LXB4   Click here for help

GtoPdb Ligand ID: 5216

Synonyms: lipoxin B4
Immunopharmacology Ligand
Compound class: Metabolite or derivative
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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCCCC(C(C=CC=CC=CC=CC(CCCC(=O)O)O)O)O
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
InChI Key UXVRTOKOJOMENI-WLPVFMORSA-N
References
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]