Showing metabocard for 20-Hydroxy-leukotriene B4 (BMDB0001509)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:58 UTC
Update Date2020-05-21 16:27:00 UTC
BMDB IDBMDB0001509
Secondary Accession Numbers
  • BMDB01509
Metabolite Identification
Common Name20-Hydroxy-leukotriene B4
Description20-Hydroxy-leukotriene B4, also known as 20-OH-LTB4 or 20-hydroxy-LTB4, 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, 20-hydroxy-leukotriene B4 is considered to be an eicosanoid lipid molecule. 20-Hydroxy-leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoateChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoateChEBI
20-Hydroxy-LTB4ChEBI
20-OH-Leukotriene b4ChEBI
20-OH-LTB4ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoic acidGenerator
(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acidGenerator
(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoateHMDB
(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoic acidHMDB
(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoateHMDB
(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acidHMDB
20-Hydroxy LTB4HMDB
20-Hydroxyleukotriene b4HMDB
20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoateHMDB
20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoic acidHMDB
5,12,20-THETEHMDB
5,12,20-TriHETEHMDB
5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoateHMDB
5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acidHMDB
Omega-hydroxy-LTB4HMDB
W-Hydroxy-LTB4HMDB
[S-[R*,s*-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoateHMDB
[S-[R*,s*-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoic acidHMDB
20-Hydroxy-leukotriene bHMDB
5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acidHMDB
5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acid, (S-(r*,s*-(e,Z,e,Z)))-isomerHMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Name20-hydroxy-LTB4
CAS Registry Number79516-82-8
SMILES
OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1
InChI KeyPTJFJXLGRSTECQ-PSPARDEHSA-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
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • 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
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.22ALOGPS
logP2.69ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity104.91 m³·mol⁻¹ChemAxon
Polarizability40.46 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, Positivesplash10-00lj-3798000000-5bb085b2304969403378View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-7400967000-a9f5c76728347ea2738bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0009000000-2b98c651c0cd0833ccefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0009000000-a681c9193735a4386b49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0009000000-8db36dce15edb0d7b2f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udi-0109000000-e01ef44cb36e9df489f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0uea-0709000000-d7a7994b98cf3bfbe072View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0f8b-0924000000-bb49aa4e02bfea5085c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0il1-0910000000-8f7913074625390c6208View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0di9-0900000000-a87a75ca80ddc1745a1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0a4i-1900000000-972b13fd5c8b54c14aa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-fed023a2c990a5c6753fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1269000000-22fedd5f102230a634a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tp-6491000000-bfc9e7fd9147e861f375View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-e84044e33fbc237fabfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uei-1129000000-f307e44b0f4e538946e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9341000000-49f0ced38039afa26a80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-f4220ba5e589bf99a9eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1139000000-9334bf38981381cc7a00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002g-9532000000-8d635fd79d5a07bfbaa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9b61e666ea58e89197b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1229000000-f6625299fa9cf1f41bbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-6298000000-f0b013babab01e4ad7b8View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001509
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022663
KNApSAcK IDNot Available
Chemspider ID4444320
KEGG Compound IDC04853
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6287
PubChem Compound5280745
PDB IDNot Available
ChEBI ID15646
References
Synthesis ReferenceZamboni, Robert; Rokach, Joshua. Stereospecific synthesis of two metabolites of LTB4. Tetrahedron Letters (1982), 23(46), 4751-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A28
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A28
Uniprot ID:
P79102
Molecular weight:
58152.0
Reactions
6-trans-Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails