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|LipidBank=XPR1402
|LipidBank=XPR1402
|LipidMaps=LMFA03010135
|LipidMaps=LMFA03010135
|SysName=7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxyocta-1 (E) ,5 (Z) -dienyl) -5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid / (5Z,8R,11R,12R,13E,15S,17Z) -11,15-Dihydroxy-9-oxo-5,13,17-prostatrienoic acid
|SysName=7- [3R-Hydroxy-2R- (3S-hydroxyocta- (trans-1,cis-5) -dienyl) -5-oxocyclopentan-1R-yl ] -cis-5-heptenoic acid
|Common Name=&&PROSTAGLANDIN E_3&&7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxyocta-1 (E) ,5 (Z) -dienyl) -5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid&&(5Z,8R,11R,12R,13E,15S,17Z) -11,15-Dihydroxy-9-oxo-5,13,17-prostatrienoic acid&&
|Common Name=&&Prostaglandin E_3&&(5Z,8R,11R,12R,13E,15S,17Z) -11,15-Dihydroxy-9-oxo-5,13,17-prostatrienoic acid&&7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxyocta-1 (E) ,5 (Z) -dienyl) -5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid&&
|Melting Point=84.5-85.5°C  
|Melting Point=84.5-85.5°C [[Reference:Okamoto K:Kobayashi_Y:Sato_F:,Tetrahedron Lett.,1989,30,4379|{{RelationTable/GetFirstAuthor|Reference:Okamoto K:Kobayashi_Y:Sato_F:,Tetrahedron Lett.,1989,30,4379}}]]
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>24</sup>=-48.9°(C=1.2, TETRAHYDROFURAN) [[Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490}}]]
|Optical=[ alpha ]^{24}_D =-48.9°(C=1.2, TETRAHYDROFURAN) [[Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490}}]]
|Solubility=TETRAHYDROFURAN [[Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490}}]]
|Solubility=TETRAHYDROFURAN [[Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490}}]]
|Mass Spectra=METHYL ESTER ; m/e 346(M-18), 328(M-18x2), 315, 297, 277, 259, 188 [[Reference:Bergstroem_S:Dressler_F:Ryhage_R:Samuelsson_B:Sjoevall_J:,Ark. Kemi.,1962,19,563|{{RelationTable/GetFirstAuthor|Reference:Bergstroem_S:Dressler_F:Ryhage_R:Samuelsson_B:Sjoevall_J:,Ark. Kemi.,1962,19,563}}]]
|Mass Spectra=METHYL ESTER ; m/e 346(M-18), 328(M-18x2), 315, 297, 277, 259, 188 [[Reference:Bergstroem_S:Dressler_F:Ryhage_R:Samuelsson_B:Sjoevall_J:,Ark. Kemi.,1962,19,563|{{RelationTable/GetFirstAuthor|Reference:Bergstroem_S:Dressler_F:Ryhage_R:Samuelsson_B:Sjoevall_J:,Ark. Kemi.,1962,19,563}}]]
|NMR Spectra=METHYL ESTER ; <SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT> 5.8-5.5(m, 2H,13, 14-CH), 5.5-5.2(m, 4H, 5,6,17,18-CH), 4.4-3.8(m, 2H, 11,15-CH), 0.95(t, 3H, 20-CH) [[Reference:Samuelsson_B:,J. Am. Chem. Soc.,1963,85,1878|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:,J. Am. Chem. Soc.,1963,85,1878}}]]
|NMR Spectra=METHYL ESTER ; ^1 H-NMR(CDCl_3 ) : delta  5.8-5.5(m, 2H,13, 14-CH), 5.5-5.2(m, 4H, 5,6,17,18-CH), 4.4-3.8(m, 2H, 11,15-CH), 0.95(t, 3H, 20-CH) [[Reference:Samuelsson_B:,J. Am. Chem. Soc.,1963,85,1878|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:,J. Am. Chem. Soc.,1963,85,1878}}]]
|Source=Prostaglandin E3 is contained in human seminal plasma in an amount of 5.5 micrograms/ml [[Reference:Bergstrom_S:,Science,1967,157,382|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:,Science,1967,157,382}}]], and also found in ovine seminal vesicle and plasma [[Reference:Speroff_L:Ramwell_PW:,Am. J. Obstet. Gynecol.,1970,107,1111|{{RelationTable/GetFirstAuthor|Reference:Speroff_L:Ramwell_PW:,Am. J. Obstet. Gynecol.,1970,107,1111}}]].
|Chemical Synthesis=[[Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Shirahama_H:Yamamoto_H:Terashima_S:Venkateswarlu_A:Schaaf_TK:,J. Am. Chem. Soc.,1971,93,1490}}]] {{Image200|LBF20303PG03FT0001.gif}}
|Metabolism=
|Symbol=PGE3
|Biological Activity=As presented in Table 1 of reference [[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 E3 is 1/10-1/2 as active as prostaglandin E2.
}}
}}


{{Lipid/Footer}}
{{Lipid/Footer}}

Latest revision as of 17:55, 21 October 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR1402
LipidMaps LMFA03010135
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20303PG03
Prostaglandin E3
Structural Information
7- [3R-Hydroxy-2R- (3S-hydroxyocta- (trans-1,cis-5) -dienyl) -5-oxocyclopentan-1R-yl ] -cis-5-heptenoic acid
  • Prostaglandin E3
  • (5Z,8R,11R,12R,13E,15S,17Z) -11,15-Dihydroxy-9-oxo-5,13,17-prostatrienoic acid
  • 7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxyocta-1 (E) ,5 (Z) -dienyl) -5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
 PGE3
Formula C20H30O5
Exact Mass 350.20932407
Average Mass 350.4492
SMILES C(=CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)[C@@H](CC1=O)O)CC
Physicochemical Information
84.5-85.5°C Okamoto K et al.
[ α ]24
D   =-48.9°(C=1.2, TETRAHYDROFURAN) Corey_EJ et al.
TETRAHYDROFURAN Corey_EJ et al.
Prostaglandin E3 is contained in human seminal plasma in an amount of 5.5 micrograms/ml Bergstrom_S , and also found in ovine seminal vesicle and plasma Speroff_L et al..
Corey_EJ et al.

As presented in Table 1 of reference Bergstrom_S et al., prostaglandin E3 is 1/10-1/2 as active as prostaglandin E2.
Spectral Information
Mass Spectra METHYL ESTER ; m/e 346(M-18), 328(M-18x2), 315, 297, 277, 259, 188 BergstroemSet al.
UV Spectra
IR Spectra
NMR Spectra METHYL ESTER ; 1H-NMR(CDCl3) : δ 5.8-5.5(m, 2H,13, 14-CH), 5.5-5.2(m, 4H, 5,6,17,18-CH), 4.4-3.8(m, 2H, 11,15-CH), 0.95(t, 3H, 20-CH) SamuelssonB
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20303PG03 See above. Bergstroem_S et al. 1962
n.a. LBF20303PG03 See above. Bergstrom_S 1967
n.a. LBF20303PG03 See above. Bergstrom_S et al. 1968
n.a. LBF20303PG03 See above. Corey_EJ et al. 1971
n.a. LBF20303PG03 See above. Okamoto_K et al. 1989
n.a. LBF20303PG03 See above. Samuelsson_B 1963
n.a. LBF20303PG03 See above. Speroff_L et al. 1970


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