LBF20303PG03: Difference between revisions

Revision as of 01:14, 10 June 2010

Upper classes: LB LBF

Prostaglandin E₃

Structural Information
	7- [3R-Hydroxy-2R- (3S-hydroxyocta- (1-trans,5-cis) -dienyl) -5-oxocyclopentan-1R-yl ] -5-cis -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 Bergstroem_Set 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) Samuelsson_B
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
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

@@ Line 8: / Line 8: @@
 |SysName=7- [3R-Hydroxy-2R- (3S-hydroxyocta- (1-trans,5-cis) -dienyl) -5-oxocyclopentan-1R-yl ] -5-cis -heptenoic 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}}]]
 |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}}]]