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 F_2α
Structural Information
Systematic Name	7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenylcyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Common Name	PROSTAGLANDIN F_2α 7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenylcyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Symbol	PGF2a
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	[a]XD25=23.8 °(C=1,THF) Corey_EJ et al.
Refractive Index
Solubility	ETHYL ACETATE, ACETONE, DIETHYLETHER Pike_JEet al.. STABILITIES: to be stable under neutral and basic conditions Karim_SM et al.
Source	Prostaglandin F2a 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 F2a.
Chemical Synthesis	Corey_EJ et al.
Metabolism	Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2a. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11b-prostaglandin F2 Urade_Y et al..
Biological Activity	Prostaglandin F2a exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction Bergstrom_S et al.. Prostaglandin F2a 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 F2a 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 Pike_JEet al.
NMR Spectra	1H-NMR(d6-ACETONE) : d 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) Pike_JEet 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

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