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Showing Compound 12-Oxo-20-trihydroxy-leukotriene B4 (FDB029120)

Record Information
Version1.0
Creation date2011-09-21 01:50:25 UTC
Update date2015-07-21 06:59:38 UTC
Primary IDFDB029120
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name12-Oxo-20-trihydroxy-leukotriene B4
Description12-Oxo-20-trihydroxy-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human 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: 7649996, 17623009, 2853166, 6088485) 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 NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP2.12ALOGPS
logP2.34ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity107.09 m³·mol⁻¹ChemAxon
Polarizability41.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O7
IUPAC name(5R,6Z,8E,10E,14Z)-5,20,20,20-tetrahydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
InChI IdentifierInChI=1S/C20H30O7/c21-17(11-6-2-1-5-9-16-20(25,26)27)12-7-3-4-8-13-18(22)14-10-15-19(23)24/h2-4,6-8,12-13,18,22,25-27H,1,5,9-11,14-16H2,(H,23,24)/b4-3+,6-2-,12-7+,13-8-/t18-/m0/s1
InChI KeyQVZXILIWUPKGPA-CWJNPFRJSA-N
Isomeric SMILESO[C@H](CCCC(O)=O)\C=C/C=C/C=C/C(=O)C\C=C/CCCCC(O)(O)O
Average Molecular Weight382.448
Monoisotopic Molecular Weight382.199153314
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
  • Hydroxy fatty acid
  • Keto fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Ortho acid
  • Orthocarboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS12-Oxo-20-trihydroxy-leukotriene B4, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03xr-5695000000-f43c465a72aef1d7551dSpectrum
Predicted GC-MS12-Oxo-20-trihydroxy-leukotriene B4, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a59-5196088000-630f9e9946e77b93416aSpectrum
Predicted GC-MS12-Oxo-20-trihydroxy-leukotriene B4, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0009000000-370cbaa4b878ea6e18662017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1139000000-33a25aebafa6de3eb0d02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054n-8594000000-ce75714aff1cc93f043a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0009000000-77671d4ab98de689417e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03yi-1229000000-118d1440dd91de2b85502017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9131000000-1adf5d621a37ad5f60722017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0009000000-8fc21ac16316126326c82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-4129000000-c2bb1bddd8826f5b7fb52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9462000000-1176707efdbc2bb224532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0029000000-e0c54c582d1fdfcc62912021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0498000000-bc7eb9e531e9215e045b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ae9-7953000000-cd675cd408762f69e91a2021-09-23View Spectrum
NMRNot Available
ChemSpider ID30776629
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481460
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12553
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference