LBF20207PG51

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Upper classes: LB LBF



Prostaglandin I2
LBF20207PG51.png
Structural Information
Systematic Name cis-5- [ 7R -Hydroxy-6R - (3S -hydroxyocten-trans-1-yl) -(1S,5R)-2-oxabicyclo [ 3.3.0 ] oct-3-ylidenpentanoic acid
Common Name
  • Prostaglandin I2
  • 5 (Z) - [ 7 (R) -Hydroxy-6 (R) - (3 (S) -hydroxyocten-1 (E) -yl) -1 (S) ,5 (R) -2-oxabicyclo [ 3.3.0 ] oct-3-ylidenpentanoic acid
Symbol PGI2
Formula C20H32O5
Exact Mass 352.224974134
Average Mass 352.46508
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]12)[C@H](O)C[C@H](OC(C2)=CCCCC(O)=O)1)CC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D=78°(C=0.8820, CHCl3) Johnson_RA et al.
Refractive Index
Solubility
Source In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin I2. Prostaglandin I2 is produced in blood vessels, lung and other tissues Moncada_S et al..
Chemical Synthesis Johnson_RA et al.
LBF20207PG51FT0001.gif
Metabolism Prostaglandin I2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2 by the catalysis of prostaglandin I synthase Pace-Asciak_CR et al. Tanabe_T et al.. Prostaglandin I2 is unstable and decomposes readily to 6-keto-prostaglandin F2 alpha . Its 2,3-dinor derivative is a major urinary metabolite Needleman_P et al..
Biological Activity Prostaglandin I2 is a potent anti-aggregatory agent for platelets, relaxes blood vessels, and enhances vascular permeability Whittle_BJ et al.. It binds to a receptor with 7 transmembrne domains (IP) coupled to a Gs protein Negishi_M et al..
Genetic Information cDNA Tanabe_T et al. and genomic DNA Yokoyama_C et al. for prostaglandin I synthase were cloned. cDNA for IP was isolated Negishi_M et al..
Note Stability:unstable in water around neutrality with a half life of about 5 min at 37°C and decomposes to 6-keto-PGF1 alpha Negishi_M et al..
Spectral Information
Mass Spectra 11,15-BIS(TRIMETHYLSILYL) ETHER METHYL ESTER ; 495(M+-CH3), 479, 439, 423, 349, 327, 323, 315, 313, 199, 173 Johnson_RA et al.
UV Spectra
IR Spectra METHYL ESTER ; LIQUID MELT ν 3370, 1740, 1695cm-1 Johnson_RA et al.
NMR Spectra 1-H-NMR(D2O, GLYCINE BUFFER, pH10.4) : δ 5.60(m, 2H, 13,14-CH), 4.66(m, 1H, 9-CH), 4.39(t, 1H, 5-CH), 4.15(q, 1H, 15-CH), 3.97(q, 1H, 11-CH), 2.20(t, 2H, 2-CH2) KotovychGet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG51 See above. Johnson_RA et al. 1978
n.a. LBF20207PG51 See above. Kotovych_G et al. 1980
n.a. LBF20207PG51 See above. Moncada_S et al. 1978
n.a. LBF20207PG51 See above. Needleman_P et al. 1986
n.a. LBF20207PG51 See above. Negishi_M et al. 1995
n.a. LBF20207PG51 See above. Negishi_M et al. 1995
n.a. LBF20207PG51 See above. Pace-Asciak_CR et al. 1983
n.a. LBF20207PG51 See above. Tanabe_T et al. 1995
n.a. LBF20207PG51 See above. Yokoyama_C et al. 1996


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