LBF20107PG01

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Upper classes: LB LBF



Prostaglandin E1
LBF20107PG01.png
Structural Information
Systematic Name 7- [3R- Hydroxy- 2R- (3S-hydroxy-trans-1-octenyl) -5-oxocyclopentan-1R-yl] -heptanoic acid
Common Name
  • Prostaglandin E1
  • (8R,11R,12R,13E,15S) -11,15-Dihydroxy-9-oxo-13-prostenoic acid
  • 7- [3R- Hydroxy- 2R- (3S -hydroxy-1(E) -octenyl) -5-oxocyclopentan-1R-yl] -heptanoic acid
Symbol PGE1
Formula C20H34O5
Exact Mass 354.240624198
Average Mass 354.48096000000004
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CCCCCCC(O)=O)[C@@H](CC1=O)O)CC
Physicochemical Information
Melting Point 115-117°C Bergstrom_S et al.
Boiling Point
Density
Optical Rotation [ α ]578=-61.6°(C=0.56, TETRAHYDROFURAN) Corey_EJ et al.
Refractive Index
Solubility DIETHYL ETHER, ETHYL ACETATE BergstromSet al. , METHANOL Struijk_MCB et al., TETRAHYDROFURAN Corey_EJ et al.
Source Prostaglandin E1 is contained in human seminal plasma in an amount of 25 microgram/ml Bergstrom_S , and has been found in ovine seminal plasma and seminal vesicle, human menstrual and amniotic flluid, human uterine endometrium, umbilical cord, placental vessels and decidua, frog spinal cord, rat adrenal, human and bovine thymus, frog intestine, rat fat tissue, and human phrenic nerve Horton_EW Speroff_L et al. Horton_EW Karim_SM et al. Karim_SM et al. Kirtland_SJ .
Chemical Synthesis Corey_EJ et al.
LBF20107PG01FT0001.gif
Metabolism Prostagalndin E1 is produced from H1 at almost the same rate of E2 synthesis from H2 by an enzyme of bovine seminal vesicle Ogino_N et al..
Biological Activity Prostaglandin E1 is generally considered as active as E2, and the biological activities of both compounds are compared in references Bergstrom_S et al. Horton_EW et al.. However, platelet aggregation is inhibited by prostaglandin E1 whereas prostaglandin E2 is much less active Bergstrom_S et al..
Genetic Information
Note
Spectral Information
Mass Spectra METHYL ESTER ; m/e 350, 332, 319, 301, 279 HambergMet al.
UV Spectra
IR Spectra METHYL ESTER ; ν 1726, 1717sh, 1699, 980 cm-1 HayashiMet al.
NMR Spectra 1H-NMR(CDCl3+DMSO-d6,TMS) : δ 5.70-5.51(m, 2H), 4.14-3.86(m, 2H), 2.72(d,d, 1H) HayashiMet al.. 13C-NMR(CHCl3-CH3OH, TMS) : δ 215.2(C-9), 176.7(C-1), 136.6(C-14), 131.9(C-13), 72.9(C-15), 71.6(C-11), 54.6(C-8), 54.2(C-12), 45.9(C-10), 36.9(C-16), 33.8(C-2), 31.5(C-18), 29.0(C-4), 28.6(C-5), 27.4(C-7), 26.3(C-6), 25.0(C-17), 24.5(C-3), 22.5(C-19), 13.8(C-20) LukacsGet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20107PG01 See above. Bergstrom_S 1967
n.a. LBF20107PG01 See above. Bergstrom_S et al. 1968
n.a. LBF20107PG01 See above. Bergstrom_S et al. 1960
n.a. LBF20107PG01 See above. Corey_EJ et al. 1969
n.a. LBF20107PG01 See above. Hamberg_M et al. 1966
n.a. LBF20107PG01 See above. Hayashi_M et al. 1975
n.a. LBF20107PG01 See above. Horton_EW 1965
n.a. LBF20107PG01 See above. Horton_EW 1969
n.a. LBF20107PG01 See above. Horton_EW et al. 1966
n.a. LBF20107PG01 See above. Karim_SM et al. 1968
n.a. LBF20107PG01 See above. Karim_SM et al. 1967
n.a. LBF20107PG01 See above. Kirtland_SJ 1988
n.a. LBF20107PG01 See above. Lukacs_G et al. 1973
n.a. LBF20107PG01 See above. Ogino_N et al. 1977
n.a. LBF20107PG01 See above. Speroff_L et al. 1970
n.a. LBF20107PG01 See above. Struijk_MCB et al. 1966


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