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Record Information
Creation Date2006-10-25 08:58:52 UTC
Update Date2016-02-11 01:07:03 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameLeukotriene B5
DescriptionLeukotriene B5 (LTB5) is a 5-lipoxygenase metabolite of arachidonic (AA) and eicosapentaenoic acid (EPA), involved in numerous inflammatory diseases and possesses a substantially less potent inflammatory effect than LTB4. Binding of LTB5 to human neutrophil LTB4 high affinity binding sites is lower than that of LTB4. Polymorphonuclear leukocytes isolated from volunteers who ingested eicosapentaenoic acid (EPA) form LTB5. Enrichment of human neutrophils with EPA, by dietary supplementation for at least 3 weeks, reduces their formation of LTB4 ex vivo. LTB5 is catabolized to 20-OH-LTB5, which in turn is metabolized to 20-COOH-LTB5. Presumably the same enzyme systems are involved in the catabolism of LTB5 that are responsible for catabolism of LTB4. Fish oil supplementation has a protective effect on exercise-induced bronchoconstriction (EIB) in elite athletes, which may be attributed to its antiinflammatory properties due to a significant reduction in LTB4 and a significant increase in LTB5 generation from activated polymorphonuclear leukocytes (PMNLs). (PMID: 1964169 , 15866528 , 2538061 , 16424411 ). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways.
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acidHMDB
5,12-Dihydroxy-6-trans-leukotriene b(5)HMDB
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5S,6Z,8E,10E,12R,14Z,17Z)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid
Traditional Nameleukotriene B5
CAS Registry Number80445-66-5
InChI Identifier
Chemical Taxonomy
DescriptionThis 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. 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
  • Leukotriene
  • Hydroxyeicosapentaenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.895Not Available
Predicted Properties
Water Solubility0.016 mg/mLALOGPS
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 Count13ChemAxon
Refractivity104.1 m3·mol-1ChemAxon
Polarizability38.28 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.000079 +/- 0.000006 uMAdult (>18 years old)Both
BloodDetected and Quantified0.000079 +/- 0.0000056 uMAdult (>18 years old)Both
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023616
KNApSAcK IDNot Available
Chemspider ID4446249
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05073
Metagene LinkHMDB05073
METLIN IDNot Available
PubChem Compound5283125
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. von Schacky C, Fahrer C, Fischer S: Catabolism of leukotriene B5 in humans. J Lipid Res. 1990 Oct;31(10):1831-8. [1964169 ]
  2. Panchaud A, Avois L, Roulet M, Pilet M, Hug C, Saugy M, Decosterd LA: A validated liquid chromatography-mass spectrometry method for the determination of leukotrienes B4 and B5 produced by stimulated human polymorphonuclear leukocytes. Anal Biochem. 2005 Jun 1;341(1):58-68. [15866528 ]
  3. Heidel JR, Taylor SM, Laegreid WW, Silflow RM, Liggitt HD, Leid RW: In vivo chemotaxis of bovine neutrophils induced by 5-lipoxygenase metabolites of arachidonic and eicosapentaenoic acid. Am J Pathol. 1989 Mar;134(3):671-6. [2538061 ]
  4. Mickleborough TD, Lindley MR, Ionescu AA, Fly AD: Protective effect of fish oil supplementation on exercise-induced bronchoconstriction in asthma. Chest. 2006 Jan;129(1):39-49. [16424411 ]
  5. Lipid Maps (LMFA03020010) [Link]