. (1997)
Fatty acids, eicosanoids, and hypolipidemic agents identified as ligands of peroxisome proliferator-activated receptors by coactivator-dependent receptor ligand assay.
Mol Endocrinol, 11 (6): 779-91. [PMID:9171241]
7. 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]
8. 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]
9. Okuno T, Iizuka Y, Okazaki H, Yokomizo T, Taguchi R, Shimizu T. (2008)
12(S)-Hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2.
J Exp Med, 205 (4): 759-66. [PMID:18378794]
10. 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]
11. Yokomizo T, Kato K, Hagiya H, Izumi T, Shimizu T. (2001)
Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2.
J Biol Chem, 276 (15): 12454-9. [PMID:11278893]
12. Yokomizo T, Kato K, Terawaki K, Izumi T, Shimizu T. (2000)
A second leukotriene B(4) receptor, BLT2. A new therapeutic target in inflammation and immunological disorders.
J Exp Med, 192 (3): 421-32. [PMID:10934230]
13. 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]