We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Bovine Metabolome Database



Showing metabocard for 12-Keto-tetrahydro-leukotriene B4 (BMDB02995)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2006-05-22 16:12:25
Update Date 2009-05-05 20:59:36
Accession Number BMDB02995
Common Name 12-Keto-tetrahydro-leukotriene B4
Description 12-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 signaling pathways.
Synonyms
  1. 12-keto-10,11,14,15-tetrahydro-LTB4
  2. 5S-hydroxy-12-keto-6Z,8E-eicosadienoic acid
  3. 5S-hydroxy-12-keto-6Z,8E-eicosadienoate
Chemical IUPAC Name (5S,6Z,8E)-5-hydroxy-12-oxoicosa-6,8-dienoic acid
Chemical Formula C20H34O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Leukotrienes
Family
  • Mammalian_Metabolite
Species
  • ketone; secondary alcohol; carboxylic acid; alkene
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 338.482
Monoisotopic Molecular Weight 338.245697
Isomeric SMILES CCCCCCCCC(=O)CCC=CC=C/[C@@H](O)CCCC(O)=O
Canonical SMILES CCCCCCCCC(=O)CCC=CC=CC(O)CCCC(O)=O
KEGG Compound ID C02165 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 5283122 Link Image
PubChem Substance 4266072 Link Image
ChEBI ID 15647 Link Image
CAS Registry Number Not Available
InChI Identifier InChI=1/C20H34O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h7-8,11,15,19,22H,2-6,9-10,12-14,16-17H2,1H3,(H,23,24)/b8-7+,15-11-/t19-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.68e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity 3.58 Source: PhysProp
Predicted LogP/Hydrophobicity 4.8 [Predicted by PubChem via XLOGP]; 4.96 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental PDB File Show
Experimental PDB Structure
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
  • Membrane (Predicted from LogP)
Biofluid Location Not Available
Tissue Location
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available