LBF20107PG02

LipidBank Top (トップ)

Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

Journals (雑誌一覧)

How to edit (ページの書き方)

Upper classes: LB LBF

IDs and Links
LipidBank	XPR1430
LipidMaps	LMFA03010012
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20107PG02

6-keto Prostaglandin E1
Structural Information
Systematic Name	7- [3R- Hydroxy- 2R- (3S -hydroxy-1-trans -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.
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