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Record Information
Version3.6
Creation Date2006-10-25 13:05:25 UTC
Update Date2016-02-11 01:07:04 UTC
HMDB IDHMDB05088
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-trans-12-epi-Leukotriene B4
Description6-trans-12-epi-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 , 17623009 , 2853166 , 6088485 ). 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
Synonyms
ValueSource
(5S,6E,8E,10E,12S,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acidChEBI
12-Epi-Delta(6)-trans-leukotriene b4ChEBI
5(S),12(S)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoic acidChEBI
5S,12S-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acidChEBI
5S,12S-Dihydroxy-6E,8E,10E,14Z-icosatetraenoic acidChEBI
6-trans-12-Epi-leukotriene b4ChEBI
6-trans-12-Epi-LTB4ChEBI
(5S,6E,8E,10E,12S,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoateGenerator
(5S,6E,8E,10E,12S,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoateGenerator
12-Epi-δ(6)-trans-leukotriene b4Generator
5(S),12(S)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoateGenerator
5S,12S-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoateGenerator
5S,12S-Dihydroxy-6E,8E,10E,14Z-icosatetraenoateGenerator
12-Epi-D6-trans-leukotriene b4HMDB
12-Epi-LTB4HMDB
D6-trans-12-Epi-LTB4HMDB
D6-trans-12-Epileukotriene b4HMDB
[S-[R*,r*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoateHMDB
[S-[R*,r*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6E,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Name6-trans-12-epi-LTB4
CAS Registry Number71548-19-1
SMILES
CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C\[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11+/t18-,19+/m0/s1
InChI KeyInChIKey=VNYSSYRCGWBHLG-CTOJTRLNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
Substituents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.58Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 mg/mLALOGPS
logP5.46ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m3·mol-1ChemAxon
Polarizability40.63 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.7E-5 +/- 3.7E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00022 +/- 7E-5 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023626
KNApSAcK IDNot Available
Chemspider ID4446253
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05088
Metagene LinkHMDB05088
METLIN IDNot Available
PubChem Compound5283129
PDB IDNot Available
ChEBI ID63982
References
Synthesis ReferenceNot 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. [7649996 ]
  2. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [17623009 ]
  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. [2853166 ]
  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. [6088485 ]
  5. Lipid Maps (LMFA03020014) [Link]