LBF20406LT13: Difference between revisions

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|LipidBank=XPR3301
|LipidBank=XPR3301
|LipidMaps=LMFA03020006
|LipidMaps=LMFA03020006
|SysName=5 (S) -Hydroxy-6 (R) -S-cysteinylglycinyleicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid
|SysName=5S-Hydroxy-6R-S-cysteinylglycinyl- (trans-7,trans-9,cis-11,cis-14) -eicosatetraenoic acid
|Common Name=&&LEUKOTRIENE D4&&5 (S) -Hydroxy-6 (R) -S-cysteinylglycinyleicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid&&
|Common Name=&&Leukotriene D_4&&5S-Hydroxy-6R-S-cysteinylglycinyl- (7E,9E,11Z,14Z) -eicosatetraenoic acid&&5 (S) -Hydroxy-6 (R) -S-cysteinylglycinyleicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid&&
|Solubility=METHANOL [[Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601|{{RelationTable/GetFirstAuthor|Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601}}]]
|Solubility=METHANOL [[Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601|{{RelationTable/GetFirstAuthor|Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601}}]]
|Mass Spectra=N-ACETYL, 5-TRIMETHYLSILYL ETHER DIMETHYL ESTER derivative ; 638(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 623, 607, 548, 508, 405, 404, 315, 314, 274, 273 [[Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601|{{RelationTable/GetFirstAuthor|Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601}}]]
|Mass Spectra=N-ACETYL, 5-TRIMETHYLSILYL ETHER DIMETHYL ESTER derivative ; 638(M^+ ), 623, 607, 548, 508, 405, 404, 315, 314, 274, 273 [[Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601|{{RelationTable/GetFirstAuthor|Reference:Morris_HR:Taylor_GW:Rokach_J:Girard_Y:Piper_PJ:Tippins_JR:Samhoun_MN:,Prostaglandins,1980,20,601}}]]
|UV Spectra=<FONT FACE="Symbol">l</FONT> <SUP><FONT SIZE=-1>M</FONT></SUP><SUP><FONT SIZE=-1>e</FONT></SUP><SUP><FONT SIZE=-1>O</FONT></SUP><SUP><FONT SIZE=-1>H</FONT></SUP><SUB><FONT SIZE=-1>m</FONT></SUB><SUB><FONT SIZE=-1>a</FONT></SUB><SUB><FONT SIZE=-1>x</FONT></SUB> = 270(<FONT FACE="Symbol">e</FONT> 32,000), 280(<FONT FACE="Symbol">e</FONT> 40,000), 290(<FONT FACE="Symbol">e</FONT> 31,000)nm [[Reference:Lewis_RA:Austen_KF:Drazen_JM:Clark_DA:Marfat_A:Corey_EJ:,Proc. Natl. Acad. Sci. U. S. A.,1980,77,3710|{{RelationTable/GetFirstAuthor|Reference:Lewis_RA:Austen_KF:Drazen_JM:Clark_DA:Marfat_A:Corey_EJ:,Proc. Natl. Acad. Sci. U. S. A.,1980,77,3710}}]]
|UV Spectra= lambda  ^{MeOH}_{max} = 270( epsilon  32,000), 280( epsilon  40,000), 290( epsilon  31,000)nm [[Reference:Lewis_RA:Austen_KF:Drazen_JM:Clark_DA:Marfat_A:Corey_EJ:,Proc. Natl. Acad. Sci. U. S. A.,1980,77,3710|{{RelationTable/GetFirstAuthor|Reference:Lewis_RA:Austen_KF:Drazen_JM:Clark_DA:Marfat_A:Corey_EJ:,Proc. Natl. Acad. Sci. U. S. A.,1980,77,3710}}]]
|Source=Leukotriene D4 is produced by basophils, eosinophils and macrophages of various animal species upon various stimulations on the cells [[Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1}}]][[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]].
|Source=Leukotriene D4 is produced by basophils, eosinophils and macrophages of various animal species upon various stimulations on the cells [[Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1}}]][[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]].
|Chemical Synthesis=[[Reference:Cohen_N:Banner_BL:Lopresti_RJ:Wong_F:Rosenberger_M:Liu_YY:Thom_E:Liebman_AA:,J. Am. Chem. Soc.,1983,105,3661|{{RelationTable/GetFirstAuthor|Reference:Cohen_N:Banner_BL:Lopresti_RJ:Wong_F:Rosenberger_M:Liu_YY:Thom_E:Liebman_AA:,J. Am. Chem. Soc.,1983,105,3661}}]] {{Image200|LBF20406LT13FT0001.gif}}
|Chemical Synthesis=[[Reference:Cohen_N:Banner_BL:Lopresti_RJ:Wong_F:Rosenberger_M:Liu_YY:Thom_E:Liebman_AA:,J. Am. Chem. Soc.,1983,105,3661|{{RelationTable/GetFirstAuthor|Reference:Cohen_N:Banner_BL:Lopresti_RJ:Wong_F:Rosenberger_M:Liu_YY:Thom_E:Liebman_AA:,J. Am. Chem. Soc.,1983,105,3661}}]] {{Image200|LBF20406LT13FT0001.gif}}
|Metabolism= <FONT FACE="Symbol">g</FONT>-Glutamyl transpeptidase hydrolyzes the glutathione moiety of leukotriene C4 and produces leukotriene D4 liberating glutamic acid [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]],
|Metabolism= gamma -Glutamyl transpeptidase hydrolyzes the glutathione moiety of leukotriene C4 and produces leukotriene D4 liberating glutamic acid [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]],
|Symbol=LTD4
|Biological Activity=Leukotriene D4 stimulates airway smooth muscles and causes bronchoconstriction. Vascular permeability is enhanced. Gasstrointestinal smooth muscles are contracted [[Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1}}]][[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]]. Leukotriene D4 binds to a receptor with 7 transmembrane domains coupled to Gi alpha /o protein (CysLT1) with an affinity higher by two orders of magnitude than that of leukotriene C4 [[Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789|{{RelationTable/GetFirstAuthor|Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789}}]].
|Genetic Information=cDNA for CysLT1 was cloned [[Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789|{{RelationTable/GetFirstAuthor|Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789}}]].
}}
 
{{MassbankSpectra|
UT000316
UT000317
UT000318
UT000319
UT000320
UT000321
UT000322
UT000323
UT000324
}}
}}


{{Lipid/Footer}}
{{Lipid/Footer}}

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



IDs and Links
LipidBank XPR3301
LipidMaps LMFA03020006
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406LT13
Leukotriene D4
LBF20406LT13.png
Structural Information
5S-Hydroxy-6R-S-cysteinylglycinyl- (trans-7,trans-9,cis-11,cis-14) -eicosatetraenoic acid
  • Leukotriene D4
  • 5S-Hydroxy-6R-S-cysteinylglycinyl- (7E,9E,11Z,14Z) -eicosatetraenoic acid
  • 5 (S) -Hydroxy-6 (R) -S-cysteinylglycinyleicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid
 LTD4
Formula C25H40N2O6S
Exact Mass 496.260707712
Average Mass 496.66098
SMILES C(=CC=CC=C[C@@H](SC[C@@H](C(=O)NCC(O)=O)N)[C@H](CCCC(O)=O)O)CC=CCCCCC
Physicochemical Information
METHANOL Morris_HR et al.
Leukotriene D4 is produced by basophils, eosinophils and macrophages of various animal species upon various stimulations on the cells Samuelsson_B et al. Hammarstrom_S .
Cohen_N et al.
LBF20406LT13FT0001.gif
 gamma -Glutamyl transpeptidase hydrolyzes the glutathione moiety of leukotriene C4 and produces leukotriene D4 liberating glutamic acid Hammarstrom_S ,
Leukotriene D4 stimulates airway smooth muscles and causes bronchoconstriction. Vascular permeability is enhanced. Gasstrointestinal smooth muscles are contracted Samuelsson_B et al. Hammarstrom_S . Leukotriene D4 binds to a receptor with 7 transmembrane domains coupled to Gi alpha /o protein (CysLT1) with an affinity higher by two orders of magnitude than that of leukotriene C4 Lynch_KR et al..
cDNA for CysLT1 was cloned Lynch_KR et al..
Spectral Information
Mass Spectra N-ACETYL, 5-TRIMETHYLSILYL ETHER DIMETHYL ESTER derivative ; 638(M+), 623, 607, 548, 508, 405, 404, 315, 314, 274, 273 Morris_HR et al.
UV Spectra λ MeOH
max     = 270( ε 32,000), 280( ε 40,000), 290( ε 31,000)nm Lewis_RA et al.
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406LT13 See above. Cohen_N et al. 1983
n.a. LBF20406LT13 See above. Hammarstrom_S 1983
n.a. LBF20406LT13 See above. Lewis_RA et al. 1980
n.a. LBF20406LT13 See above. Lynch_KR et al. 1999
n.a. LBF20406LT13 See above. Morris_HR et al. 1980
n.a. LBF20406LT13 See above. Samuelsson_B et al. 1982



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