Record Information
Version1.0
Creation date2011-09-21 00:28:22 UTC
Update date2015-07-21 06:57:39 UTC
Primary IDFDB023341
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name12-Keto-leukotriene B4
Description12-Keto-leukotriene B4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. 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 w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343, 9667737) 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 signaling pathways. [HMDB]
CAS Number136696-10-1
Structure
Thumb
Synonyms
SynonymSource
12-Oxoleukotriene b4MeSH
12-oxo-LTB4MeSH
(5S,6Z,8e,10e,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoateGenerator
(5S,6Z,8e,10e,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoic acidChEBI
(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
12-Keto-LTB4hmdb
12-Oxo-ltb4hmdb
12-Oxoleukotriene B4hmdb
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoatehmdb
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoic acidhmdb
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoateGenerator
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoic acidGenerator
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoateGenerator
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acidChEBI
5S-hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoatehmdb
5S-hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0077 g/LALOGPS
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
Polarizability39.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H30O4
IUPAC name(5S)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
InChI IdentifierInChI=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)/t19-/m1/s1
InChI KeySJVWVCVZWMJXOK-LJQANCHMSA-N
Isomeric SMILES[H][C@](O)(CCCC(O)=O)C=CC=CC=CC(=O)CC=CCCCCC
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
Classification
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
  • Keto fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4444399
ChEMBL IDNot Available
KEGG Compound IDC05949
Pubchem Compound ID5280876
Pubchem Substance IDNot Available
ChEBI ID27814
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04234
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference