LTB4   Click here for help

GtoPdb Ligand ID: 2487

Synonyms: leukotriene B4
PDB Ligand Immunopharmacology Ligand
Compound class: Metabolite
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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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 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
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=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
Isomeric SMILES CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O
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
InChI Key VNYSSYRCGWBHLG-AMOLWHMGSA-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. 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]