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Showing metabocard for 12-Keto-leukotriene B4 (BMDB0004234)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:41 UTC
Update Date2020-04-22 15:13:33 UTC
BMDB IDBMDB0004234
Secondary Accession Numbers
  • BMDB04234
Metabolite Identification
Common Name12-Keto-leukotriene B4
Description12-Keto-leukotriene B4, also known as 12-keto-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, 12-keto-leukotriene B4 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 12-Keto-leukotriene B4.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoic acidChEBI
12-Keto-LTB4ChEBI
12-oxo-LTB4ChEBI
12-Oxoleukotriene b4ChEBI
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acidChEBI
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoic acidChEBI
5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoic acidChEBI
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoateGenerator
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoateGenerator
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoateGenerator
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoateGenerator
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoic acidGenerator
5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoateGenerator
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoateHMDB
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acidHMDB
12-Dehydro-leukotriene b4HMDB
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5S,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
Traditional Name12-oxo-LTB4
CAS Registry Number136696-10-1
SMILES
CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1
InChI KeySJVWVCVZWMJXOK-NOJHDUNKSA-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
  • Keto fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated ketone
  • Acryloyl-group
  • Enone
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.884Not Available
Predicted Properties
PropertyValueSource
logP4.67ALOGPS
logP4.54ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.09 m³·mol⁻¹ChemAxon
Polarizability38.23 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, Positivesplash10-066s-8693000000-270563be8dfdc24e992aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-9144800000-4b327172349a2e771070View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0159000000-e48b7199180a29e45efbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-4492000000-f4f3d525c56b7199ffe5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9550000000-602ab114fa3ef4af9e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-2b71bf068687ac05eecfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-2679000000-f1fac0f3be2948f287f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9530000000-10303e21f4d2373a1b9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0189000000-09dd2ea98a8fc120f55cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-3393000000-6fcc70d755077df7da3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9310000000-0661b8fef37b0dbab8c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-b749c60e47a942be0e50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05o0-3749000000-c3ef7aedfd2291dc938aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059l-5190000000-2e5d3124c6c577abd53bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004234
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023341
KNApSAcK IDNot Available
Chemspider ID4444399
KEGG Compound IDC05949
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280876
PDB IDNot Available
ChEBI ID27814
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available