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{{Metabolite
{{Metabolite
|LipidBank=DFA8112
|LipidBank=DFA8112, XPR6302
|LipidMaps=-
|LipidMaps=LMFA03080004
|SysName= (+-) 11 (12) -epoxy-5Z,8Z,14Z-eicosatrienoic acid
|CAS=81276-02-0
|Common Name=&&(+-) 11 (12) -epoxy-5Z,8Z,14Z-eicosatrienoic acid&&
|SysName=dl-11 (12) -Epoxy- (cis-5,cis-8,cis-14) -eicosatrienoic acid
|Source=(±)11(12)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 [[Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J. Biol. Chem.,1982,257,3771|{{RelationTable/GetFirstAuthor|Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J. Biol. Chem.,1982,257,3771}}]][[Reference:Chacos_N:Falck_JR:Wixtrom_C:Capdevila_J:,Biochem. Biophys. Res. Commun.,1982,104,916|{{RelationTable/GetFirstAuthor|Reference:Chacos_N:Falck_JR:Wixtrom_C:Capdevila_J:,Biochem. Biophys. Res. Commun.,1982,104,916}}]].
|Common Name=&&(+-) -11 (12) -Epoxy- (5Z,8Z,14Z) -eicosatrienoic acid&&11,12-EET&&
|Chemical Synthesis=
|Optical=11(R),12(S)-EET METHYL ESTER ; [ alpha ]^{23}_D=+4.94°(C=1.64, ACETONE) [[Reference:Mosset_P:Yadagiri_P:Lumin_S:Capdevila_J:Falck_JR:,Tetrahedron_Lett.,1986,27,6035|{{RelationTable/GetFirstAuthor|Reference:Mosset_P:Yadagiri_P:Lumin_S:Capdevila_J:Falck_JR:,Tetrahedron_Lett.,1986,27,6035}}]]<!--1098-->, 11(S),12(R)-EET METHYL ESTER ; [ alpha ]^{24}_D=-2.34°(C=0.66, CHLOROFORM) [[Reference:Falck_JR:Manna_S:Capdevila_J:,Tetrahedron_Lett.,1984,25,2443|{{RelationTable/GetFirstAuthor|Reference:Falck_JR:Manna_S:Capdevila_J:,Tetrahedron_Lett.,1984,25,2443}}]]<!--1099-->
|NMR Spectra=^1 H-NMR(CDCl3) : delta 5.54-5.20(m, 6H), 3.61(s, 3H), 3.00-2.68(m, 4H), 2.37-2.00(m, 10H), 1.81-1.54(m, 2H), 1.46-1.13(m, 6H), 0.88(t, J=7Hz, 3H) [[Reference:Mosset_P:Yadagiri_P:Lumin_S:Capdevila_J:Falck_JR:,Tetrahedron_Lett.,1986,27,6035|{{RelationTable/GetFirstAuthor|Reference:Mosset_P:Yadagiri_P:Lumin_S:Capdevila_J:Falck_JR:,Tetrahedron_Lett.,1986,27,6035}}]]<!--1098-->
|Mass Spectra=METHYL ESTER ; m/e 340(M^+ ), 322, 309, 227, 155 [[Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J._Biol._Chem.,1982,257,3771|{{RelationTable/GetFirstAuthor|Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J._Biol._Chem.,1982,257,3771}}]]<!--1096-->.
|Source=(±)11(12)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 [[Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J. Biol. Chem.,1982,257,3771|{{RelationTable/GetFirstAuthor|Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J. Biol. Chem.,1982,257,3771}}]][[Reference:Chacos_N:Falck_JR:Wixtrom_C:Capdevila_J:,Biochem. Biophys. Res. Commun.,1982,104,916|{{RelationTable/GetFirstAuthor|Reference:Chacos_N:Falck_JR:Wixtrom_C:Capdevila_J:,Biochem. Biophys. Res. Commun.,1982,104,916}}]]. The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat [[Reference:Chacos_N:Falck_JR:Wixtrom_C:Capdevila_J:,Biochem._Biophys._Res._Commun.,1982,104,916|{{RelationTable/GetFirstAuthor|Reference:Chacos_N:Falck_JR:Wixtrom_C:Capdevila_J:,Biochem._Biophys._Res._Commun.,1982,104,916}}]]<!--0076--> or rabbit [[Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J._Biol._Chem.,1982,257,3771|{{RelationTable/GetFirstAuthor|Reference:Oliw_EH:Guengerich_FP:Oates_JA:,J._Biol._Chem.,1982,257,3771}}]]<!--0077-->
|Chemical Synthesis=[http://lipidbank.jp/image/XPR6302FT0001.gif Table0001] [[Reference:Mosset_P:Yadagiri_P:Lumin_S:Capdevila_J:Falck_JR:,Tetrahedron_Lett.,1986,27,6035|{{RelationTable/GetFirstAuthor|Reference:Mosset_P:Yadagiri_P:Lumin_S:Capdevila_J:Falck_JR:,Tetrahedron_Lett.,1986,27,6035}}]]<!--1098-->
|Metabolism=
|Metabolism=
|Symbol=(+-)11(12)-EpETrE
|Biological Activity=(±)11(12)-EpETrE has been shown, along with (±)8(9)-EpETrE, to play a role in the recovery of depleted Ca^{2+} pools in cultured smooth muscle cells [[Reference:Graber_MN:Alfonso_A:Gill_DL:,J. Biol. Chem.,1997,272,29546|{{RelationTable/GetFirstAuthor|Reference:Graber_MN:Alfonso_A:Gill_DL:,J. Biol. Chem.,1997,272,29546}}]]. The compound relaxes intestinal artery, inhibits vasopressin-dependent water flow in urinary bladder, and regulates intracellular calcium level [[Reference:Fitzpatrick_FA:Murphy_RC:,Pharmacol._Rev.,1988,40,229|{{RelationTable/GetFirstAuthor|Reference:Fitzpatrick_FA:Murphy_RC:,Pharmacol._Rev.,1988,40,229}}]]<!--0078-->.
}}
{{MassbankSpectra|
UT000001
UT000002
UT000003
UT000004
UT000005
UT000006
UT000007
UT000008
UT000009
}}
}}


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

Latest revision as of 09:00, 21 January 2014

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Upper classes: LB LBF



IDs and Links
LipidBank XPR6302 DFA8112, XPR6302
LipidMaps LMFA03080004
CAS 81276-02-0
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20306EO03
(+-) -11 (12) -Epoxy- (5Z,8Z,14Z) -eicosatrienoic acid
Structural Information
dl-11 (12) -Epoxy- (cis-5,cis-8,cis-14) -eicosatrienoic acid
  • (+-) -11 (12) -Epoxy- (5Z,8Z,14Z) -eicosatrienoic acid
  • 11,12-EET
 (+-)11(12)-EpETrE
Formula C20H32O3
Exact Mass 320.23514489
Average Mass 320.46628
SMILES C(CC=CCC(O1)C1CC=CCC=CCCCC(O)=O)CCC
Physicochemical Information
11(R),12(S)-EET METHYL ESTER ; [ α ]23
D  =+4.94°(C=1.64, ACETONE) MossetPet al., 11(S),12(R)-EET METHYL ESTER ; [ α ]24
D  =-2.34°(C=0.66, CHLOROFORM) Falck_JR et al.
(±)11(12)-EpETrE is biosynthesized in rat and rabbit liver microsomes by cytochrome P450 Oliw_EH et al. Chacos_N et al.. The compound is produced when arachidonic acid in the presence of NADPH is incubated with the liver microsome of rat Chacos_N et al. or rabbit Oliw_EH et al.
Table0001 Mosset_P et al.
(±)11(12)-EpETrE has been shown, along with (±)8(9)-EpETrE, to play a role in the recovery of depleted Ca^{2+} pools in cultured smooth muscle cells Graber_MN et al.. The compound relaxes intestinal artery, inhibits vasopressin-dependent water flow in urinary bladder, and regulates intracellular calcium level Fitzpatrick_FA et al..
Spectral Information
Mass Spectra METHYL ESTER ; m/e 340(M+), 322, 309, 227, 155 Oliw_EH et al..
UV Spectra
IR Spectra
NMR Spectra 1H-NMR(CDCl3) : δ 5.54-5.20(m, 6H), 3.61(s, 3H), 3.00-2.68(m, 4H), 2.37-2.00(m, 10H), 1.81-1.54(m, 2H), 1.46-1.13(m, 6H), 0.88(t, J=7Hz, 3H) MossetPet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20306EO03 See above. Chacos_N et al. 1982
n.a. LBF20306EO03 See above. Falck_JR et al. 1984
n.a. LBF20306EO03 See above. Fitzpatrick_FA et al. 1988
n.a. LBF20306EO03 See above. Graber_MN et al. 1997
n.a. LBF20306EO03 See above. Mosset_P et al. 1986
n.a. LBF20306EO03 See above. Oliw_EH et al. 1982



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