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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-25 12:50:12 UTC
Update Date2020-02-26 21:25:45 UTC
HMDB IDHMDB0005087
Secondary Accession Numbers
  • HMDB0010218
  • HMDB05087
  • HMDB10218
Metabolite Identification
Common Name6-trans-Leukotriene B4
Description6-trans-Leukotriene B4 is an enzymatic metabolite of leukotriene B4(LTB4). A greater increase in LTB4 and 6-trans-LTB4 (one of its hydroxylated 5-lipoxygenase metabolic derivatives) occurs after stimulation with calcium-ionophore in asthma patients compared to healthy controls. 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 omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation (PMID: 17623009 , 2176862 , 7649996 , 9667737 , 2125732 ). 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.
Structure
Data?1582752344
Synonyms
ValueSource
(5S,6E,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acidChEBI
(6E,5S,12R)-Leukotriene b4ChEBI
5(S),12(R)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoic acidChEBI
5S,12R-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acidChEBI
5S,12R-Dihydroxy-6E,8E,10E,14Z-icosatetraenoic acidChEBI
6-trans-LTB4ChEBI
Delta(6)-trans-Leukotriene b4ChEBI
Delta(6)-trans-LT b4ChEBI
(5S,6E,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoateGenerator
5(S),12(R)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoateGenerator
5S,12R-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoateGenerator
5S,12R-Dihydroxy-6E,8E,10E,14Z-icosatetraenoateGenerator
Δ(6)-trans-leukotriene b4Generator
Δ(6)-trans-LT b4Generator
D6-trans-Leukotriene b4HMDB
D6-trans-LTB4HMDB
[S-[R*,s*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoateHMDB
[S-[R*,s*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acidHMDB
delta6-trans-LTB4HMDB
delta6-trans-Leukotriene b4HMDB
Δ6-trans-LTB4HMDB
Δ6-trans-leukotriene b4HMDB
6-trans-Leukotriene B4HMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6E,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Name6-trans-LTB4
CAS Registry Number71652-82-9
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-/m1/s1
InChI KeyVNYSSYRCGWBHLG-UKNWISKWSA-N
Chemical Taxonomy
Description 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. 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
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability40.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-7896000000-782d01776a33cc451555Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01rl-9113530000-205b0d713aeb42a9afc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0419000000-061132d646cd5dd85a1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00ks-0829000000-7da7ab59ee0d4812767bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-0933000000-3fb381ce0f3609a90222Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-0931000000-ccfdaa3226146fe9edc3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-1940000000-ef988be204f5c54f4b21Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0r00-1910000000-e16cc958487f06dc4287Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0006-6900000000-a356f0334bf220eb54ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-052f-9700000000-66a6a217eba63b4874d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0a4l-7900000000-aeb350579ea4a84117d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0619000000-dc49d3f4ab097db18f18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-69c64ad7b55da6a633e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-5598000000-0a1483f60114546ce2c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9550000000-0ad5f1d400a5ff275f25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0029000000-0164a507a03180713a2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-2269000000-52f6b9d4ecc4e26ff1feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9340000000-c2e72464c072384447e0Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00011 +/- 0.00003 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000223 +/- 0.000042 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.000223 +/- 0.000042 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022416
KNApSAcK IDNot Available
Chemspider ID4446252
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeukotriene B4
METLIN IDNot Available
PubChem Compound5283128
PDB IDNot Available
ChEBI ID63981
Food Biomarker OntologyNot Available
VMH IDCE2445
References
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. Wainwright S, Falck JR, Yadagiri P, Powell WS: Metabolism of 12(S)-hydroxy-5,8,10,14-eicosatetraenoic acid and other hydroxylated fatty acids by the reductase pathway in porcine polymorphonuclear leukocytes. Biochemistry. 1990 Oct 30;29(43):10126-35. [PubMed:2176862 ]
  3. 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 ]
  4. Primiano T, Li Y, Kensler TW, Trush MA, Sutter TR: Identification of dithiolethione-inducible gene-1 as a leukotriene B4 12-hydroxydehydrogenase: implications for chemoprevention. Carcinogenesis. 1998 Jun;19(6):999-1005. [PubMed:9667737 ]
  5. Radeau T, Chavis C, Damon M, Michel FB, Crastes de Paulet A, Godard PH: Enhanced arachidonic acid metabolism and human neutrophil migration in asthma. Prostaglandins Leukot Essent Fatty Acids. 1990 Oct;41(2):131-8. [PubMed:2125732 ]