Delta(6)-trans,Delta(8)-cis-leukotriene B4 (YMDB00729)

Identification
YMDB IDYMDB00729
NameDelta(6)-trans,Delta(8)-cis-leukotriene B4
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDelta(6)-trans,Delta(8)-cis-leukotriene B4, also known as (6E,8Z)-LTB4 or δ(6)-trans,δ(8)-cis-LTB4, 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. Thus, Delta(6)-trans,Delta(8)-cis-leukotriene B4 is considered to be an eicosanoid lipid molecule. Delta(6)-trans,Delta(8)-cis-leukotriene B4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (5S,12R,6E,8Z,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid
  • (5S,6E,8Z,10E,12R,14Z)-5,12-dihydroxyeicosa-6,8,10,14-tetraenoic acid
  • (6E,8Z)-LTB4
  • 5,12-DiHETE
  • 5,12-dihydroxy-6,10-trans -8,14-cis -eicosatetraenoate
  • 5,12-dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acid
  • 5(S),12(R)-dihydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoic acid
  • 5(S),12(R)-dihydroxy-6(E),8(Z),10(E),14(Z)-icosatetraenoic acid
  • Acetic acid, iodo-
  • Delta(6)-trans,Delta(8)-cis-LTB4
  • Iodoacetic acid
  • leukotriene b4
  • leukotriene B4 ethanol solution
  • LTB4
  • (5S,12R,6E,8Z,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoate
  • (5S,6E,8Z,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate
  • 5(S),12(R)-Dihydroxy-6(e),8(Z),10(e),14(Z)-eicosatetraenoate
  • 5(S),12(R)-Dihydroxy-6(e),8(Z),10(e),14(Z)-icosatetraenoate
  • Δ(6)-trans,δ(8)-cis-LTB4
  • Δ(6)-trans,δ(8)-cis-leukotriene b4
  • (5S,6E,8Z,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoate
CAS numberNot Available
WeightAverage: 336.4657
Monoisotopic: 336.230059512
InChI KeyVNYSSYRCGWBHLG-GEWAPNICSA-N
InChIInChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7-,9-6-,14-10+,15-11+/t18-,19-/m1/s1
IUPAC Name(5S,6E,8Z,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional IUPAC Name(5S,6E,8Z,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Chemical FormulaC20H32O4
SMILESCCCCC\C=C/C[C@@H](O)\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O
Chemical Taxonomy
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
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP5.46ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability39.83 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • nucleus
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
leukotriene A4 + water ↔ Delta(6)-trans,Delta(8)-cis-leukotriene B4
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-7896000000-60973fb1d8ff05c73e4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-d06f0a12667843b97658JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-4497000000-49192078b0a92e5ed652JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9550000000-e2a30d40bfb9540f0c91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029000000-7cc4d5a37790281bbb77JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-2369000000-806fa56efb5d857c3921JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9350000000-bf1ddb92a7380f774742JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kull, F., Ohlson, E., Lind, B., Haeggstrom, J. Z. (2001). "Saccharomyces cerevisiae leukotriene A4 hydrolase: formation of leukotriene B4 and identification of catalytic residues." Biochemistry 40:12695-12703.11601994
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID53027
HMDB IDNot Available
Pubchem Compound ID9949656
Kegg IDNot Available
ChemSpider ID24608111
FOODB IDNot Available
WikipediaLeukotriene_B4
BioCyc IDNot Available

Enzymes

Protein Details
1. Leukotriene A-4 hydrolase
General function:
Involved in binding
Specific function:
Hydrolyzes an epoxide moiety of LTA(4) to form LTB(4). The enzyme also has aminopeptidase activity
Gene Name:
Not Available
Uniprot ID:
Q10740
Molecular weight:
77352.10156
Reactions
(7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H(2)O → (6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate.