LTD4   Click here for help

GtoPdb Ligand ID: 3353

Synonyms: leukotriene D4
Compound class: Metabolite or derivative
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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
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 8
Hydrogen bond donors 5
Rotatable bonds 21
Topological polar surface area 175.25
Molecular weight 496.26
XLogP 2.23
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=CC=CC=CC(C(CCCC(=O)O)O)SCC(C(=O)NCC(=O)O)N
Isomeric SMILES CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SCC(C(=O)NCC(=O)O)N
InChI InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20?,21-,22+/m0/s1
InChI Key YEESKJGWJFYOOK-LDDGIIIKSA-N
Natural/Endogenous Targets
Target
CysLT1 receptor
CysLT2 receptor
GPR17
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
γ-Glutamyltransferase 2.3.2.2 LTC4 + H2O => LTD4 + L-glutamate
Dipeptidase 1 3.4.13.19 LTD4 + H2O = LTE4 + glycine
Dipeptidase 2 3.4.13.19 LTD4 + H2O = LTE4 + glycine
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CysLT2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.3 – 8.1 pKi - 3
⤷ pKi 7.3 – 8.1 Ki1 and Ki2 against [3H]LTC4 in human lung parenchyma [3]
GPR17 Ligand is endogenous in the given species Mm Agonist Agonist 9.2 pEC50 - 12
⤷ pEC50 9.2 (EC50 6.3x10-10 M) [12]
CysLT1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.3 – 9.4 pEC50 - 2,4,13,15-16,18-19
⤷ pEC50 9.4 (EC50 4x10-10 M) pigment dispersion in X. laevis melanophores [13]
pEC50 8.5 (EC50 3x10-9 M) Ca2+ activated chloride conductance in X. laevis oocytes [13]
pEC50 8.5 (EC50 3.4x10-9 M) Ca2+ mobilisation assay in U937 cells [2]
pEC50 7.3 – 9.2 (EC50 4.6x10-8 – 6x10-10 M) Ca2+ mobilisation assay in COS-7 or HEK-293 cells [4,13,15-16,18-19]
GPR17 Ligand is endogenous in the given species Hs Agonist Agonist 8.1 – 8.4 pEC50 - 5
⤷ pEC50 8.1 – 8.4 (EC50 7.2x10-9 – 4.4x10-9 M) [5]
Description: [35S]GTPγS binding to COS-7 cell membranes expressing hGPR17.
CysLT2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.8 – 8.6 pEC50 - 4,11,15,18,20
⤷ pEC50 8.0 – 8.6 (EC50 9.3x10-9 – 2.5x10-9 M) Ca2+ mobolisation assay in HEK-293 cells [4,15,18]
pEC50 7.5 (EC50 3.5x10-8 M) β-arrestin assay in C2C12 [20]
pEC50 7.4 (EC50 3.6x10-8 M) Ca2+ mobilization assay in HUVEC [4]
pEC50 6.8 – 7.0 (EC50 1.44x10-7 – 1.04x10-7 M) aequorin-based Ca2+ assay in HEK-293 cells [11,20]
CysLT1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 8.1 pIC50 - 16
⤷ pIC50 8.1 (IC50 9x10-9 M) against [3H]LTD4 in HEK-293 cells [16]
CysLT2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.2 – 8.1 pIC50 - 15,18
⤷ pIC50 8.1 (IC50 7x10-9 M) against [3H]LTD4 in HEK-293 cells [15]
pIC50 7.2 (IC50 5.9x10-8 M) against [3H]LTC4 in COS-1 cells [18]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at CysLT1 receptor LTD4 > LTC4 > LTE4 13,16
Potency order of endogenous ligands at CysLT2 receptor LTC4 ≥ LTD4 >> LTE4 11,15,18
Potency order of endogenous and other ligands at FPR2/ALX LXA4 = aspirin triggered lipoxin A4 = ATLa2 = resolvin D1 > LTC4 = LTD4 >> 15-deoxy-LXA4 >> fMet-Leu-Phe 6,8-10,17
Targets where the ligand is described in the comment field
Target Comment
GPR17 Reported to be a dual leukotriene and UDP receptor [5]. Another group instead proposed that GPR17 functions as a negative regulator of the CysLT1 receptor response to leukotriene D4 (LTD4). For further discussion, see [7]. Reported to antagonize CysLT1 receptor signalling in vivo and in vitro [14]. See reviews [1] and [7].
Ligand mentioned in the following text fields
Leukotriene and lipoxin metabolism overview
Leukotriene receptors overview
Leukotriene and lipoxin metabolism comments