LBF20406LT17

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Upper classes: LB LBF



Leukotriene E4
LBF20406LT17.png
Structural Information
Systematic Name 5S-Hydroxy-6R-S-cysteinyl- (trans-7,trans-9,cis-11,cis-14) -eicosatetraenoic acid
Common Name
  • Leukotriene E4
  • 5S-Hydroxy-6R-S-cysteinyl- (7E,9E,11Z,14Z) -eicosatetraenoic acid
Symbol LTE4
Formula C23H37NO5S
Exact Mass 439.239243989
Average Mass 439.60962000000006
SMILES OC(=O)CCC[C@@H]([C@@H](C=CC=CC=CCC=CCCCCC)SC[C@H](N)C(O)=O)O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation DIMETHYL ESTER ; [ α ]20
D
   =+35.2° RosenbergerMet al.
Refractive Index
Solubility METHANOL RosenbergerMet al. CohenNet al.
Source When leukotriene C4 was injected into male subjects, leukotriene E4 was found as a major urinary metabolite Orning_L et al.. Incubation of leukotriene D4 with human polymorphonuclear leukocytes produced leukotriene E4 Lee_CW et al..
Chemical Synthesis Cohen_N et al.
LBF20406SF04FT0001.gif
Metabolism Leukotriene D4 is converted to E4 by extracellular action of a dipeptidase released from granules of human polymorphonuclear leukocytes Lee_CW et al.. Leukotriene E4 is transformed to leukotriene F4 by gamma -glultamyltransferase in the presence of glutathione, and to N-acetyl leukotriene E4 by incubation with rat liver microsomes Hammarstrom_S et al..
Biological Activity Leukotriene E4 stimulates airway smooth muscles from different animal species, and is less potent than C4 in contracting isolated guinea pig ileum Hammarstrom_S .
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra MONO-POTASSIUM SALT; λ = 270( ε 40000), 280( ε 49400), 291nm( ε 40000) CohenNet al.
IR Spectra
NMR Spectra DIMETHYL ESTER ; 1H-NMR(CDCl3) : δ 6.33(dd, J=14.5Hz, 10Hz, 1H, 10CH), 6.0(t, J=10Hz, 1H, 11-CH), 5.62(dd, J=14.4, 9.6Hz, 1H, 7-CH), 5.3(m, J=10,9Hz, 1H, 14-CH), 3.71 and 3.62(2S, 6H, OCH3), 3.65(m, 1H, 5-CH), 3.4(m, 1H, 6-CH), 2.95(t, J=9Hz, 2H, 13-CH), 2.02(m, 2H, 16-CH), 0.86(t, J=6Hz, 3H, 20-CH) RosenbergerMet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406LT17 See above. Hammarstrom_S 1983
n.a. LBF20406LT17 See above. Hammarstrom_S et al. 1985
n.a. LBF20406LT17 See above. Lee_CW et al. 1983
n.a. LBF20406LT17 See above. Orning_L et al. 1985
n.a. LBF20406LT17 See above. Rosenberger_M et al. 1983


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