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

Identification

Name
Leukotriene B4
Accession Number
DB12961
Type
Small Molecule
Groups
Investigational
Description

Leukotriene B4 has been used in trials studying the treatment of HIV Infections.

Structure
Thumb
Synonyms
  • LTB4
Categories
UNII
1HGW4DR56D
CAS number
71160-24-2
Weight
Average: 336.4657
Monoisotopic: 336.230059512
Chemical Formula
C20H32O4
InChI Key
VNYSSYRCGWBHLG-AMOLWHMGSA-N
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
IUPAC Name
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
SMILES
CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULeukotriene B4 receptor 1Not AvailableHuman
ULeukotriene B4 receptor 2Not AvailableHuman
UPeroxisome proliferator-activated receptor alpha
activator
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001085
KEGG Compound
C02165
PubChem Compound
5280492
PubChem Substance
347829101
ChemSpider
4444132
BindingDB
50013889
ChEBI
15647
ChEMBL
CHEMBL65061
HET
LTB
Wikipedia
Leukotriene_B4
PDB Entries
3zuo

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedDiagnosticSkin Inflammation1

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 Solubility0.0152 mg/mLALOGPS
logP5.46ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m3·mol-1ChemAxon
Polarizability39.51 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gb9-0019000000-39d0f0947681f1f7fc37
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0v4i-5498000000-4599d3006831091f926c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9450000000-b6647dcbb40f3175983d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0029000000-d2d2e17f68f90518361e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014r-2269000000-1a60fcc2f712b3beea2a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9340000000-edfb4e3fd8a8f4667ead
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-000i-0419000000-061132d646cd5dd85a1b
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00ks-0829000000-7da7ab59ee0d4812767b
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0002-0933000000-3fb381ce0f3609a90222
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0udj-0931000000-ccfdaa3226146fe9edc3
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0udj-1940000000-ef988be204f5c54f4b21
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0r00-1910000000-e16cc958487f06dc4287
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0006-6900000000-a356f0334bf220eb54cc
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-052f-9700000000-66a6a217eba63b4874d1
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0a4l-7900000000-aeb350579ea4a84117d0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-0619000000-dc49d3f4ab097db18f18

Taxonomy

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 / Long-chain fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Leukotriene / Hydroxyeicosatetraenoic acid / Long-chain fatty acid / Hydroxy fatty acid / Fatty acid / Unsaturated fatty acid / Secondary alcohol / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
long-chain fatty acid, leukotriene, dihydroxy monocarboxylic acid, polyunsaturated fatty acid, hydroxy fatty acid (CHEBI:15647) / Leukotrienes (C02165) / Leukotrienes (LMFA03020001)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Receptor for extracellular ATP > UTP and ADP. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. May be the cardiac P2Y r...
Gene Name
LTB4R
Uniprot ID
Q15722
Uniprot Name
Leukotriene B4 receptor 1
Molecular Weight
37556.925 Da
References
  1. Wang S, Gustafson E, Pang L, Qiao X, Behan J, Maguire M, Bayne M, Laz T: A novel hepatointestinal leukotriene B4 receptor. Cloning and functional characterization. J Biol Chem. 2000 Dec 29;275(52):40686-94. [PubMed:11006272]
  2. Sawyer JS, Bach NJ, Baker SR, Baldwin RF, Borromeo PS, Cockerham SL, Fleisch JH, Floreancig P, Froelich LL, Jackson WT, et al.: Synthetic and structure/activity studies on acid-substituted 2-arylphenols: discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5- hydroxyphenoxy]-propoxy]phenoxy]benzoic acid, a high-affinity leukotriene B4 receptor antagonist. J Med Chem. 1995 Oct 27;38(22):4411-32. [PubMed:7473568]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Leukotriene receptor activity
Specific Function
Low-affinity receptor for leukotrienes including leukotriene B4. Mediates chemotaxis of granulocytes and macrophages. The response is mediated via G-proteins that activate a phosphatidylinositol-ca...
Gene Name
LTB4R2
Uniprot ID
Q9NPC1
Uniprot Name
Leukotriene B4 receptor 2
Molecular Weight
41524.35 Da
References
  1. Wang S, Gustafson E, Pang L, Qiao X, Behan J, Maguire M, Bayne M, Laz T: A novel hepatointestinal leukotriene B4 receptor. Cloning and functional characterization. J Biol Chem. 2000 Dec 29;275(52):40686-94. [PubMed:11006272]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Downie MM, Sanders DA, Maier LM, Stock DM, Kealey T: Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. Br J Dermatol. 2004 Oct;151(4):766-75. [PubMed:15491415]

Drug created on October 20, 2016 19:36 / Updated on November 02, 2018 07:32