Showing metabocard for Leukotriene B4 (BMDB0001085)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
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
MOLSDFPDBSMILESInChI
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 Name(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Nameleukotriene B4
CAS Registry Number71160-24-2
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-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 Properties
PropertyValueSource
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
Polarizability39.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-7896000000-60973fb1d8ff05c73e4eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01rl-9113530000-205b0d713aeb42a9afc2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0419000000-061132d646cd5dd85a1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00ks-0829000000-7da7ab59ee0d4812767bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-0933000000-3fb381ce0f3609a90222View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-0931000000-ccfdaa3226146fe9edc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-1940000000-ef988be204f5c54f4b21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0r00-1910000000-e16cc958487f06dc4287View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0006-6900000000-a356f0334bf220eb54ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-052f-9700000000-66a6a217eba63b4874d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0a4l-7900000000-aeb350579ea4a84117d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0619000000-dc49d3f4ab097db18f18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-39d0f0947681f1f7fc37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-5498000000-4599d3006831091f926cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9450000000-b6647dcbb40f3175983dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0029000000-d2d2e17f68f90518361eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-2269000000-1a60fcc2f712b3beea2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9340000000-edfb4e3fd8a8f4667eadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-74962f74765b30de04acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-3659000000-98607094f1fa036e16e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5191000000-91a6c7d4dfff9bd70967View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-bbfb0bde6a04ea9b05bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3439000000-d8140c418a63ad2159a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-9320000000-afb563cb7a2b51e02836View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
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

Enzyme Details
1. Leukotriene A-4 hydrolase
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
Enzyme Details
2. Leukotriene B4 receptor 1
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