LBF20207PG25

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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	XPR1501
LipidMaps	LMFA03010002
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20207PG25

Prostaglandin F2α
Structural Information
Systematic Name	7- [ (3R,5S) -Dihydroxy-2R - (3S -hydroxy-trans-1-octenyl) cyclopentan-1R -yl] -cis-5-heptenoic acid
Common Name	Prostaglandin F2α 7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Symbol	PGF2α
Formula	C20H34O5
Exact Mass	354.240624198
Average Mass	354.48096000000004
SMILES	C(CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)[C@@H](C[C@@H]1O)O)CC
Physicochemical Information
Melting Point	25-35°C Bundy_GL et al.
Boiling Point
Density
Optical Rotation	[ α ]25 D   =23.8 °(C=1,THF) Corey_EJ et al.
Refractive Index
Solubility	ETHYL ACETATE, ACETONE, DIETHYLETHER Pike_JE et al.. STABILITIES: to be stable under neutral and basic conditions Karim_SM et al.
Source	Prostaglandin F2 alpha was found to be accummulating in human semen in an amount of about 2 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 F2 alpha .
Chemical Synthesis	Corey_EJ et al.
Metabolism	Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2 alpha . The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11 beta -prostaglandin F2 Urade_Y et al..
Biological Activity	Prostaglandin F2 alpha exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction Bergstrom_S et al.. Prostaglandin F2 alpha is a ligand to a receptor (FP) present in the cell membrane Negishi_M et al..
Genetic Information	cDNA for prostaglandin F synthase was cloned from bovine lung Urade_Y et al.. cDNA for prostaglandin F2 alpha receptor (FP) was cloned, and its 7ptransmembrane structure was reported Negishi_M et al..
Note
Spectral Information
Mass Spectra	354(M+), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 HorvathG
UV Spectra
IR Spectra	NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm-1 PikeJEet al.
NMR Spectra	1H-NMR(d6-ACETONE) : δ 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) Pike_JE et al.. 13C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 LukacsGet al.
Other Spectra
Chromatograms

[hide]Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF20207PG25 See above. Bergstrom_S 1967 n.a. LBF20207PG25 See above. Bergstrom_S et al. 1968 n.a. LBF20207PG25 See above. Bundy_GL et al. 1972 n.a. LBF20207PG25 See above. Corey_EJ et al. 1970 n.a. LBF20207PG25 See above. Horvath_G 1976 n.a. LBF20207PG25 See above. Karim_SM et al. 1968 n.a. LBF20207PG25 See above. Lukacs_G et al. 1973 n.a. LBF20207PG25 See above. Negishi_M et al. 1995 n.a. LBF20207PG25 See above. Pike_JE et al. 1969 n.a. LBF20207PG25 See above. Urade_Y et al. 1995

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