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|LipidBank=XPR1811
|LipidBank=XPR1811
|LipidMaps=LMFA03010001
|LipidMaps=LMFA03010001
|SysName=7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -6-oxoheptanoic acid
|SysName=7- [ (3R,5S) -Dihydroxy- 2R- (3S-hydroxy-trans-1-octenyl) cyclopentan-1R -yl ] -6-oxoheptanoic acid
|Common Name=&&6-KETOPROSTAGLANDIN F_1alpha&&7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -6-oxoheptanoic acid&&
|Common Name=&&6-keto Prostaglandin F_1alpha&&7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -6-oxoheptanoic acid &&
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>21</sup>= -9.6° (C=1.04 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 ]^{21}_D = -9.6° (C=1.04 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=DIETHYL ETHER[[Reference:Pace-Asciak_C:,J. Am. Chem. Soc.,1976,98,2348|{{RelationTable/GetFirstAuthor|Reference:Pace-Asciak_C:,J. Am. Chem. Soc.,1976,98,2348}}]]METHANOL, ACETONE, ETHYL ACETATE [[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=DIETHYL ETHER[[Reference:Pace-Asciak_C:,J. Am. Chem. Soc.,1976,98,2348|{{RelationTable/GetFirstAuthor|Reference:Pace-Asciak_C:,J. Am. Chem. Soc.,1976,98,2348}}]]METHANOL, ACETONE, ETHYL ACETATE [[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=METHYL ESTER ; 366(M<SUP><FONT SIZE=-1>+</FONT></SUP>-18), 348, 335, 330, 323, 319, 279, 265, 223, 196, 195, 164, 143, 121, 111, 99, 95, 71 [[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}}]]. DIRECT EXPOSURE AMMONIA CI POSITIVE : 370, 353, 244, 163, 153, 136. NEGATIVE : 368, 351, 334, 316, 225, 219, 166, 135, 127 [[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=METHYL ESTER ; 366(M^+ -18), 348, 335, 330, 323, 319, 279, 265, 223, 196, 195, 164, 143, 121, 111, 99, 95, 71 [[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}}]]. DIRECT EXPOSURE AMMONIA CI POSITIVE : 370, 353, 244, 163, 153, 136. NEGATIVE : 368, 351, 334, 316, 225, 219, 166, 135, 127 [[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=NEAT: <FONT FACE="Symbol">n</FONT> 3400, 1715, 1245, 1045, 975, 915, 875, 845, 800, 730 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=NEAT: nu  3400, 1715, 1245, 1045, 975, 915, 875, 845, 800, 730 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(ACETONE-D<SUB><FONT SIZE=-1>6</FONT></SUB>) : <FONT FACE="Symbol">d</FONT> 6.1-5.4(bs, 4H), 5.5-5.2(m, 2H), 4.7-3.5(m, 3H), 2.5-1.1 (m, 22H), 0.86(t, 3H) [[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(ACETONE-D_6 ) : delta  6.1-5.4(bs, 4H), 5.5-5.2(m, 2H), 4.7-3.5(m, 3H), 2.5-1.1 (m, 22H), 0.86(t, 3H) [[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=When prostaglandin I2 is produced in animal tissues, it is unstable in aqueous solution, especially at acidic pH, and readily decomposed to 6-keto-prostaglandin F1<FONT FACE="Symbol">a</FONT> [[Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293|{{RelationTable/GetFirstAuthor|Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293}}]];>. Therefore, 6-keto-prostaglandin F1<FONT FACE="Symbol">a</FONT> is detected where prostaglandin I2 is produced.
|Source=When prostaglandin I2 is produced in animal tissues, it is unstable in aqueous solution, especially at acidic pH, and readily decomposed to 6-keto-prostaglandin F1 alpha  [[Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293|{{RelationTable/GetFirstAuthor|Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293}}]]. Therefore, 6-keto-prostaglandin F1 alpha  is detected where prostaglandin I2 is produced.
|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|XPR1811FT0001.gif}}
|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|LBF20107PG18FT0001.gif}}
|Metabolism=6-Keto-prostaglandin F1<FONT FACE="Symbol">a</FONT> is subjected to <FONT FACE="Symbol">b</FONT>-oxidation, and converted to 2,3-dinor-6-keto-prostaglandin F1<FONT FACE="Symbol">a</FONT> which appears in urine as a major metabolite [[Reference:Needleman_P:Turk_J:Jakschik_BA:Morrison_AR:Lefkowith_JB:,Annu. Rev. Biochem.,1986,55,69|{{RelationTable/GetFirstAuthor|Reference:Needleman_P:Turk_J:Jakschik_BA:Morrison_AR:Lefkowith_JB:,Annu. Rev. Biochem.,1986,55,69}}]];>.
|Metabolism=6-Keto-prostaglandin F1 alpha  is subjected to beta -oxidation, and converted to 2,3-dinor-6-keto-prostaglandin F1 alpha  which appears in urine as a major metabolite [[Reference:Needleman_P:Turk_J:Jakschik_BA:Morrison_AR:Lefkowith_JB:,Annu. Rev. Biochem.,1986,55,69|{{RelationTable/GetFirstAuthor|Reference:Needleman_P:Turk_J:Jakschik_BA:Morrison_AR:Lefkowith_JB:,Annu. Rev. Biochem.,1986,55,69}}]].
|Symbol=6-KETO-PGF1&alpha;  
|Biological Activity=Degradation of prostaglandin I2 to 6-keto-prostaglandin F1 alpha  brings about the loss of biological activities. For example, the hypotensive effect of prostaglandin I2 is at least 100 times mor active than 6-keto-prostaglandin F1 alpha  [[Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293|{{RelationTable/GetFirstAuthor|Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293}}]].
}}
}}


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Latest revision as of 08:14, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR1811
LipidMaps LMFA03010001
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20107PG18
6-keto Prostaglandin F_1α
LBF20107PG18.png
Structural Information
7- [ (3R,5S) -Dihydroxy- 2R- (3S-hydroxy-trans-1-octenyl) cyclopentan-1R -yl ] -6-oxoheptanoic acid
  • 6-keto Prostaglandin F_1α
  • 7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -6-oxoheptanoic acid
 6-KETO-PGF1α
Formula C20H34O6
Exact Mass 370.23553882
Average Mass 370.48036
SMILES C(CC[C@@H](O)C=C[C@H]([C@@H](CC(=O)CCCCC(O)=O)1)[C@@H](C[C@@H]1O)O)CC
Physicochemical Information
[ α ]21
D   = -9.6° (C=1.04 METHANOL) TanakaTet al.
DIETHYL ETHER Pace-AsciakCMETHANOL, ACETONE, ETHYL ACETATE TanakaTet al.
When prostaglandin I2 is produced in animal tissues, it is unstable in aqueous solution, especially at acidic pH, and readily decomposed to 6-keto-prostaglandin F1 alpha Moncada_S et al.. Therefore, 6-keto-prostaglandin F1 alpha is detected where prostaglandin I2 is produced.
Tanaka_T et al.
LBF20107PG18FT0001.gif
 6-Keto-prostaglandin F1 alpha is subjected to beta -oxidation, and converted to 2,3-dinor-6-keto-prostaglandin F1 alpha which appears in urine as a major metabolite Needleman_P et al..
Degradation of prostaglandin I2 to 6-keto-prostaglandin F1 alpha brings about the loss of biological activities. For example, the hypotensive effect of prostaglandin I2 is at least 100 times mor active than 6-keto-prostaglandin F1 alpha Moncada_S et al..
Spectral Information
Mass Spectra METHYL ESTER ; 366(M+-18), 348, 335, 330, 323, 319, 279, 265, 223, 196, 195, 164, 143, 121, 111, 99, 95, 71 TanakaTet al.. DIRECT EXPOSURE AMMONIA CI POSITIVE : 370, 353, 244, 163, 153, 136. NEGATIVE : 368, 351, 334, 316, 225, 219, 166, 135, 127 Cepa_SR et al.
UV Spectra
IR Spectra NEAT: ν 3400, 1715, 1245, 1045, 975, 915, 875, 845, 800, 730 cm-1 TanakaTet al.
NMR Spectra 1H-NMR(ACETONE-D6) : δ 6.1-5.4(bs, 4H), 5.5-5.2(m, 2H), 4.7-3.5(m, 3H), 2.5-1.1 (m, 22H), 0.86(t, 3H) TanakaTet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20107PG18 See above. Cepa_SR et al. 1984
n.a. LBF20107PG18 See above. Moncada_S et al. 1978
n.a. LBF20107PG18 See above. Needleman_P et al. 1986
n.a. LBF20107PG18 See above. Pace-Asciak_C 1976
n.a. LBF20107PG18 See above. Tanaka_T et al. 1987


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