LBF20107PG02

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Upper classes: LB LBF



6-keto Prostaglandin E1
LBF20107PG02.png
Structural Information
Systematic Name 7- [3R- Hydroxy- 2R- (3S-hydroxy-trans-1-octenyl) -5-oxocyclopentan-1R-yl] -oxoheptanoic acid
Common Name
  • 6-keto Prostaglandin E1
  • 7- [3R- Hydroxy- 2R- (3S -hydroxy-1-(E) -octenyl) -5-oxocyclopentan-1R-yl] -oxoheptanoic acid
Symbol 6-KETO-PGE1
Formula C20H32O6
Exact Mass 368.219888756
Average Mass 368.46448
SMILES C(CC[C@@H](O)C=C[C@H]([C@@H](CC(=O)CCCCC(O)=O)1)[C@@H](CC1=O)O)CC
Physicochemical Information
Melting Point 65°C Tanaka_T et al.
Boiling Point
Density
Optical Rotation [ α ]X20
D
   =-50°(C=1.55, METHANOL) TanakaTet al.
Refractive Index
Solubility METHANOL, CHLOROFORM TanakaTet al.
Source There were reports of prolonged biological activity of chemically unstable prostaglandin I2, which suggested a possible transformation of prostaglandin I2 to a more stable metabolite with potent bioactivity Wong_PY et al.. Further investigations led to the discovery of 6-keto-prostaglandin E1.
Chemical Synthesis Tanaka_T et al.
LBF20107PG02FT0001.gif
Metabolism A potential role of 9-hydroxyprostaglandin dehydrogenase was demonstrated in the transformation of prostaglandin I2 to 6-keto-prostaglandin E1 Wong_PY et al..
Biological Activity 6-Keto-prostaglandin E1 is a stable metabolite. The compound inhibits platelet aggregation with activity comparable or greater than prostaglandin D2 although less potent than prostaglandin I2. Its vasodilatory and hypotensive activities, bronchodilatory property, and inhibition of gastric acid secretion were reported Moore_PK et al..
Genetic Information
Note
Spectral Information
Mass Spectra DIRECT EXPOSURE AMMONIA CI, POSITIVE : 386(M++18), 368(M+), 351, 350, 244, 136. NEGATIVE : 368(M+) ,350, 338, 332 Cepa_SR et al.
UV Spectra
IR Spectra KBr: ν 3400, 1740, 1720, 1710, 1245, 1160, 1075, 970 cm-1 TanakaTet al.
NMR Spectra 1H-NMR(CDCl3) : δ 5.58(m, 2H, 13,14-CH), 4.09(m, 1H, 11-CH), 4.02(m, 1H, 15-CH), 2.7(2H, 7-CH), 2.69(IH, 10 β -CH), 2.45-2.47(m, 3H, 5,8,12-CH), 2.29(1H, 10 α -CH), 2.28(2H, 2-CH), 1.58 - 1.32(12H), 0.91(t, 3H, 20-CH3) KotovychGet al.. METHYL ESTER ; 13C-NMR(CDCl3) : 216.6, 208.4, 173.8, 138.0, 126.5, 72.3, 51.5, 44.6, 45.7, 42.4, 37.6, 33.8, 31.8, 25.2, 24.5, 23.4, 22.6, 14.0 TanakaTet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20107PG02 See above. Cepa_SR et al. 1984
n.a. LBF20107PG02 See above. Kotovych_G et al. 1982
n.a. LBF20107PG02 See above. Moore_PK et al. 1983
n.a. LBF20107PG02 See above. Tanaka_T et al. 1987
n.a. LBF20107PG02 See above. Wong_PY et al. 1980


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