LBF20207PG23

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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	XPR1401
LipidMaps	LMFA03010003
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20207PG23

Prostaglandin E2
Structural Information
Systematic Name	7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl-5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Common Name	Prostaglandin E2 7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl-5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Symbol	PGE2
Formula	C20H32O5
Exact Mass	352.224974134
Average Mass	352.46508
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	65-66°C Corey_EJ et al.
Boiling Point
Density
Optical Rotation	[a]XD26=-61.0°(C=1.0, TETRAHYDROFURAN) Corey_EJ et al.
Refractive Index
Solubility	ETHYL ACETATE,THF,CHLOROFORM Donaldson_RE et al. Sih_CJ et al.. STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions Karim_SM et al. Pike_JEet al.
Source	Prostaglandin E2 was found to be accummulating in human semen in an amount of about 13 microgram per ml Bergstrom_S . In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin E2.
Chemical Synthesis	Corey_EJ et al.
Metabolism	Prostaglandin E2 is produced from arachidonic acid via prostaglandins G2 and H2 by the catalyses of prostaglandin endoperoxide synthase (cyclooxygenase) Smith_WL et al. and prostaglandin E synthase Urade_Y et al.. Two isoforms of the cyclooxygnease enzyme responsible for prostaglandin H2 synthesis are present. Cyclooxygenase-1 is constitutively found in most mammalian tissues, while cyclooxygnease-2 is induced rapidly and transiently in physiological and pathological events, especially in inflammation Smith_WL et al.. The biological activities of prostaglandin E2 are lost by oxidation of its 15-hydroxyl group catalyzed by 15-hydroxyprostaglandin dehydrogenase Hansen_HS .
Biological Activity	Prostaglandin E2 exhibits various biological activities such as vasodilatation, uterine contraction, gastrointestinal contraction, bronchodilatation, diuresis, pyrexia, inhibition of gastric secretion, bone resorption and immunosuppression Bergstrom_S et al.. Prostaglandin E2 is a ligand to receptors present in the cell membrane, and there are at least 4 subtypes of its receptor. Different tissue distributions and signal transductions of these receptor subtypes explain a variety of biological activities of prostaglandin E2 Negishi_M et al..
Genetic Information
Note
Spectral Information
Mass Spectra	d,l-mixture ; 334(M+-18), 316, 298, 190 Chen_SML et al.
UV Spectra
IR Spectra	d,l-mixture ; 3400, 1710, 970cm-1 Chen_SML et al.
NMR Spectra	13C-NMR(CDCl3) : 214.71(C9),178.39(C1), 136.62(C14), 131.52(C13), 130.91(C5), 126.69(C6), 73.19(C15), 72.13(C11), 54.55(C12), 53.51(C8), 46.23(C10), 37.00 (C16), 33.56(C2), 31.73(C18), 26.47(C4), 25.20(C7,17), 24.60(C3), 22.64(C19), 14.04. Donaldson_RE et al.. 1H-NMR(CDCl3) : d5.67(dd, J=6.6Hz, 15.4, 1H, 14-CH), 5.57(dd, J=8.1, 15.4Hz, 1H, 13-CH), 5.40(m, 2H, 5.6-CH), 4.12(q, J=6.5, 6.7, 6.8Hz, 1H, 15-CH), 4.06(q, J=8.1, 8.2, 8.3Hz, 1H, 11-CH), 2.72(dd, J= Donaldson_RE et al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF20207PG23 See above. Bergstrom_S 1967 n.a. LBF20207PG23 See above. Bergstrom_S et al. 1968 n.a. LBF20207PG23 See above. Chen_SML et al. 1978 n.a. LBF20207PG23 See above. Corey_EJ et al. 1970 n.a. LBF20207PG23 See above. Donaldson_RE et al. 1983 n.a. LBF20207PG23 See above. Funk_CD 1993 n.a. LBF20207PG23 See above. Hansen_HS 1976 n.a. LBF20207PG23 See above. Herschman_HR 1996 n.a. LBF20207PG23 See above. Karim_SM et al. 1968 n.a. LBF20207PG23 See above. Negishi_M et al. 1995 n.a. LBF20207PG23 See above. Pike_JE et al. 1969 n.a. LBF20207PG23 See above. Sih_CJ et al. 1975 n.a. LBF20207PG23 See above. Smith_WL et al. 1996 n.a. LBF20207PG23 See above. Urade_Y et al. 1995