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{{Lipid/Header}}
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|LipidBank=XPR1411
|LipidBank=XPR1411
|LipidMaps=LMFA03010030
|LipidMaps=LMFA03010030
|SysName=7- [ 3 (R) -Hydroxy-2 (R) - (3-oxo-1 (E) -octenyl) -5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
|SysName=7- [3R -Hydroxy-2R - (3-oxo-trans-1-octenyl) -5-oxocyclopentan-1R -yl] -cis-5-heptenoic acid
|Common Name=&&15-KETOPROSTAGLANDIN E2&&
|Common Name=&&15-keto Prostaglandin E_2&&7- [ 3 (R) -Hydroxy-2 (R) - (3-oxo-1 (E) -octenyl) -5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid&&
|Mass Spectra=DIMETHOXIME TMS ETHER METHYL ESTER ; m/z 494(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 479, 463, 404, 373, 321, 180 [[Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579|{{RelationTable/GetFirstAuthor|Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579}}]]
|Mass Spectra=DIMETHOXIME TMS ETHER METHYL ESTER ; m/z 494(M^+ ), 479, 463, 404, 373, 321, 180 [[Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579|{{RelationTable/GetFirstAuthor|Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579}}]]
|UV Spectra=METHYL ESTER ; <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> = 227nm (<FONT FACE="Symbol">e</FONT> ˜ 9000) [[Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579|{{RelationTable/GetFirstAuthor|Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579}}]]
|UV Spectra=METHYL ESTER ; lambda  ^{MeOH}_{max} = 227nm ( epsilon  &#8764; 9000) [[Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579|{{RelationTable/GetFirstAuthor|Reference:Morrison_AR:McLaughlin_L:Bloch_M:Needleman_P:,J. Biol. Chem.,1984,259,13579}}]]
|Source=15-Keto-prostaglandin E2 is the oxidized product of prostaglandin E2 by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-hydroxyl group [[Reference:Hansen_HS:,Prostaglandins,1976,12,647|{{RelationTable/GetFirstAuthor|Reference:Hansen_HS:,Prostaglandins,1976,12,647}}]].
|Chemical Synthesis=
|Metabolism=15-Keto-prostaglandin E2 is further metabolized by its  Delta 13-reduction,  beta -oxidation and  omega  oxidation. The ultimate metabolite is (7 alpha -hydroxy-5,11-diketotetranorprosta-1,16-dioic acid) and excreted in urine [[Reference:Hamberg_M:Samuelsson_B:,J. Biol. Chem.,1971,246,6713|{{RelationTable/GetFirstAuthor|Reference:Hamberg_M:Samuelsson_B:,J. Biol. Chem.,1971,246,6713}}]].
|Symbol=15-KETO-PGE2
|Biological Activity=It is well known that the biological activities of various prostaglandins are reduced upon their dehydrogenation at carbon-15 by the catalysis of 15-hydroxyprostaglandin dehydrogenase [[Reference:Anggard_E:,Acta Physiol. Scand.,1966,66,509|{{RelationTable/GetFirstAuthor|Reference:Anggard_E:,Acta Physiol. Scand.,1966,66,509}}]].
|Genetic Information=cDNA for placental 15-hydroxyprostaglandin dehydrogenase was cloned [[Reference:Ensor_CM:Tai_HH:,J. Lipid Mediat. Cell Signal.,1995,12,313|{{RelationTable/GetFirstAuthor|Reference:Ensor_CM:Tai_HH:,J. Lipid Mediat. Cell Signal.,1995,12,313}}]].
}}
}}
{{Lipid/Footer}}

Latest revision as of 08:30, 21 October 2010

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Upper classes: LB LBF



15-keto Prostaglandin E2
LBF20207PG24.png
Structural Information
7- [3R -Hydroxy-2R - (3-oxo-trans-1-octenyl) -5-oxocyclopentan-1R -yl] -cis-5-heptenoic acid
  • 15-keto Prostaglandin E2
  • 7- [ 3 (R) -Hydroxy-2 (R) - (3-oxo-1 (E) -octenyl) -5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
15-KETO-PGE2
Formula C20H30O5
Exact Mass 350.20932407
Average Mass 350.4492
SMILES C(CCC(=O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)[C@@H](CC1=O)O)CC
Physicochemical Information
15-Keto-prostaglandin E2 is the oxidized product of prostaglandin E2 by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-hydroxyl group Hansen_HS .
15-Keto-prostaglandin E2 is further metabolized by its Delta 13-reduction, beta -oxidation and omega oxidation. The ultimate metabolite is (7 alpha -hydroxy-5,11-diketotetranorprosta-1,16-dioic acid) and excreted in urine Hamberg_M et al..
It is well known that the biological activities of various prostaglandins are reduced upon their dehydrogenation at carbon-15 by the catalysis of 15-hydroxyprostaglandin dehydrogenase Anggard_E .
cDNA for placental 15-hydroxyprostaglandin dehydrogenase was cloned Ensor_CM et al..
Spectral Information
Mass Spectra DIMETHOXIME TMS ETHER METHYL ESTER ; m/z 494(M+), 479, 463, 404, 373, 321, 180 Morrison_AR et al.
UV Spectra METHYL ESTER ; λ MeOH
max
     = 227nm ( ε ∼ 9000) Morrison_AR et al.
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG24 See above. Anggard_E 1966
n.a. LBF20207PG24 See above. Ensor_CM et al. 1995
n.a. LBF20207PG24 See above. Hamberg_M et al. 1971
n.a. LBF20207PG24 See above. Hansen_HS 1976
n.a. LBF20207PG24 See above. Morrison_AR et al. 1984