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Record Information
Version1.0
Creation Date2016-09-30 22:40:54 UTC
Update Date2020-05-11 20:44:23 UTC
BMDB IDBMDB0001085
Secondary Accession Numbers
  • BMDB01085
Metabolite Identification
Common NameLeukotriene B4
DescriptionLeukotriene B4, also known as LTB4 or 5,12-dihete, 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. Thus, leukotriene B4 is considered to be an eicosanoid lipid molecule. Leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acidChEBI
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acidChEBI
(S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acidChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acidChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoic acidChEBI
5,12-DiheteChEBI
5,12-HeteChEBI
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acidChEBI
LTB4ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoateKegg
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoateKegg
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoateGenerator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoateGenerator
(S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoateGenerator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoateGenerator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoateGenerator
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoateGenerator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acidGenerator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acidGenerator
5,12 HETEHMDB
5,12 DiHETEHMDB
Leukotriene b-4HMDB
Leukotrienes bHMDB
b-4, LeukotrieneHMDB
Leukotriene b 4HMDB
Leukotriene bHMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoateHMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acidHMDB
Leukotriene b4 ethanol solutionHMDB
(+)-Leukotriene b4HMDB
(5S,12R)-Leukotriene b4HMDB
5(S),12(R)-Dihydroxy-6-cis,8,10-trans,14-cis-eicosatetraenoic acidHMDB
Leucotriene b4HMDB
cis-Leukotriene b4HMDB
Leukotriene B4HMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number71160-24-2
SMILESNot Available
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-AMOLWHMGSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Epidermis
  • Leukocyte
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001085
DrugBank IDDB12961
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02165
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeukotriene_B4
METLIN IDNot Available
PubChem Compound5280492
PDB IDNot Available
ChEBI ID15647
References
Synthesis ReferenceHan, Chao Qi; DiTullio, Dennis; Wang, Yi Fong; Sih, Charles J. A chemoenzymatic synthesis of leukotriene B4. Journal of Organic Chemistry (1986), 51(8), 1253-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity (By similarity).
Gene Name:
LTA4H
Uniprot ID:
Q3SZH7
Molecular weight:
69306.0
General function:
Involved in G-protein coupled receptor protein signalin
Specific function:
Receptor for extracellular ATP > UTP and ADP. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. May be the cardiac P2Y receptor involved in the regulation of cardiac muscle contraction through modulation of L-type calcium currents. Is a receptor for leukotriene B4, a potent chemoattractant involved in inflammation and immune response (By similarity).
Gene Name:
LTB4R
Uniprot ID:
Q3T181
Molecular weight:
37689.0