Record Information
Version1.0
Creation date2011-09-21 00:35:22 UTC
Update date2015-07-21 06:57:53 UTC
Primary IDFDB023824
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name20-Carboxyleukotriene B4
Description20-Carboxyleukotriene B4 is an omega-oxidized metabolite of leukotriene B4 (LTB4). Neutrophil microsomes are known to oxidize 20-hydroxy-LTB4 (20-OH-LTB4) to its 20-oxo and 20-carboxy derivatives in the presence of NADPH. This activity has been ascribed to LTB4 omega-hydroxylase (cytochrome P-450LTB omega). Leukotriene B4 release from polymorphonuclear granulocytes of severely burned patients was reduced as compared to healthy donor cells. This decrease is due to an enhanced conversion of LTB4 into the 20-hydroxy- and 20-carboxy-metabolites and further to a decreased LTB4-synthesis. 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. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID 17623009, 7633595, 2155225, 3039534) 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 Number80434-82-8
Structure
Thumb
Synonyms
SynonymSource
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioatehmdb
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acidhmdb
(S-(R*,S*-(E,Z,E,Z)))-5,12-dihydroxy-6,8,10,14-Eicosatetraenedioatehmdb
(S-(R*,S*-(E,Z,E,Z)))-5,12-dihydroxy-6,8,10,14-Eicosatetraenedioic acidhmdb
20-Carboxy-leukotriene B4hmdb
20-Carboxy-leukotriene- B4hmdb
20-carboxy-LTB4hmdb
20-COOH-Leukotriene B4hmdb
20-COOH-LTB4hmdb
20-hydroxy-20-oxo-leukotriene B4hmdb
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioatehmdb
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioic acidhmdb
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioateGenerator
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioic acidGenerator
5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoatehmdb
5(S),12(R)-Dihydroxy-20-carboxy-6,8,10,14-eicosatetraenoic acidhmdb
5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioatehmdb
5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraene-1,20-dioic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.17ALOGPS
logP2.81ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity104.65 m³·mol⁻¹ChemAxon
Polarizability42.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H30O6
IUPAC name(5S,8E,10E,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid
InChI IdentifierInChI=1S/C20H30O6/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/h2,4-8,12-13,17-18,21-22H,1,3,9-11,14-16H2,(H,23,24)(H,25,26)/b5-4+,6-2?,12-7+,13-8?/t17-,18-/m1/s1
InChI KeySXWGPVJGNOLNHT-FDPNBAIYSA-N
Isomeric SMILES[H][C@](O)(CCCC(O)=O)C=C\C=C\C=C\[C@]([H])(O)CC=CCCCCC(O)=O
Average Molecular Weight366.4486
Monoisotopic Molecular Weight366.204238692
Classification
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • 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 ID4444400
ChEMBL IDCHEMBL1592630
KEGG Compound IDC05950
Pubchem Compound ID5280877
Pubchem Substance IDNot Available
ChEBI ID27562
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06059
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