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Record Information
StatusDetected and Quantified
Creation Date2007-04-12 21:41:01 UTC
Update Date2020-02-26 21:26:13 UTC
Secondary Accession Numbers
  • HMDB0004235
  • HMDB04235
  • HMDB06059
Metabolite Identification
Common Name20-Carboxy-leukotriene B4
Description20-Carboxyleukotriene B4 is an omega-oxidized metabolite of leukotriene B4 (LTB4). Neutrophil microsomes are known to oxidize 20-hydroxy-LTB4 (20-OH-LTB4) to its 20-oxo and 20-carboxy derivatives in the presence of NADPH. This activity has been ascribed to LTB4 omega-hydroxylase (cytochrome P-450LTB omega). Leukotriene B4 release from polymorphonuclear granulocytes of severely burned patients was reduced as compared to healthy donor cells. This decrease is due to an enhanced conversion of LTB4 into the 20-hydroxy- and 20-carboxy-metabolites and further to a decreased LTB4-synthesis. 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. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID 17623009 , 7633595 , 2155225 , 3039534 )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.
20-COOH-Leukotriene b4ChEBI
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioic acidChEBI
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioic acidGenerator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenedioic acidHMDB
(S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenedioic acidHMDB
20-Carboxy-leukotriene- b4HMDB
20-Carboxyleukotriene b4HMDB
20-Hydroxy-20-oxo-leukotriene b4HMDB
5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acidHMDB
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acidHMDB
Chemical FormulaC20H30O6
Average Molecular Weight366.4486
Monoisotopic Molecular Weight366.204238692
IUPAC Name(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid
Traditional Name20-cooh-LTB4
CAS Registry Number80434-82-8
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physiological effect

Health effect:


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
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.045 g/LALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity104.65 m³·mol⁻¹ChemAxon
Polarizability40.39 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, Positivesplash10-0005-2689000000-096c66447bfe6ad6733eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-002p-5210976000-f9a166749a4b77249360Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009000000-5550fddab03d6af2f102Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8j-0249000000-a2aa1fa4a5b39c1fd168Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw1-3493000000-1c97736464f35a64b096Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-e264ae86339bd5dedb96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4j-0119000000-c7065844077ceffef493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9242000000-99ba9a3a04c75f28044aSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified<0.001 uMAdult (>18 years old)Both
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000075 (0.0 - 0.000015) uMChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.0000025 (0.0 - 0.000005) umol/mmol creatinineChildren (1-13 years old)BothNormal details
Abnormal Concentrations
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000075 (0.0 - 0.000015) uMChildren (1-13 years old)BothSjögren-Larsson syndrome details
UrineDetected and Quantified0.0000025 (0.0 - 0.000005) umol/mmol creatinineChildren (1-13 years old)BothSjögren-Larsson syndrome details
Associated Disorders and Diseases
Disease References
Sjögren-Larsson syndrome
  1. Willemsen MA, Rotteveel JJ, de Jong JG, Wanders RJ, IJlst L, Hoffmann GF, Mayatepek E: Defective metabolism of leukotriene B4 in the Sjogren-Larsson syndrome. J Neurol Sci. 2001 Jan 15;183(1):61-7. [PubMed:11166796 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023824
KNApSAcK IDNot Available
Chemspider ID4444400
KEGG Compound IDC05950
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280877
PDB IDNot Available
ChEBI ID27562
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
  2. Yamane M, Shimizu S, Abe A, Sugiura H, Miyaoka M, Saitoh T: High-performance liquid chromatography-thermospray mass spectrometry of omega-carboxyleukotriene B4 and omega-hydroxyleukotriene B4 from an incubation mixture of human colonic well-differentiated adenocarcinoma homogenate. J Chromatogr B Biomed Appl. 1995 Apr 21;666(2):197-202. [PubMed:7633595 ]
  3. Sumimoto H, Minakami S: Oxidation of 20-hydroxyleukotriene B4 to 20-carboxyleukotriene B4 by human neutrophil microsomes. Role of aldehyde dehydrogenase and leukotriene B4 omega-hydroxylase (cytochrome P-450LTB omega) in leukotriene B4 omega-oxidation. J Biol Chem. 1990 Mar 15;265(8):4348-53. [PubMed:2155225 ]
  4. Brom J, Konig W, Koller M, Gross-Weege W, Erbs G, Muller F: Metabolism of leukotriene B4 by polymorphonuclear granulocytes of severely burned patients. Prostaglandins Leukot Med. 1987 May;27(2-3):209-25. [PubMed:3039534 ]
  5. Lipid Maps (LMFA03020016) [Link]