Human Metabolome Database Version 3.5

Showing metabocard for 12-Oxo-20-hydroxy-leukotriene B4 (HMDB12552)

Record Information
Version 3.5
Creation Date 2009-07-24 18:02:47 -0600
Update Date 2013-05-29 13:48:13 -0600
HMDB ID HMDB12552
Secondary Accession Numbers None
Metabolite Identification
Common Name 12-Oxo-20-hydroxy-leukotriene B4
Description 12-oxo-20-hydroxy-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human 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: 7649996 Link_out, 17623009 Link_out, 2853166 Link_out, 6088485 Link_out). 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.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. (5S,20)-dihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoate
  2. (5S,20)-dihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoic acid
  3. (5S,20)-dihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoate
  4. (5S,20)-dihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoic acid
  5. 12-Keto-20-hydroxy-leukotriene B(,4)
  6. Ox20HLTB4
Chemical Formula C20H30O5
Average Molecular Weight 350.4492
Monoisotopic Molecular Weight 350.20932407
IUPAC Name (5R,6Z,8E,10E,14Z)-5,20-dihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
Traditional IUPAC Name (5R,6Z,8E,10E,14Z)-5,20-dihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
CAS Registry Number Not Available
SMILES OCCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@H](O)CCCC(O)=O
InChI Identifier InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,19,21,23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t19-/m0/s1
InChI Key CZWPUWRHQBAXJS-PABROBRYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Other Hydroxyeicosapolyenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Keto Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acryloyl Group
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid Salt
  • Enone
  • Fatty Alcohol
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Other Hydroxyeicosapolyenoic Acids
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.027 g/L ALOGPS
LogP 3.48 ALOGPS
LogP 3.1 ChemAxon
LogS -4.11 ALOGPS
pKa (strongest acidic) 4.65 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 104.02 ChemAxon
Polarizability 39.84 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029119
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12552 Link_out
Metagene Link HMDB12552 Link_out
METLIN ID Not Available
PubChem Compound 53481459 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Wheelan P, Murphy RC: Metabolism of 6-trans-isomers of leukotriene B4 in cultured hepatoma cells and in human polymorphonuclear leukocytes. Identification of a delta 6-reductase metabolic pathway. J Biol Chem. 1995 Aug 25;270(34):19845-52. Pubmed: 7649996 Link_out
  2. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. Pubmed: 17623009 Link_out
  3. Mita H, Yui Y, Yasueda H, Shida T: Isocratic determination of arachidonic acid 5-lipoxygenase products in human neutrophils by high-performance liquid chromatography. J Chromatogr. 1988 Sep 9;430(2):299-308. Pubmed: 2853166 Link_out
  4. Shak S, Goldstein IM: Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. J Biol Chem. 1984 Aug 25;259(16):10181-7. Pubmed: 6088485 Link_out