LBF20303PG03

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Upper classes: LB LBF



Prostaglandin E3
LBF20303PG03.png
Structural Information
Systematic Name 7- [3R-Hydroxy-2R- (3S-hydroxyocta- (trans-1,cis-5) -dienyl) -5-oxocyclopentan-1R-yl ] -cis-5-heptenoic acid
Common Name
  • 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
Symbol 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
Melting Point 84.5-85.5°C Okamoto K et al.
Boiling Point
Density
Optical Rotation [ α ]24
D
   =-48.9°(C=1.2, TETRAHYDROFURAN) Corey_EJ et al.
Refractive Index
Solubility TETRAHYDROFURAN Corey_EJ et al.
Source 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..
Chemical Synthesis Corey_EJ et al.
LBF20303PG03FT0001.gif
Metabolism
Biological Activity As presented in Table 1 of reference Bergstrom_S et al., prostaglandin E3 is 1/10-1/2 as active as prostaglandin E2.
Genetic Information
Note
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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