You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2006-08-13 14:56:58 UTC
Update Date2017-12-20 20:32:50 UTC
Secondary Accession Numbers
  • HMDB0005086
  • HMDB04234
  • HMDB05086
Metabolite Identification
Common Name12-Keto-leukotriene B4
Description12-Keto-leukotriene B4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343 , 9667737 )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,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoic acidChEBI
12-Oxoleukotriene b4ChEBI
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acidChEBI
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoic acidChEBI
5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoic acidChEBI
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoic acidGenerator
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acidHMDB
12-dehydro-Leukotriene b4HMDB
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5S,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
Traditional Name12-oxo-LTB4
CAS Registry Number136696-10-1
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. 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
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Keto fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated ketone
  • Acryloyl-group
  • Enone
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Biological location:

  Cell and elements:



  Biofluid and excreta:

Route of exposure:




Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.884Not Available
Predicted Properties
Water Solubility0.0077 g/LALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.09 m³·mol⁻¹ChemAxon
Polarizability38.23 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, Positivesplash10-066s-8693000000-270563be8dfdc24e992aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-9144800000-4b327172349a2e771070View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0159000000-e48b7199180a29e45efbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-4492000000-f4f3d525c56b7199ffe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9550000000-602ab114fa3ef4af9e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-2b71bf068687ac05eecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-2679000000-f1fac0f3be2948f287f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9530000000-10303e21f4d2373a1b9dView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Acetaminophen Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Acetylsalicylic Acid Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Antipyrine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Antrafenine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Arachidonic Acid MetabolismThumbThumb?image type=greyscaleThumb?image type=simpleMap00590
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023341
KNApSAcK IDNot Available
Chemspider ID4444399
KEGG Compound IDC05949
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280876
PDB IDNot Available
ChEBI ID27814
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Powell WS, Rokach J, Khanapure SP, Manna S, Hashefi M, Gravel S, Macleod RJ, Falck JR, Bhatt RK: Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther. 1996 Feb;276(2):728-36. [PubMed:8632343 ]
  2. Primiano T, Li Y, Kensler TW, Trush MA, Sutter TR: Identification of dithiolethione-inducible gene-1 as a leukotriene B4 12-hydroxydehydrogenase: implications for chemoprevention. Carcinogenesis. 1998 Jun;19(6):999-1005. [PubMed:9667737 ]
  3. Lipid Maps (LMFA03020024) [Link]