LBF20406HO18: Difference between revisions

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|LipidBank=DFA8136
|LipidBank=DFA8136
|LipidMaps=LMFA03060008
|LipidMaps=LMFA03060008
|SysName=12R-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
|SysName=12R-Hydroxy- (cis-5,cis-8,trans-10,cis-14) -eicosatetraenoic acid
|Common Name=&&12R-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid&&
|Common Name=&&12R-Hydroxy- (5Z,8Z,10E,14Z) -eicosatetraenoic acid&&
|UV Spectra=lambdamax: 237nm epsilon: 27,000
|UV Spectra= lambda max: 237nm epsilon : 27,000
|Source=12(R)-HETE is produced by the action of 12(R)-lipoxygenase on arachidonic acid [[Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629|{{RelationTable/GetFirstAuthor|Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629}}]].
|Source=12(R)-HETE is produced by the action of 12(R)-lipoxygenase on arachidonic acid [[Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629|{{RelationTable/GetFirstAuthor|Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629}}]].
|Chemical Synthesis=
|Chemical Synthesis=
|Metabolism=12(R)-HETE is the predominant stereoisomer produced by psoriatic skin scales and rat liver microsomal cytochrome P-450 [[Reference:Woollard_PM:,Biochem. Biophys. Res. Commun.,1986,136,169|{{RelationTable/GetFirstAuthor|Reference:Woollard_PM:,Biochem. Biophys. Res. Commun.,1986,136,169}}]][[Reference:Capdevila_J:Yadagiri_P:Manna_S:Falck_JR:,Biochem. Biophys. Res. Commun.,1986,141,1007|{{RelationTable/GetFirstAuthor|Reference:Capdevila_J:Yadagiri_P:Manna_S:Falck_JR:,Biochem. Biophys. Res. Commun.,1986,141,1007}}]].
|Metabolism=12(R)-HETE is the predominant stereoisomer produced by psoriatic skin scales and rat liver microsomal cytochrome P-450 [[Reference:Woollard_PM:,Biochem. Biophys. Res. Commun.,1986,136,169|{{RelationTable/GetFirstAuthor|Reference:Woollard_PM:,Biochem. Biophys. Res. Commun.,1986,136,169}}]][[Reference:Capdevila_J:Yadagiri_P:Manna_S:Falck_JR:,Biochem. Biophys. Res. Commun.,1986,141,1007|{{RelationTable/GetFirstAuthor|Reference:Capdevila_J:Yadagiri_P:Manna_S:Falck_JR:,Biochem. Biophys. Res. Commun.,1986,141,1007}}]].
|Symbol=12(R)-HETE
|Symbol=12(R)-HETE
|Biological Activity=12(R)-HETE is the primary lipoxygenase product in invertebrates such as the sea urchin where it plays a role in reproduction physiology [[Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629|{{RelationTable/GetFirstAuthor|Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629}}]].1 12(R)-HETE has been isolated from several tissues in mammals, but it is controversial whether it is derived from cytochrome P450 or 12(R)-lipoxygenase metabolism, in some cases. 12(R)-HETE is a potent chemotactic factor exhibiting dose-dependent neutrophil chemotaxis with significant responses observed at doses as low as 10 ^- ^1 ^1  M [[Reference:Masferrer_JL:Rimarachin_JA:Gerritsen_ME:Falck_JR:Yadagiri_P:Dunn_MW:Laniado-Schwartzman_M:,Exp. Eye Res.,1991,52,417|{{RelationTable/GetFirstAuthor|Reference:Masferrer_JL:Rimarachin_JA:Gerritsen_ME:Falck_JR:Yadagiri_P:Dunn_MW:Laniado-Schwartzman_M:,Exp. Eye Res.,1991,52,417}}]]. It produces neovascularization in rabbit corneas at 0.5
|Biological Activity=12(R)-HETE is the primary lipoxygenase product in invertebrates such as the sea urchin where it plays a role in reproduction physiology [[Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629|{{RelationTable/GetFirstAuthor|Reference:Hawkins_DJ:Brash_AR:,J. Biol. Chem.,1987,262,7629}}]].1 12(R)-HETE has been isolated from several tissues in mammals, but it is controversial whether it is derived from cytochrome P450 or 12(R)-lipoxygenase metabolism, in some cases. 12(R)-HETE is a potent chemotactic factor exhibiting dose-dependent neutrophil chemotaxis with significant responses observed at doses as low as 10 ^{-11} M [[Reference:Masferrer_JL:Rimarachin_JA:Gerritsen_ME:Falck_JR:Yadagiri_P:Dunn_MW:Laniado-Schwartzman_M:,Exp. Eye Res.,1991,52,417|{{RelationTable/GetFirstAuthor|Reference:Masferrer_JL:Rimarachin_JA:Gerritsen_ME:Falck_JR:Yadagiri_P:Dunn_MW:Laniado-Schwartzman_M:,Exp. Eye Res.,1991,52,417}}]]. It produces neovascularization in rabbit corneas at 0.5 μg.
}}
}}


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Latest revision as of 07:27, 21 October 2010

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Upper classes: LB LBF



12R-Hydroxy- (5Z,8Z,10E,14Z) -eicosatetraenoic acid
LBF20406HO18.png
Structural Information
12R-Hydroxy- (cis-5,cis-8,trans-10,cis-14) -eicosatetraenoic acid
  • 12R-Hydroxy- (5Z,8Z,10E,14Z) -eicosatetraenoic acid
12(R)-HETE
Formula C20H32O3
Exact Mass 320.23514489
Average Mass 320.46628
SMILES C(CC=CCC(C=CC=CCC=CCCCC(O)=O)O)CCC
Physicochemical Information
12(R)-HETE is produced by the action of 12(R)-lipoxygenase on arachidonic acid Hawkins_DJ et al..
12(R)-HETE is the predominant stereoisomer produced by psoriatic skin scales and rat liver microsomal cytochrome P-450 Woollard_PM Capdevila_J et al..
12(R)-HETE is the primary lipoxygenase product in invertebrates such as the sea urchin where it plays a role in reproduction physiology Hawkins_DJ et al..1 12(R)-HETE has been isolated from several tissues in mammals, but it is controversial whether it is derived from cytochrome P450 or 12(R)-lipoxygenase metabolism, in some cases. 12(R)-HETE is a potent chemotactic factor exhibiting dose-dependent neutrophil chemotaxis with significant responses observed at doses as low as 10 ^{-11} M Masferrer_JL et al.. It produces neovascularization in rabbit corneas at 0.5 μg.
Spectral Information
Mass Spectra
UV Spectra λ max: 237nm ε : 27,000
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406HO18 See above. Capdevila_J et al. 1986
n.a. LBF20406HO18 See above. Hawkins_DJ et al. 1987
n.a. LBF20406HO18 See above. Lagarde_M et al. 1989
n.a. LBF20406HO18 See above. Masferrer_JL et al. 1991
n.a. LBF20406HO18 See above. Piomelli_D et al. 1989
n.a. LBF20406HO18 See above. Woollard_PM 1986