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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
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|LipidBank=XPR1501
|LipidBank=XPR1501
|LipidMaps=LMFA03010002
|LipidMaps=LMFA03010002
|SysName=7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenylcyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
|SysName=7- [ (3R,5S) -Dihydroxy-2R - (3S -hydroxy-trans-1-octenyl) cyclopentan-1R -yl] -cis-5-heptenoic acid
|Common Name=&&PROSTAGLANDIN F_2alpha&&
|Common Name=&&Prostaglandin F_2 alpha&&7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid&&
|Melting Point=25-35°C [[Reference:Bundy_GL:Schneider_WP:Lincoln_FH:Pike_JE:,J. Am. Chem. Soc.,1972,94,2123|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Schneider_WP:Lincoln_FH:Pike_JE:,J. Am. Chem. Soc.,1972,94,2123}}]]
|Melting Point=25-35°C [[Reference:Bundy_GL:Schneider_WP:Lincoln_FH:Pike_JE:,J. Am. Chem. Soc.,1972,94,2123|{{RelationTable/GetFirstAuthor|Reference:Bundy_GL:Schneider_WP:Lincoln_FH:Pike_JE:,J. Am. Chem. Soc.,1972,94,2123}}]]
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>25</sup>=23.8 °(C=1,THF) [[Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397}}]]
|Optical=[ alpha ]^{25}_D =23.8 °(C=1,THF) [[Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397}}]]
|Solubility= ETHYL ACETATE, ACETONE, 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}}]]. STABILITIES: to be stable under neutral and basic conditions [[Reference:Karim_SM:Devlin_J:Hillier_K:,Eur. J. Pharmacol.,1968,4,416|{{RelationTable/GetFirstAuthor|Reference:Karim_SM:Devlin_J:Hillier_K:,Eur. J. Pharmacol.,1968,4,416}}]]
|Solubility= ETHYL ACETATE, ACETONE, 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}}]]. STABILITIES: to be stable under neutral and basic conditions [[Reference:Karim_SM:Devlin_J:Hillier_K:,Eur. J. Pharmacol.,1968,4,416|{{RelationTable/GetFirstAuthor|Reference:Karim_SM:Devlin_J:Hillier_K:,Eur. J. Pharmacol.,1968,4,416}}]]
|Mass Spectra=354(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 [[Reference:Horvath_G:,Biomed. Mass Spectrom.,1976,3,127|{{RelationTable/GetFirstAuthor|Reference:Horvath_G:,Biomed. Mass Spectrom.,1976,3,127}}]]
|Mass Spectra=354(M^+ ), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 [[Reference:Horvath_G:,Biomed. Mass Spectrom.,1976,3,127|{{RelationTable/GetFirstAuthor|Reference:Horvath_G:,Biomed. Mass Spectrom.,1976,3,127}}]]
|IR Spectra=NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm<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=NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm^{-1} [[Reference:Pike_JE:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:PikeJ_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(d<SUB><FONT SIZE=-1>6</FONT></SUB>-ACETONE) : <FONT FACE="Symbol">d</FONT> 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) [[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}}]]. <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 [[Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515|{{RelationTable/GetFirstAuthor|Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515}}]]
|NMR Spectra=^1 H-NMR(d_6 -ACETONE) : delta  5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) [[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}}]]. ^{13}C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 [[Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515|{{RelationTable/GetFirstAuthor|Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515}}]]
|Source=Prostaglandin F2 alpha  was found to be accummulating in human semen in an amount of about 2 microgram per ml [[Reference:Bergstrom_S:,Science,1967,157,382|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:,Science,1967,157,382}}]]. In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2 alpha .
|Chemical Synthesis=[[Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397}}]] {{Image200|LBF20207PG25FT0001.gif}}
|Metabolism=Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2 alpha . The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11 beta -prostaglandin F2 [[Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257|{{RelationTable/GetFirstAuthor|Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257}}]].
|Symbol=PGF2&alpha;
|Biological Activity=Prostaglandin F2 alpha  exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction [[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}}]]. Prostaglandin F2 alpha  is a ligand to a receptor (FP) present in the cell membrane [[Reference:Negishi_M:Sugimoto_Y:Ichikawa_A:,Biochim. Biophys. Acta,1995,1259,109|{{RelationTable/GetFirstAuthor|Reference:Negishi_M:Sugimoto_Y:Ichikawa_A:,Biochim. Biophys. Acta,1995,1259,109}}]].
|Genetic Information=cDNA for prostaglandin F synthase was cloned from bovine lung [[Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257|{{RelationTable/GetFirstAuthor|Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257}}]]. cDNA for prostaglandin F2 alpha  receptor (FP) was cloned, and its 7ptransmembrane structure was reported [[Reference:Negishi_M:Sugimoto_Y:Ichikawa_A:,Biochim. Biophys. Acta,1995,1259,109|{{RelationTable/GetFirstAuthor|Reference:Negishi_M:Sugimoto_Y:Ichikawa_A:,Biochim. Biophys. Acta,1995,1259,109}}]].
}}
 
{{MassbankSpectra|
UT000352
UT000353
UT000354
UT000355
UT000356
UT000357
UT000358
UT000359
UT000360
}}
}}
{{Lipid/Footer}}

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



IDs and Links
LipidBank XPR1501
LipidMaps LMFA03010002
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20207PG25
Prostaglandin F2α
LBF20207PG25.png
Structural Information
7- [ (3R,5S) -Dihydroxy-2R - (3S -hydroxy-trans-1-octenyl) cyclopentan-1R -yl] -cis-5-heptenoic acid
  • Prostaglandin F2α
  • 7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
 PGF2α
Formula C20H34O5
Exact Mass 354.240624198
Average Mass 354.48096000000004
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)[C@@H](C[C@@H]1O)O)CC
Physicochemical Information
25-35°C Bundy_GL et al.
[ α ]25
D   =23.8 °(C=1,THF) Corey_EJ et al.
ETHYL ACETATE, ACETONE, DIETHYLETHER Pike_JE et al.. STABILITIES: to be stable under neutral and basic conditions Karim_SM et al.
Prostaglandin F2 alpha was found to be accummulating in human semen in an amount of about 2 microgram per ml Bergstrom_S . In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2 alpha .
Corey_EJ et al.
LBF20207PG25FT0001.gif
 Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2 alpha . The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11 beta -prostaglandin F2 Urade_Y et al..
Prostaglandin F2 alpha exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction Bergstrom_S et al.. Prostaglandin F2 alpha is a ligand to a receptor (FP) present in the cell membrane Negishi_M et al..
cDNA for prostaglandin F synthase was cloned from bovine lung Urade_Y et al.. cDNA for prostaglandin F2 alpha receptor (FP) was cloned, and its 7ptransmembrane structure was reported Negishi_M et al..
Spectral Information
Mass Spectra 354(M+), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 HorvathG
UV Spectra
IR Spectra NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm-1 PikeJEet al.
NMR Spectra 1H-NMR(d6-ACETONE) : δ 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) Pike_JE et al.. 13C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 LukacsGet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG25 See above. Bergstrom_S 1967
n.a. LBF20207PG25 See above. Bergstrom_S et al. 1968
n.a. LBF20207PG25 See above. Bundy_GL et al. 1972
n.a. LBF20207PG25 See above. Corey_EJ et al. 1970
n.a. LBF20207PG25 See above. Horvath_G 1976
n.a. LBF20207PG25 See above. Karim_SM et al. 1968
n.a. LBF20207PG25 See above. Lukacs_G et al. 1973
n.a. LBF20207PG25 See above. Negishi_M et al. 1995
n.a. LBF20207PG25 See above. Pike_JE et al. 1969
n.a. LBF20207PG25 See above. Urade_Y et al. 1995



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