Record Information
Version1.0
Creation Date2016-05-27 01:05:00 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040927
Identification
Common Name10,11-Dihydro-20-dihydroxy-LTB4
ClassSmall Molecule
Description10,11-dihydro-20-dihydroxy-LTB4 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 signalling pathways.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(5S,12R,20)-Tetrahydroxy-(6Z,8E,14Z)-eicosatrienoateHMDB
(5S,12R,20)-Tetrahydroxy-(6Z,8E,14Z)-eicosatrienoic acidHMDB
10,11-Dihydroxy-20-dihydroxy-LTB(,4)HMDB
Chemical FormulaC20H34O6
Average Molecular Mass370.480 g/mol
Monoisotopic Mass370.236 g/mol
CAS Registry NumberNot Available
IUPAC Name(5R,6Z,8E,12R,14Z)-5,12,20,20-tetrahydroxyicosa-6,8,14-trienoic acid
Traditional Name(5R,6Z,8E,12R,14Z)-5,12,20,20-tetrahydroxyicosa-6,8,14-trienoic acid
SMILESOC(O)CCCC\C=C/C[C@H](O)CC\C=C\C=C/[C@H](O)CCCC(O)=O
InChI IdentifierInChI=1S/C20H34O6/c21-17(11-6-2-1-3-9-15-19(23)24)12-7-4-5-8-13-18(22)14-10-16-20(25)26/h2,4-6,8,13,17-19,21-24H,1,3,7,9-12,14-16H2,(H,25,26)/b5-4+,6-2-,13-8-/t17-,18-/m0/s1
InChI KeyBZDHSIPNZCHPKA-NSBXBVANSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carbonyl hydrate
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • 1,1-diol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.065 g/LALOGPS
logP3.5ALOGPS
logP2.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity105.09 m³·mol⁻¹ChemAxon
Polarizability42.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-3879000000-f1a551f0aff2c21651ecSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-006x-7557098000-c8448104d146aa593324Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0009000000-d1773c64d078e3a465ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-0139000000-e56a2d895f2ddf360a7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-6394000000-f7f149839344260a5c93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0009000000-562470dd30327396b824Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0009000000-c6e020ad15beac36d30eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-7489000000-2dcf1012d1dd3dc03820Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-6667c30358beab748272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0019000000-2e94b0d3fa9c78c5a953Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6297000000-6cbd470950fd44e7326fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0019000000-53c10464124c0b7a9e0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0169000000-7a326a63476017c7d806Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00u5-9420000000-1aa6fddc2dc3c4bfb8e9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012502
FooDB IDFDB029104
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776622
ChEBI IDNot Available
PubChem Compound ID53481447
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Powell WS, Rokach J, Khanapure SP, Manna S, Hashefi M, Gravel S, Macleod RJ, Falck JR, Bhatt RK: Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther. 1996 Feb;276(2):728-36.
2. Primiano T, Li Y, Kensler TW, Trush MA, Sutter TR: Identification of dithiolethione-inducible gene-1 as a leukotriene B4 12-hydroxydehydrogenase: implications for chemoprevention. Carcinogenesis. 1998 Jun;19(6):999-1005.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. The lipid handbook with CD-ROM