LTB4   Click here for help

GtoPdb Ligand ID: 2487

Synonyms: leukotriene B4
PDB Ligand Immunopharmacology Ligand
Compound class: Metabolite or derivative
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
Natural/Endogenous Targets
Target
BLT1 receptor
BLT2 receptor
Peroxisome proliferator-activated receptor-α
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
BLT2 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 7.6 pKd - 12
⤷ pKd 7.6 (Kd 2.27x10-8 M) [12]
BLT1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 9.4 pKi -
⤷ pKi 9.4 (Ki 3.8x10-10 M)
BLT2 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 6.8 pEC50 - 9
⤷ pEC50 6.8 (EC50 1.42x10-7 M) [9]
BLT2 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 7.6 pIC50 - 9
⤷ pIC50 7.6 (IC50 2.5x10-8 M) [9]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPV1 Ligand is endogenous in the given species Rn Activator Agonist 4.9 pEC50 - 5
⤷ pEC50 4.9 (EC50 1.25x10-5 M) [5]
Voltage: -60.0 mV
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Peroxisome proliferator-activated receptor-α Ligand is endogenous in the given species ? Agonist Agonist 7.0 pIC50 - 2,6
⤷ pIC50 7.0 [2,6]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at BLT2 receptor 12-hydroxyheptadecatrienoic acid > LTB4 > 12S-HETE = 12S-HPETE > 15S-HETE > 12R-HETE > 20-hydroxy-LTB4 9,11
Potency order of endogenous ligands at BLT1 receptor LTB4 >20-hydroxy-LTB4 >>12R-HETE 11
Targets where the ligand is described in the comment field
Target Comment
CYP4F3 Responsible for ω-hydroxylation of LTB4, LXB4 [8] and polyunsaturated fatty acids [3-4], and ω-hydroxylation of fatty acid epoxides [7]. Possible role in Crohn's disease [1].
CYP4F2 Responsible for ω-hydroxylation of LTB4, LXB4 [8], and tocopherols, including vitamin E [10]. Associated with the warfarin response [13].
Ligand mentioned in the following text fields
1C. Peroxisome proliferator-activated receptors overview
Leukotriene and lipoxin metabolism overview