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|LipidBank=XPR1001
|LipidBank=XPR1001
|LipidMaps=LMFA03010035
|LipidMaps=LMFA03010035
|SysName=7- [ 2 (R) - (3 (S) -Hydroxy-1 (E) -octenyl) -5-oxo-3-cyclopenten-1 (R) -yl ] -5 (Z) -heptenoic acid
|SysName=9-Oxo-15S-hydroxy- (cis-5,cis-10,trans-13) -prostatrienoic acid
|Common Name=&&PROSTAGLANDIN A_2&&7- [ 2 (R) - (3 (S) -Hydroxy-1 (E) -octenyl) -5-oxo-3-cyclopenten-1 (R) -yl ] -5 (Z) -heptenoic acid&&
|Common Name=&&Prostaglandin A_2&&7- [2R- (3S-Hydroxy-1-(E)-octenyl) -5-oxo-3-cyclopenten-1R-yl] -5-(Z) -heptenoic acid&&9-Oxo-15S-hydroxy- (5Z,10Z,13E) -prostatrienoic acid&&
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>20</sup>=+140°(C=1.15, CHLOROFORM) [[Reference:Corey_EJ:Moinet_G:,J. Am. Chem. Soc.,1973,95,6331|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Moinet_G:,J. Am. Chem. Soc.,1973,95,6331}}]]
|Optical=[ alpha ]X^{20}_D =+140°(C=1.15, CHLOROFORM) [[Reference:Corey_EJ:Moinet_G:,J. Am. Chem. Soc.,1973,95,6331|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Moinet_G:,J. Am. Chem. Soc.,1973,95,6331}}]]
|Solubility=ETHANOL, CHLOROFORM, METHANOL, DIETHYLETHER [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|Solubility=ETHANOL, CHLOROFORM, METHANOL, DIETHYLETHER [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|Mass Spectra=m/e 334(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 316, 190 [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|Mass Spectra=m/e 334(M^+ ), 316, 190 [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|UV Spectra=EtOH: 217 nm (<FONT FACE="Symbol">e</FONT> 9900) [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|UV Spectra=EtOH: 217 nm ( epsilon  9900) [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|IR Spectra=NUJOL : <FONT FACE="Symbol">n</FONT> 3400, 1705, 1580, 1255, 1115, 1070, 1015 cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|IR Spectra=NUJOL : nu  3400, 1705, 1580, 1255, 1115, 1070, 1015 cm^{-1} [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT> 7.57(dd, 1H, 10-CH), 6.2(dd, 1H, 11-CH), 5.6(m, 2H, 13,14-CH), 5.4 (m, 2H, 5,6-CH), 4.12(1H, m, 12-CH), 3.23(m, 1H), 0.89(t, 3H, 0-CH3) [[Reference:Schneider_WP:Bundy_GL:Lincoln_FH:Daniels_EG:Pike_JE:,J. Am. Chem. Soc.,1977,99,1222|{{RelationTable/GetFirstAuthor|Reference:Schneider_WP:Bundy_GL:Lincoln_FH:Daniels_EG:Pike_JE:,J. Am. Chem. Soc.,1977,99,1222}}]]. METHYL ESTER : <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR(CDCl3) 210.3, 174.0, 165.0, 135.2, 133.3, 131.0, 130.2, 126.7, 72.4, 52.1, 51.5, 49.6, 37.3, 33.5, 31.8, 27.4, 26.7, 25.1, 24.8, 22.6, 14.0 [[Reference:Cooper_GF:Fried_J:,Proc. Natl. Acad. Sci. U. S. A.,1973,70,1579|{{RelationTable/GetFirstAuthor|Reference:Cooper_GF:Fried_J:,Proc. Natl. Acad. Sci. U. S. A.,1973,70,1579}}]]
|NMR Spectra=^1 H-NMR(CDCl_3 ) : delta  7.57(dd, 1H, 10-CH), 6.2(dd, 1H, 11-CH), 5.6(m, 2H, 13,14-CH), 5.4 (m, 2H, 5,6-CH), 4.12(1H, m, 12-CH), 3.23(m, 1H), 0.89(t, 3H, 0-CH3) [[Reference:Schneider_WP:Bundy_GL:Lincoln_FH:Daniels_EG:Pike_JE:,J. Am. Chem. Soc.,1977,99,1222|{{RelationTable/GetFirstAuthor|Reference:Schneider_WP:Bundy_GL:Lincoln_FH:Daniels_EG:Pike_JE:,J. Am. Chem. Soc.,1977,99,1222}}]]. METHYL ESTER : ^{13}C-NMR(CDCl3) 210.3, 174.0, 165.0, 135.2, 133.3, 131.0, 130.2, 126.7, 72.4, 52.1, 51.5, 49.6, 37.3, 33.5, 31.8, 27.4, 26.7, 25.1, 24.8, 22.6, 14.0 [[Reference:Cooper_GF:Fried_J:,Proc. Natl. Acad. Sci. U. S. A.,1973,70,1579|{{RelationTable/GetFirstAuthor|Reference:Cooper_GF:Fried_J:,Proc. Natl. Acad. Sci. U. S. A.,1973,70,1579}}]]
|Source=Prostaglandin A2 was found in human semen in an amount of about 50 micrograms per ml as measured in combination with prostaglandins A1, B1 and B2 [[Reference:Bergstrom_S:,Science,1967,157,382|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:,Science,1967,157,382}}]].
|Chemical Synthesis=[[Reference:Corey_EJ:Moinet_G:,J. Am. Chem. Soc.,1973,95,6331|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Moinet_G:,J. Am. Chem. Soc.,1973,95,6331}}]] {{Image200|LBF20307PG01FT0001.gif}}
|Metabolism=Prostaglandin A2 is produced by non-enzymatic degradation of prostaglandin E2 [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]], and human serum has an enzymatic activity to convert prostaglandin E2 to A2 [[Reference:Polet_H:Levine_L:,J. Biol. Chem.,1975,250,351|{{RelationTable/GetFirstAuthor|Reference:Polet_H:Levine_L:,J. Biol. Chem.,1975,250,351}}]].
|Symbol=PGA2
|Biological Activity=Antitumor activity of prostaglandin A2 is known [[Reference:Fukushima_M:,Eicosanoids,1990,3,189|{{RelationTable/GetFirstAuthor|Reference:Fukushima_M:,Eicosanoids,1990,3,189}}]], and prostaglandin A2 rduces blood pressure [[Reference:Bergstrom_S:Carlson_LA:Weeks_JR:,Pharmacol. Rev.,1968,20,1|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:Carlson_LA:Weeks_JR:,Pharmacol. Rev.,1968,20,1}}]].
}}
}}


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Latest revision as of 20:53, 2 November 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR1001
LipidMaps LMFA03010035
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20307PG01
Prostaglandin A2
Structural Information
9-Oxo-15S-hydroxy- (cis-5,cis-10,trans-13) -prostatrienoic acid
  • Prostaglandin A2
  • 7- [2R- (3S-Hydroxy-1-(E)-octenyl) -5-oxo-3-cyclopenten-1R-yl] -5-(Z) -heptenoic acid
  • 9-Oxo-15S-hydroxy- (5Z,10Z,13E) -prostatrienoic acid
 PGA2
Formula C20H30O4
Exact Mass 334.21440944799997
Average Mass 334.4498
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)C=CC(=O)1)CC
Physicochemical Information
[ α ]X20
D   =+140°(C=1.15, CHLOROFORM) Corey_EJ et al.
ETHANOL, CHLOROFORM, METHANOL, DIETHYLETHER Pike_JE et al.
Prostaglandin A2 was found in human semen in an amount of about 50 micrograms per ml as measured in combination with prostaglandins A1, B1 and B2 Bergstrom_S .
Corey_EJ et al.

Prostaglandin A2 is produced by non-enzymatic degradation of prostaglandin E2 Pike_JE et al., and human serum has an enzymatic activity to convert prostaglandin E2 to A2 Polet_H et al..
Antitumor activity of prostaglandin A2 is known Fukushima_M , and prostaglandin A2 rduces blood pressure Bergstrom_S et al..
Spectral Information
Mass Spectra m/e 334(M+), 316, 190 Pike_JE et al.
UV Spectra EtOH: 217 nm ( ε 9900) Pike_JE et al.
IR Spectra NUJOL : ν 3400, 1705, 1580, 1255, 1115, 1070, 1015 cm-1 Pike_JE et al.
NMR Spectra 1H-NMR(CDCl3) : δ 7.57(dd, 1H, 10-CH), 6.2(dd, 1H, 11-CH), 5.6(m, 2H, 13,14-CH), 5.4 (m, 2H, 5,6-CH), 4.12(1H, m, 12-CH), 3.23(m, 1H), 0.89(t, 3H, 0-CH3) Schneider_WP et al.. METHYL ESTER : 13C-NMR(CDCl3) 210.3, 174.0, 165.0, 135.2, 133.3, 131.0, 130.2, 126.7, 72.4, 52.1, 51.5, 49.6, 37.3, 33.5, 31.8, 27.4, 26.7, 25.1, 24.8, 22.6, 14.0 Cooper_GF et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20307PG01 See above. Bergstrom_S 1967
n.a. LBF20307PG01 See above. Bergstrom_S et al. 1968
n.a. LBF20307PG01 See above. Cooper_GF et al. 1973
n.a. LBF20307PG01 See above. Corey_EJ et al. 1973
n.a. LBF20307PG01 See above. Fukushima_M 1990
n.a. LBF20307PG01 See above. Pike_JE et al. 1969
n.a. LBF20307PG01 See above. Polet_H et al. 1975
n.a. LBF20307PG01 See above. Schneider_WP et al. 1977


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