NAV

Leukotriene D4

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Leukotriene D4
DrugBank Accession Number
DB11858
Background

Leukotriene D4 has been used in trials studying the diagnostic of Asthma and Allergic Rhinitis.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 496.66
Monoisotopic: 496.26070819
Chemical Formula
C25H40N2O6S
Synonyms
  • (R-(R*,S*-(E,E,Z,Z)))-N-(S-(1-(4-Carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-L-cysteinyl)glycine
  • 5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid
  • LTD4
  • S-{(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl}-L-cysteinylglycine
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCysteinyl leukotriene receptor 1Not AvailableHumans
UCysteinyl leukotriene receptor 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Leukotrienes
Alternative Parents
Hydroxyeicosatetraenoic acids / Dipeptides / Long-chain fatty acids / N-acyl-alpha amino acids / Alpha amino acid amides / Cysteine and derivatives / Thia fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Dicarboxylic acids and derivatives
show 11 more
Substituents
Alcohol / Aliphatic acyclic compound / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Carbonyl group
show 29 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic sulfide, leukotriene (CHEBI:28666) / Leukotrienes (C05951) / Leukotrienes (LMFA03020006)
Affected organisms
Not Available

Chemical Identifiers

UNII
5FNY4416UE
CAS number
73836-78-9
InChI Key
YEESKJGWJFYOOK-IJHYULJSSA-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
IUPAC Name
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
SMILES
CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0003080
KEGG Compound
C05951
PubChem Compound
5280878
PubChem Substance
347828197
ChemSpider
4444401
BindingDB
50292408
ChEBI
28666
ChEMBL
CHEMBL288943
ZINC
ZINC000004632133
PDBe Ligand
LTD
Wikipedia
Leukotriene_D4
PDB Entries
5ha0

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusNot AvailableAsthma1
Not AvailableCompletedDiagnosticAllergic Rhinitis (AR) / Asthma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00258 mg/mLALOGPS
logP1.17ALOGPS
logP0.76Chemaxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.29Chemaxon
pKa (Strongest Basic)8.05Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area149.95 Å2Chemaxon
Rotatable Bond Count20Chemaxon
Refractivity140.42 m3·mol-1Chemaxon
Polarizability56.08 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002f-8318900000-91190bec2dc8a7c28c8b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zg0-4907400000-3a612131b1b2aeada014
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-3902500000-7389e2c6d92a53acb3ef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fkd-6904100000-9741188fff58c46226b9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-2901100000-c52d4b8f0b816b5089b5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dm-9113100000-dc791ba8d42ae8e6620d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0api-0901000000-561f22b821b529268cb7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-253.0407652
predicted
DarkChem Lite v0.1.0
[M-H]-225.04024
predicted
DeepCCS 1.0 (2019)
[M+H]+252.6136652
predicted
DarkChem Lite v0.1.0
[M+H]+227.4358
predicted
DeepCCS 1.0 (2019)
[M+Na]+253.0992652
predicted
DarkChem Lite v0.1.0
[M+Na]+233.34834
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Cysteinyl leukotriene receptor 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Leukotriene receptor activity
Specific Function
Receptor for cysteinyl leukotrienes mediating bronchoconstriction of individuals with and without asthma. Stimulation by LTD4 results in the contraction and proliferation of smooth muscle, edema, e...
Gene Name
CYSLTR1
Uniprot ID
Q9Y271
Uniprot Name
Cysteinyl leukotriene receptor 1
Molecular Weight
38540.55 Da
References
  1. Lynch KR, O'Neill GP, Liu Q, Im DS, Sawyer N, Metters KM, Coulombe N, Abramovitz M, Figueroa DJ, Zeng Z, Connolly BM, Bai C, Austin CP, Chateauneuf A, Stocco R, Greig GM, Kargman S, Hooks SB, Hosfield E, Williams DL Jr, Ford-Hutchinson AW, Caskey CT, Evans JF: Characterization of the human cysteinyl leukotriene CysLT1 receptor. Nature. 1999 Jun 24;399(6738):789-93. [Article]
  2. Sarau HM, Ames RS, Chambers J, Ellis C, Elshourbagy N, Foley JJ, Schmidt DB, Muccitelli RM, Jenkins O, Murdock PR, Herrity NC, Halsey W, Sathe G, Muir AI, Nuthulaganti P, Dytko GM, Buckley PT, Wilson S, Bergsma DJ, Hay DW: Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor. Mol Pharmacol. 1999 Sep;56(3):657-63. [Article]
  3. Bouchelouche K, Andersen L, Nordling J, Horn T, Bouchelouche P: The cysteinyl-leukotriene D4 induces cytosolic Ca2+ elevation and contraction of the human detrusor muscle. J Urol. 2003 Aug;170(2 Pt 1):638-44. [Article]
Details2. Cysteinyl leukotriene receptor 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Leukotriene receptor activity
Specific Function
Receptor for cysteinyl leukotrienes. The response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system. Stimulation by BAY u9773, a partial agonist, ind...
Gene Name
CYSLTR2
Uniprot ID
Q9NS75
Uniprot Name
Cysteinyl leukotriene receptor 2
Molecular Weight
39634.815 Da
References
  1. Heise CE, O'Dowd BF, Figueroa DJ, Sawyer N, Nguyen T, Im DS, Stocco R, Bellefeuille JN, Abramovitz M, Cheng R, Williams DL Jr, Zeng Z, Liu Q, Ma L, Clements MK, Coulombe N, Liu Y, Austin CP, George SR, O'Neill GP, Metters KM, Lynch KR, Evans JF: Characterization of the human cysteinyl leukotriene 2 receptor. J Biol Chem. 2000 Sep 29;275(39):30531-6. [Article]
  2. Nothacker HP, Wang Z, Zhu Y, Reinscheid RK, Lin SH, Civelli O: Molecular cloning and characterization of a second human cysteinyl leukotriene receptor: discovery of a subtype selective agonist. Mol Pharmacol. 2000 Dec;58(6):1601-8. [Article]

Drug created at October 20, 2016 20:54 / Updated at June 12, 2020 16:53