LBF20306EO03: Difference between revisions

Latest revision as of 00:00, 21 January 2014

Upper classes: LB LBF

(+-) -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) Mosset_Pet 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) Mosset_Pet al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
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

@@ Line 4: / Line 4: @@
 {{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
+|Common Name=&&(+-) -11 (12) -Epoxy- (5Z,8Z,14Z) -eicosatrienoic acid&&11,12-EET&&
+|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=
+|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}}

IDs and Links
LipidBank	XPR6302 DFA8112, XPR6302
LipidMaps	LMFA03080004
CAS	81276-02-0
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}

mol	LBF20306EO03

LBF20306EO03: Difference between revisions

Latest revision as of 00:00, 21 January 2014

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