LBF20107PG03

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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	XPR1500
LipidMaps	LMFA03010137
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20107PG03

PROSTAGLANDIN F_1α
Structural Information
Systematic Name	7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -heptanoic acid / (8R,9S,11R,13E,15S) -9,11,15-Trihydroxyprost-13-enoic acid
Common Name	PROSTAGLANDIN F_1α 7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) cyclopentan-1 (R) -yl ] -heptanoic acid (8R,9S,11R,13E,15S) -9,11,15-Trihydroxyprost-13-enoic acid
Symbol	PGF1 alpha
Formula	C20H36O5
Exact Mass	356.256274262
Average Mass	356.49684
SMILES	C(CC[C@@H](O)C=C[C@H]([C@H]1CCCCCCC(O)=O)[C@@H](C[C@@H]1O)O)CC
Physicochemical Information
Melting Point	102-103°C
Boiling Point
Density
Optical Rotation	[ α ]X25 D   =+30°(ETHANOL) Pike_JEet al.
Refractive Index
Solubility	DIETHYL ETHER, ETHYL ACETATE, METHANOL , ETHANOL Pike_JEet al.
Source	Prostaglandin F1 alpha is contained in human seminal plasma in an amount of 3.6 microgram/ml Bergstrom_S , and is detected in ovine seminal plasma and seminal vesicle, human amniotic fluid, umbilical cord, placental vessels and decidua, frog spinal cord and intestine, and rat adrenal Horton_EW .
Chemical Synthesis	Miyano_M et al.
Metabolism
Biological Activity	In terms of contraction of gastrointestinal smooth muscles, prostaglandin F1 alpha was repoprted to be about 10 times less active than prostaglandin F2 alpha Horton_EW . Reference Bergstrom_S et al. contains a table for comparison of biological activities of various prostaglandins including F1 alpha .
Genetic Information
Note
Spectral Information
Mass Spectra	m/e 356(M+), 338, 320 Ramwell_PW et al.
UV Spectra
IR Spectra	d,l-PGF1 α  ; KBr : ν 3330, 1716, 967 cm-1 MiyanoMet al.
NMR Spectra	1H-NMR(ACETONE-d6, TMS) : δ 5.50(2H, 13-,14-CH), 3.75-4.3(m, 3H), 0.88(t, 3H) Ramwell_PW et al.1H-NMR(CD3OD, TMS, 300MHz): δ 4.10(1H, 9-CH), 3.81(1H, 11-CH), 2.36(1H, 10 β -CH), 1.57(1H, 10 α -CH) De_ClercqPet al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF20107PG03 See above. Bergstrom_S 1967 n.a. LBF20107PG03 See above. Bergstrom_S et al. 1968 n.a. LBF20107PG03 See above. Bergstrom_S et al. 1960 n.a. LBF20107PG03 See above. De_Clercq_P et al. 1977 n.a. LBF20107PG03 See above. Horton_EW 1965 n.a. LBF20107PG03 See above. Horton_EW 1969 n.a. LBF20107PG03 See above. Miyano_M et al. 1972 n.a. LBF20107PG03 See above. Pike_JE et al. 1969 n.a. LBF20107PG03 See above. Ramwell_PW et al. 1971