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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}


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|LipidBank=XPR1430
|LipidBank=XPR1430
|LipidMaps=LMFA03010012
|LipidMaps=LMFA03010012
|SysName=7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -5-oxocyclopentan-1 (R) -yl ] -6-oxoheptanoic acid
|SysName=7- [3R- Hydroxy- 2R- (3S-hydroxy-trans-1-octenyl) -5-oxocyclopentan-1R-yl] -oxoheptanoic acid
|Common Name=&&6-KETO-PROSTAGLANDIN E_1&&7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -5-oxocyclopentan-1 (R) -yl ] -6-oxoheptanoic acid&&
|Common Name=&&6-keto Prostaglandin E_1&&7- [3R- Hydroxy- 2R- (3S -hydroxy-1-(E) -octenyl) -5-oxocyclopentan-1R-yl] -oxoheptanoic acid&&
|Melting Point=65°C [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|Melting Point=65°C [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>20</sup>=-50°(C=1.55, METHANOL) [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|Optical=[ alpha ]X^{20}_D =-50°(C=1.55, METHANOL) [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|Solubility=METHANOL, CHLOROFORM [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|Solubility=METHANOL, CHLOROFORM [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|Mass Spectra=DIRECT EXPOSURE AMMONIA CI, POSITIVE : 386(M<SUP><FONT SIZE=-1>+</FONT></SUP>+18), 368(M+), 351, 350, 244, 136. NEGATIVE : 368(M<SUP><FONT SIZE=-1>+</FONT></SUP>) ,350, 338, 332 [[Reference:Cepa_SR:Hall_ER:Venton_DL:,Prostaglandins,1984,27,645|{{RelationTable/GetFirstAuthor|Reference:Cepa_SR:Hall_ER:Venton_DL:,Prostaglandins,1984,27,645}}]]
|Mass Spectra=DIRECT EXPOSURE AMMONIA CI, POSITIVE : 386(M^+ +18), 368(M+), 351, 350, 244, 136. NEGATIVE : 368(M^+ ) ,350, 338, 332 [[Reference:Cepa_SR:Hall_ER:Venton_DL:,Prostaglandins,1984,27,645|{{RelationTable/GetFirstAuthor|Reference:Cepa_SR:Hall_ER:Venton_DL:,Prostaglandins,1984,27,645}}]]
|IR Spectra=KBr: <FONT FACE="Symbol">n</FONT> 3400, 1740, 1720, 1710, 1245, 1160, 1075, 970 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|IR Spectra=KBr: nu  3400, 1740, 1720, 1710, 1245, 1160, 1075, 970 cm^{-1} [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT> 5.58(m, 2H, 13,14-CH), 4.09(m, 1H, 11-CH), 4.02(m, 1H, 15-CH), 2.7(2H, 7-CH), 2.69(IH, 10<FONT FACE="Symbol">b</FONT>-CH), 2.45-2.47(m, 3H, 5,8,12-CH), 2.29(1H, 10<FONT FACE="Symbol">a</FONT>-CH), 2.28(2H, 2-CH), 1.58 - 1.32(12H), 0.91(t, 3H, 20-CH<SUB><FONT SIZE=-1>3</FONT></SUB>) [[Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1982,60,2617|{{RelationTable/GetFirstAuthor|Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1982,60,2617}}]]. METHYL ESTER ; <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : 216.6, 208.4, 173.8, 138.0, 126.5, 72.3, 51.5, 44.6, 45.7, 42.4, 37.6, 33.8, 31.8, 25.2, 24.5, 23.4, 22.6, 14.0 [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|NMR Spectra=^1 H-NMR(CDCl_3 ) : delta  5.58(m, 2H, 13,14-CH), 4.09(m, 1H, 11-CH), 4.02(m, 1H, 15-CH), 2.7(2H, 7-CH), 2.69(IH, 10 beta -CH), 2.45-2.47(m, 3H, 5,8,12-CH), 2.29(1H, 10 alpha -CH), 2.28(2H, 2-CH), 1.58 - 1.32(12H), 0.91(t, 3H, 20-CH_3 ) [[Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1982,60,2617|{{RelationTable/GetFirstAuthor|Reference:Kotovych_G:Aarts_GHM:,Can. J. Chem.,1982,60,2617}}]]. METHYL ESTER ; ^{13}C-NMR(CDCl_3 ) : 216.6, 208.4, 173.8, 138.0, 126.5, 72.3, 51.5, 44.6, 45.7, 42.4, 37.6, 33.8, 31.8, 25.2, 24.5, 23.4, 22.6, 14.0 [[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]]
|Source=There were reports of prolonged biological activity of chemically unstable prostaglandin I2, which suggested a possible transformation of prostaglandin I2 to a more stable metabolite with potent bioactivity [[Reference:Wong_PY:Lee_WH:Chao_PH:Reiss_RF:McGiff_JC:,J. Biol. Chem.,1980,255,9021|{{RelationTable/GetFirstAuthor|Reference:Wong_PY:Lee_WH:Chao_PH:Reiss_RF:McGiff_JC:,J. Biol. Chem.,1980,255,9021}}]]. Further investigations led to the discovery of 6-keto-prostaglandin E1.
|Chemical Synthesis=[[Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813|{{RelationTable/GetFirstAuthor|Reference:Tanaka_T:Hazato_A:Bannai_K:Okamura_N:Sugiura_S:Manabe_K:Toru_T:Kurozumi_S:Suzuki_M:Kawagishi_T_et_al:,Tetrahedron,1987,43,813}}]] {{Image200|LBF20107PG02FT0001.gif}}
|Metabolism=A potential role of 9-hydroxyprostaglandin dehydrogenase was demonstrated in the transformation of prostaglandin I2 to 6-keto-prostaglandin E1 [[Reference:Wong_PY:Lee_WH:Chao_PH:Reiss_RF:McGiff_JC:,J. Biol. Chem.,1980,255,9021|{{RelationTable/GetFirstAuthor|Reference:Wong_PY:Lee_WH:Chao_PH:Reiss_RF:McGiff_JC:,J. Biol. Chem.,1980,255,9021}}]].
|Symbol=6-KETO-PGE1
|Biological Activity=6-Keto-prostaglandin E1 is a stable metabolite. The compound inhibits platelet aggregation with activity comparable or greater than prostaglandin D2 although less potent than prostaglandin I2. Its vasodilatory and hypotensive activities, bronchodilatory property, and inhibition of gastric acid secretion were reported [[Reference:Moore_PK:Griffiths_RJ:,Prostaglandins,1983,26,509|{{RelationTable/GetFirstAuthor|Reference:Moore_PK:Griffiths_RJ:,Prostaglandins,1983,26,509}}]].
}}
}}
{{Lipid/Footer}}

Latest revision as of 08:00, 21 October 2010

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Upper classes: LB LBF



6-keto Prostaglandin E1
LBF20107PG02.png
Structural Information
7- [3R- Hydroxy- 2R- (3S-hydroxy-trans-1-octenyl) -5-oxocyclopentan-1R-yl] -oxoheptanoic acid
  • 6-keto Prostaglandin E1
  • 7- [3R- Hydroxy- 2R- (3S -hydroxy-1-(E) -octenyl) -5-oxocyclopentan-1R-yl] -oxoheptanoic acid
6-KETO-PGE1
Formula C20H32O6
Exact Mass 368.219888756
Average Mass 368.46448
SMILES C(CC[C@@H](O)C=C[C@H]([C@@H](CC(=O)CCCCC(O)=O)1)[C@@H](CC1=O)O)CC
Physicochemical Information
65°C Tanaka_T et al.
[ α ]X20
D
   =-50°(C=1.55, METHANOL) TanakaTet al.
METHANOL, CHLOROFORM TanakaTet al.
There were reports of prolonged biological activity of chemically unstable prostaglandin I2, which suggested a possible transformation of prostaglandin I2 to a more stable metabolite with potent bioactivity Wong_PY et al.. Further investigations led to the discovery of 6-keto-prostaglandin E1.
Tanaka_T et al.
LBF20107PG02FT0001.gif
A potential role of 9-hydroxyprostaglandin dehydrogenase was demonstrated in the transformation of prostaglandin I2 to 6-keto-prostaglandin E1 Wong_PY et al..
6-Keto-prostaglandin E1 is a stable metabolite. The compound inhibits platelet aggregation with activity comparable or greater than prostaglandin D2 although less potent than prostaglandin I2. Its vasodilatory and hypotensive activities, bronchodilatory property, and inhibition of gastric acid secretion were reported Moore_PK et al..
Spectral Information
Mass Spectra DIRECT EXPOSURE AMMONIA CI, POSITIVE : 386(M++18), 368(M+), 351, 350, 244, 136. NEGATIVE : 368(M+) ,350, 338, 332 Cepa_SR et al.
UV Spectra
IR Spectra KBr: ν 3400, 1740, 1720, 1710, 1245, 1160, 1075, 970 cm-1 TanakaTet al.
NMR Spectra 1H-NMR(CDCl3) : δ 5.58(m, 2H, 13,14-CH), 4.09(m, 1H, 11-CH), 4.02(m, 1H, 15-CH), 2.7(2H, 7-CH), 2.69(IH, 10 β -CH), 2.45-2.47(m, 3H, 5,8,12-CH), 2.29(1H, 10 α -CH), 2.28(2H, 2-CH), 1.58 - 1.32(12H), 0.91(t, 3H, 20-CH3) KotovychGet al.. METHYL ESTER ; 13C-NMR(CDCl3) : 216.6, 208.4, 173.8, 138.0, 126.5, 72.3, 51.5, 44.6, 45.7, 42.4, 37.6, 33.8, 31.8, 25.2, 24.5, 23.4, 22.6, 14.0 TanakaTet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20107PG02 See above. Cepa_SR et al. 1984
n.a. LBF20107PG02 See above. Kotovych_G et al. 1982
n.a. LBF20107PG02 See above. Moore_PK et al. 1983
n.a. LBF20107PG02 See above. Tanaka_T et al. 1987
n.a. LBF20107PG02 See above. Wong_PY et al. 1980