LBF20207PG27

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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	XPR1601
LipidMaps	LMFA03010009
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20207PG27

Prostaglandin G2
Structural Information
Systematic Name	7- [2R- (3S -Hydroxy-trans-1-octenyl) -(1R,4S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3R-yl] -cis-5-heptenoic acid
Common Name	Prostaglandin G2 7- [ 2R- (3S -Hydroxy-1-(E)-octenyl) -(1R,4S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3R-yl ] -5(Z)-heptenoic acid
Symbol	PGG2
Formula	C20H32O6
Exact Mass	368.219888756
Average Mass	368.46448
SMILES	C(CC[C@@H](OO)C=C[C@@H]([C@H]21)[C@@H](CC=CCCCC(O)=O)[C@@H](OO2)C1)CC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	Prostaglandin G2 is produced by bis-dioxygenation and cyclization of arachidonic acid as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues Pace-Asciak_CR et al. .
Chemical Synthesis	Porter_NA et al.
Metabolism	Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 . The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds Smith_WL et al. Herschman_HR
Biological Activity	Prostaglandin G2 is a metabolic intermediate, but the compound as such has biological activities of bronchoconstriction and vasoconstriction Moncada_S et al. Chijimatsu_Y et al..
Genetic Information	cDNA and genomic DNA each for cyclooxygenas-1 and 2 were cloned Funk_CD .
Note	Stability:unstable in water around neutrality with a half life of about 5 min at 37°C and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid Nugteren_DH et al..
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra	13C-NMR : δ 84.6(C15) Porter_NA et al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF20207PG27 See above. Chijimatsu_Y et al. 1977 n.a. LBF20207PG27 See above. Funk_CD 1993 n.a. LBF20207PG27 See above. Herschman_HR 1996 n.a. LBF20207PG27 See above. Moncada_S et al. 1978 n.a. LBF20207PG27 See above. Nugteren_DH et al. 1973 n.a. LBF20207PG27 See above. Pace-Asciak_CR et al. 1983 n.a. LBF20207PG27 See above. Porter_NA et al. 1980 n.a. LBF20207PG27 See above. Smith_WL et al. 1996