LBF20207PG51: Difference between revisions
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|IR Spectra=METHYL ESTER ; LIQUID MELT <FONT FACE="Symbol">n</FONT> 3370, 1740, 1695cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Johnson_RA:Lincoln_FH:Nidy_EG:Schneider_WP:Thompson_JL:Axen_U:,J. Am. Chem. Soc.,1978,100,7690|{{RelationTable/GetFirstAuthor|Reference:Johnson_RA:Lincoln_FH:Nidy_EG:Schneider_WP:Thompson_JL:Axen_U:,J. Am. Chem. Soc.,1978,100,7690}}]]
|IR Spectra=METHYL ESTER ; LIQUID MELT <FONT FACE="Symbol">n</FONT> 3370, 1740, 1695cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Johnson_RA:Lincoln_FH:Nidy_EG:Schneider_WP:Thompson_JL:Axen_U:,J. Am. Chem. Soc.,1978,100,7690|{{RelationTable/GetFirstAuthor|Reference:Johnson_RA:Lincoln_FH:Nidy_EG:Schneider_WP:Thompson_JL:Axen_U:,J. Am. Chem. Soc.,1978,100,7690}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>-H-NMR(D<SUB><FONT SIZE=-1>2</FONT></SUB>O, GLYCINE BUFFER, pH10.4) : <FONT FACE="Symbol">d</FONT> 5.60(m, 2H, 13,14-CH), 4.66(m, 1H, 9-CH), 4.39(t, 1H, 5-CH), 4.15(q, 1H, 15-CH), 3.97(q, 1H, 11-CH), 2.20(t, 2H, 2-CH<SUB><FONT SIZE=-1>2</FONT></SUB>) [[Reference:Kotovych_G:Aarts_GHM:Takashima_TT:Bigam_G:,Can. J. Chem.,1980,58,974|{{RelationTable/GetFirstAuthor|Reference:Kotovych_G:Aarts_GHM:Takashima_TT:Bigam_G:,Can. J. Chem.,1980,58,974}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>-H-NMR(D<SUB><FONT SIZE=-1>2</FONT></SUB>O, GLYCINE BUFFER, pH10.4) : <FONT FACE="Symbol">d</FONT> 5.60(m, 2H, 13,14-CH), 4.66(m, 1H, 9-CH), 4.39(t, 1H, 5-CH), 4.15(q, 1H, 15-CH), 3.97(q, 1H, 11-CH), 2.20(t, 2H, 2-CH<SUB><FONT SIZE=-1>2</FONT></SUB>) [[Reference:Kotovych_G:Aarts_GHM:Takashima_TT:Bigam_G:,Can. J. Chem.,1980,58,974|{{RelationTable/GetFirstAuthor|Reference:Kotovych_G:Aarts_GHM:Takashima_TT:Bigam_G:,Can. J. Chem.,1980,58,974}}]]
|Source=In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin I2. Prostaglandin I2 is produced in blood vessels, lung and other tissues [[Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293|{{RelationTable/GetFirstAuthor|Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293}}]];>.
|Chemical Synthesis=[[Reference:Johnson_RA:Lincoln_FH:Nidy_EG:Schneider_WP:Thompson_JL:Axen_U:,J. Am. Chem. Soc.,1978,100,7690|{{RelationTable/GetFirstAuthor|Reference:Johnson_RA:Lincoln_FH:Nidy_EG:Schneider_WP:Thompson_JL:Axen_U:,J. Am. Chem. Soc.,1978,100,7690}}]];> {{Image200|XPR1801FT0001.gif}}
|Metabolism=Prostaaglandin I2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2 by the catalysis of prostaglandin I synthaase [[Reference:Tanabe_T:Ullrich_V:,J. Lipid Mediat. Cell Signal.,1995,12,243|{{RelationTable/GetFirstAuthor|Reference:Tanabe_T:Ullrich_V:,J. Lipid Mediat. Cell Signal.,1995,12,243}}]];>. Prostaglandin I2 is unstable and decomposes readily to 6-keto-prostaglandin F2<FONT FACE="Symbol">a</FONT>. Its 2,3-dinor derivative is a major urinary 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}}]];>.
}}
}}


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Revision as of 22:00, 24 November 2009

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Upper classes: LB LBF



IDs and Links
LipidBank XPR1801
LipidMaps LMFA03010087
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20207PG51
PROSTAGLANDIN I2
LBF20207PG51.png
Structural Information
5 (Z) - [ 7 (R) -Hydroxy-6 (R) - (3 (S) -hydroxyocten-1 (E) -yl) -1 (S) ,5 (R) -2-oxabicyclo [ 3.3.0 ] oct-3-ylidenpentanoic acid
  • PROSTAGLANDIN I2
  • 5 (Z) - [ 7 (R) -Hydroxy-6 (R) - (3 (S) -hydroxyocten-1 (E) -yl) -1 (S) ,5 (R) -2-oxabicyclo [ 3.3.0 ] oct-3-ylidenpentanoic acid
Formula C20H32O5
Exact Mass 352.224974134
Average Mass 352.46508
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]12)[C@H](O)C[C@H](OC(C2)=CCCCC(O)=O)1)CC
Physicochemical Information
In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin I2. Prostaglandin I2 is produced in blood vessels, lung and other tissues Moncada_S et al.;>.
Johnson_RA et al.;>
File:XPR1801FT0001.gif
 Prostaaglandin I2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2 by the catalysis of prostaglandin I synthaase Tanabe_T et al.;>. Prostaglandin I2 is unstable and decomposes readily to 6-keto-prostaglandin F2a. Its 2,3-dinor derivative is a major urinary metabolite Needleman_P et al.;>.
Spectral Information
Mass Spectra 11,15-BIS(TRIMETHYLSILYL) ETHER METHYL ESTER ; 495(M+-CH3), 479, 439, 423, 349, 327, 323, 315, 313, 199, 173 Johnson_RA et al.
UV Spectra
IR Spectra METHYL ESTER ; LIQUID MELT n 3370, 1740, 1695cm-1 Johnson_RA et al.
NMR Spectra 1-H-NMR(D2O, GLYCINE BUFFER, pH10.4) : d 5.60(m, 2H, 13,14-CH), 4.66(m, 1H, 9-CH), 4.39(t, 1H, 5-CH), 4.15(q, 1H, 15-CH), 3.97(q, 1H, 11-CH), 2.20(t, 2H, 2-CH2) KotovychGet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG51 See above. Johnson_RA et al. 1978
n.a. LBF20207PG51 See above. Kotovych_G et al. 1980
n.a. LBF20207PG51 See above. Moncada_S et al. 1978
n.a. LBF20207PG51 See above. Needleman_P et al. 1986
n.a. LBF20207PG51 See above. Negishi_M et al. 1995
n.a. LBF20207PG51 See above. Negishi_M et al. 1995
n.a. LBF20207PG51 See above. Pace-Asciak_CR et al. 1983
n.a. LBF20207PG51 See above. Tanabe_T et al. 1995
n.a. LBF20207PG51 See above. Yokoyama_C et al. 1996


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