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Record Information
StatusDetected and Quantified
Creation Date2006-10-25 08:58:52 UTC
Update Date2018-05-19 22:24:38 UTC
Secondary Accession Numbers
  • HMDB05073
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
5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acidMeSH
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 hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosapentaenoic acids
Alternative Parents
  • Hydroxyeicosapentaenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.895Not Available
Predicted Properties
Water Solubility0.016 g/LALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity104.1 m³·mol⁻¹ChemAxon
Polarizability38.28 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-5976000000-1308051082500b532d7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-002u-9114550000-fb98f8ad419bf0e2f1ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-001i-0009000000-9449fd58f9fde9620481View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-001i-0009000000-a9ad07c18d3c052b63acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-001i-0209000000-a818cc05c0ef95e2ad4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-001j-0829000000-0a8e49082c2592c2e26dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-0912000000-00b3332ca1c15daab105View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0gwb-0911000000-58f74003122760d3bd4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ir0-0900000000-d4d5e65bf183ee1dd84aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0dpi-2900000000-87002df340696b338906View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0abc-9800000000-487240d905b7a6f046a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0089000000-945a81862277ca8ffccdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kk-3492000000-1307f5bf34685a04ff67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-9550000000-dd3a21bd0ec9a9c3281bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0029000000-aea24fc310a30c0083f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-2359000000-2767c62677c595b5c621View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9440000000-c5ad6a89519cdea928caView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationNot 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
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023616
KNApSAcK IDNot Available
Chemspider ID4446249
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283125
PDB IDNot Available
ChEBI ID88493
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16424411 ]
  5. Lipid Maps (LMFA03020010) [Link]