LBF20107PG18: Difference between revisions

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Upper classes: LB LBF

6-keto Prostaglandin F_1α

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) Tanaka_Tet al.

	DIETHYL ETHER Pace-Asciak_CMETHANOL, ACETONE, ETHYL ACETATE Tanaka_Tet 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.
	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 Tanaka_Tet 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 Tanaka_Tet 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) Tanaka_Tet al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
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

@@ Line 6: / Line 6: @@
 |LipidBank=XPR1811
 |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}}]]
-|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|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}}]].
 }}
 {{Lipid/Footer}}

IDs and Links
LipidBank	XPR1811
LipidMaps	LMFA03010001
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}

mol	LBF20107PG18

LBF20107PG18: Difference between revisions

Latest revision as of 17:14, 21 October 2010

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