LBF20107PG01

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	XPR1400
LipidMaps	LMFA03010134
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20107PG01

Prostaglandin E1
Structural Information
Systematic Name	7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -5-oxocyclopentan-1 (R) -yl ] -heptanoic acid / (8R,11R,12R,13E,15S) -11,15-Dihydroxy-9-oxo-13-prostenoic acid
Common Name	Prostaglandin E1 7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -5-oxocyclopentan-1 (R) -yl ] -heptanoic acid (8R,11R,12R,13E,15S) -11,15-Dihydroxy-9-oxo-13-prostenoic 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
Boiling Point
Density
Optical Rotation	[ α ]578=-61.6°(C=0.56, TETRAHYDROFURAN) Corey_EJ et al.
Refractive Index
Solubility	DIETHYL ETHER, ETHYL ACETATE , 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.
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.. 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