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Human Metabolome Database Version 2.5

 

Showing metabocard for 20-Carboxyleukotriene B4 (HMDB06059)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2007-04-12 22:41:01
Update Date 2009-05-05 21:00:49
Accession Number HMDB06059
Secondary Accession Numbers HMDB04235
Common Name 20-Carboxyleukotriene B4
Description 20-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 signaling pathways.
Synonyms
  1. 20-Carboxy-leukotriene B4
  2. 20-Carboxy-leukotriene- B4
  3. 20-carboxy-LTB4
  4. 20-carboxyleukotriene B4
  5. 20-COOH-Leukotriene B4
  6. 20-COOH-LTB4
  7. 20-hydroxy-20-oxo-leukotriene B4
  8. 5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acid
  9. 5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioic acid
  10. 5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acid
  11. (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid
  12. (S-(R*,S*-(E,Z,E,Z)))-5,12-dihydroxy-6,8,10,14-Eicosatetraenedioic acid
  13. 5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoate
  14. 5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioate
  15. 5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioate
  16. (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioate
  17. (S-(R*,S*-(E,Z,E,Z)))-5,12-dihydroxy-6,8,10,14-Eicosatetraenedioate
Chemical IUPAC Name (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid
Chemical Formula C20H30O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Leukotrienes
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 366.449
Monoisotopic Molecular Weight 366.204254
Isomeric SMILES O[C@@H](CCCC(O)=O)C=C/C=C/C=C/[C@H](O)CC=C/CCCCC(O)=O
Canonical SMILES OC(CCCC(O)=O)C=CC=CC=CC(O)CC=CCCCCC(O)=O
KEGG Compound ID C05950 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06059 Link Image
Metagene Link HMDB06059 Link Image
METLIN ID Not Available
PubChem Compound 5280877 Link Image
PubChem Substance 8616417 Link Image
ChEBI ID 27562 Link Image
CAS Registry Number 80434-82-8
InChI Identifier InChI=1/C20H30O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2-,12-7+,13-8-/t17-,18-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0454 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.17 [Predicted by ALOGPS]; 2.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Cerebrospinal Fluid
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid CSF
Value 0.0000075 (0.0 - 0.000015) uM
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.0000025 (0.0 - 0.000005) umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Concentrations (Abnormal)
Biofluid CSF
Value 0.0000075 (0.0 - 0.000015) uM
Age Children:1-13 yrs old
Sex Both
Condition Sjögren-Larsson syndrome
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 0.0000025 (0.0 - 0.000005) umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Condition Sjögren-Larsson syndrome
Comments Not Available
References
  • 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 Link Image]
Associated Disorders
Condition References
Sjögren-Larsson syndrome
  • 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 Link Image]
OMIM ID
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 Link Image map00590 Link Image
General References
  1. LMFA03020016