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Record Information
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:25 UTC
Update Date2020-02-26 21:24:20 UTC
Secondary Accession Numbers
  • HMDB02995
Metabolite Identification
Common Name12-Keto-tetrahydro-leukotriene B4
Description12-keto-tetrahydro-Leukotriene B4 is an inactivated enzymatic metabolite of leukotriene B4(LTB4), product of the human liver enzyme leukotriene B4 (LTB4) 12-hydroxydehydrogenase, also found in the porcine kidney and other mammals. 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: 17623009 , 8394361 , 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 signalling pathways.
5S-Hydroxy-12-keto-6Z,8E-eicosadienoic acidHMDB
Chemical FormulaC20H34O4
Average Molecular Weight338.4816
Monoisotopic Molecular Weight338.245709576
IUPAC Name(5S,6Z,8E)-5-hydroxy-12-oxoicosa-6,8-dienoic acid
Traditional Nameleukotriene B
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as other hydroxyeicosapolyenoic acids. These are hydroxyeicosapolyenoic acids which do not belong to the Hydroxyeicosapentaenoic acids, the Hydroxyeicosatetraenoic acids, or the Hydroxyeicosatrienoic acids.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentOther hydroxyeicosapolyenoic acids
Alternative Parents
  • Hydroxyeicosapolyenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Keto fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
LogP3.58Not Available
Predicted Properties
Water Solubility0.0067 g/LALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity99.88 m³·mol⁻¹ChemAxon
Polarizability41.03 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi4-8982000000-17057de07ae4d4492fc0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9125500000-270788ed45d1210a5cedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0019000000-6fc13279cd371fea9b4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0hbc-3595000000-77ffa7d42a1ed9c17ec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9650000000-0117916eb757427250d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-7581ef598d01fcad72b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0670-2569000000-4fe74a0ed76cc4e4ad6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9620000000-e99d688d13888f06c240Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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
FooDB IDFDB023093
KNApSAcK IDNot Available
Chemspider ID4446246
KEGG Compound IDC02165
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283122
PDB IDNot Available
ChEBI ID15647
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  5. Berry KA, Borgeat P, Gosselin J, Flamand L, Murphy RC: Urinary metabolites of leukotriene B4 in the human subject. J Biol Chem. 2003 Jul 4;278(27):24449-60. Epub 2003 Apr 22. [PubMed:12709426 ]
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  9. Costello PB, Baer AN, Green FA: Lipoxygenase products in inflammatory synovial fluids and other exudates. Ann Rheum Dis. 1992 Nov;51(11):1215-8. [PubMed:1334643 ]
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  11. Bentancur AG, Naveh N, Lancri J, Selah BA, Shtrasburg S, Livneh A: Urine leukotriene B4 in familial Mediterranean fever and other forms of right lower abdominal pain. Acad Emerg Med. 2005 Jul;12(7):671-4. [PubMed:15995103 ]
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  19. Merrill JE, Strom SR, Ellison GW, Myers LW: In vitro study of mediators of inflammation in multiple sclerosis. J Clin Immunol. 1989 Mar;9(2):84-96. [PubMed:2541163 ]
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  21. Johnson J, Meyrick B, Jesmok G, Brigham KL: Human recombinant tumor necrosis factor alpha infusion mimics endotoxemia in awake sheep. J Appl Physiol (1985). 1989 Mar;66(3):1448-54. [PubMed:2708260 ]
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  23. Dessein AJ, Lee TH, Elsas P, Ravalese J 3rd, Silberstein D, David JR, Austen KF, Lewis RA: Enhancement by monokines of leukotriene generation by human eosinophils and neutrophils stimulated with calcium ionophore A23187. J Immunol. 1986 May 15;136(10):3829-38. [PubMed:3009610 ]
  24. Romero R, Emamian M, Wan M, Grzyboski C, Hobbins JC, Mitchell MD: Increased concentrations of arachidonic acid lipoxygenase metabolites in amniotic fluid during parturition. Obstet Gynecol. 1987 Dec;70(6):849-51. [PubMed:3684118 ]
  25. Stenson WF, Lobos E: Sulfasalazine inhibits the synthesis of chemotactic lipids by neutrophils. J Clin Invest. 1982 Feb;69(2):494-7. [PubMed:6120182 ]
  26. Klickstein LB, Shapleigh C, Goetzl EJ: Lipoxygenation of arachidonic acid as a source of polymorphonuclear leukocyte chemotactic factors in synovial fluid and tissue in rheumatoid arthritis and spondyloarthritis. J Clin Invest. 1980 Nov;66(5):1166-70. [PubMed:6253525 ]
  27. Leppert D, Hauser SL, Kishiyama JL, An S, Zeng L, Goetzl EJ: Stimulation of matrix metalloproteinase-dependent migration of T cells by eicosanoids. FASEB J. 1995 Nov;9(14):1473-81. [PubMed:7589989 ]
  28. Shirazi Y, Rus HG, Macklin WB, Shin ML: Enhanced degradation of messenger RNA encoding myelin proteins by terminal complement complexes in oligodendrocytes. J Immunol. 1993 May 15;150(10):4581-90. [PubMed:7683324 ]
  29. Depre M, Friedman B, Van Hecken A, de Lepeleire I, Tanaka W, Dallob A, Shingo S, Porras A, Lin C, de Schepper PJ: Pharmacokinetics and pharmacodynamics of multiple oral doses of MK-0591, a 5-lipoxygenase-activating protein inhibitor. Clin Pharmacol Ther. 1994 Jul;56(1):22-30. [PubMed:8033491 ]
  30. Dias VC, Shaffer EA, Wallace JL, Parsons HG: Bile salts determine leukotriene B4 synthesis in a human intestinal cell line (CaCo-2). Dig Dis Sci. 1994 Apr;39(4):802-8. [PubMed:8149846 ]
  31. Iversen L, Fogh K, Ziboh VA, Kristensen P, Schmedes A, Kragballe K: Leukotriene B4 formation during human neutrophil keratinocyte interactions: evidence for transformation of leukotriene A4 by putative keratinocyte leukotriene A4 hydrolase. J Invest Dermatol. 1993 Mar;100(3):293-8. [PubMed:8382716 ]
  32. Matsuo M, Hamasaki Y, Masuyama T, Ohta M, Miyazaki S: Leukotriene B4 and C4 in cerebrospinal fluid from children with meningitis and febrile seizures. Pediatr Neurol. 1996 Feb;14(2):121-4. [PubMed:8703223 ]
  33. Takamoto M, Yano T, Shintani T, Hiraku S: A highly sensitive and selective method for the determination of Leukotriene B4 in human plasma by negative ion chemical ionization/gas chromatography/tandem mass spectrometry. J Pharm Biomed Anal. 1995 Nov;13(12):1465-72. [PubMed:8788131 ]
  34. Mozalevskii AF, Travianko TD, Iakovlev AA, Smirnova EA, Novikova NP, Sapa IIu: [Content of arachidonic acid metabolites in blood and saliva of children with bronchial asthma]. Ukr Biokhim Zh (1978). 1997 Sep-Dec;69(5-6):162-8. [PubMed:9606840 ]
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General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in binding
Specific function:
Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
Gene Name:
Uniprot ID:
Molecular weight: