20-Carboxy-leukotriene B4 (CHEM021706)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:29 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021706
Identification
Common Name20-Carboxy-leukotriene B4
ClassSmall Molecule
DescriptionA member of the class of leukotrienes that is leukotriene B4 in which the terminal methyl group has undergone formal oxidation to the corresponding carboxylic acid.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
20-Carboxy-LTB4ChEBI
20-COOH-Leukotriene b4ChEBI
20-COOH-LTB4ChEBI
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioic acidChEBI
5,12-Dihydroxy-delta5,8,11,14-eicosapolyendioateGenerator
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioateGenerator
5,12-Dihydroxy-δ5,8,11,14-eicosapolyendioic acidGenerator
(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-Carboxyleukotriene b4HMDB
20-Hydroxy-20-oxo-leukotriene b4HMDB
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
20-COOH LTB4HMDB
Chemical FormulaC20H30O6
Average Molecular Mass366.449 g/mol
Monoisotopic Mass366.204 g/mol
CAS Registry Number80434-82-8
IUPAC Name(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenedioic acid
Traditional Name20-cooh-LTB4
SMILESO[C@@H](CCCC(O)=O)\C=C/C=C/C=C/[C@H](O)C\C=C/CCCCC(O)=O
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-VFLUTPEKSA-N
Chemical Taxonomy
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 Descriptors
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 Solubility0.045 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
Polarizability40.39 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, Positivesplash10-0005-2689000000-096c66447bfe6ad6733eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-002p-5210976000-f9a166749a4b77249360Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009000000-5550fddab03d6af2f102Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8j-0249000000-a2aa1fa4a5b39c1fd168Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw1-3493000000-1c97736464f35a64b096Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-e264ae86339bd5dedb96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4j-0119000000-c7065844077ceffef493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9242000000-99ba9a3a04c75f28044aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-0009000000-a987ee79162f85ff16ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-3039000000-233d80f7f111963e8f18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9552000000-821cd0bc697d2333645fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0029000000-a8397c4233da39a13193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053s-1096000000-4ced9dcb2b61dd57a14dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0570-9371000000-48100671499945ded827Spectrum
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 IDHMDB0006059
FooDB IDFDB112228
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444400
ChEBI ID27562
PubChem Compound ID5280877
Kegg Compound IDC05950
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95.
2. Yamane M, Shimizu S, Abe A, Sugiura H, Miyaoka M, Saitoh T: High-performance liquid chromatography-thermospray mass spectrometry of omega-carboxyleukotriene B4 and omega-hydroxyleukotriene B4 from an incubation mixture of human colonic well-differentiated adenocarcinoma homogenate. J Chromatogr B Biomed Appl. 1995 Apr 21;666(2):197-202.
3. Sumimoto H, Minakami S: Oxidation of 20-hydroxyleukotriene B4 to 20-carboxyleukotriene B4 by human neutrophil microsomes. Role of aldehyde dehydrogenase and leukotriene B4 omega-hydroxylase (cytochrome P-450LTB omega) in leukotriene B4 omega-oxidation. J Biol Chem. 1990 Mar 15;265(8):4348-53.
4. Brom J, Konig W, Koller M, Gross-Weege W, Erbs G, Muller F: Metabolism of leukotriene B4 by polymorphonuclear granulocytes of severely burned patients. Prostaglandins Leukot Med. 1987 May;27(2-3):209-25.
5. Lipid Maps (LMFA03020016): http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA03020016