Structure Database (LMSD)
Common Name
6alpha-PGI1
Systematic Name
6R,9S-epoxy-11R,15S-dihydroxy-13E-prostaenoic acid
Synonyms
- 6alpha-Prostaglandin I1
LM ID
LMFA03010128
Formula
Exact Mass
Calculate m/z
354.240625
Sum Composition
Status
Curated
3D model of 6alpha-PGI1
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
6α-Prostaglandin I1 (6α-PGI1) is a stable Prostaglandin I2 (PGI2) analog resistant to hydrolysis in aqueous solutions. 6α-PGI1 promotes cyclic AMP accumulation in human thyroid slices and cells in a concentration dependent manner. However, it is about 10-fold less potent than the β-isomer and 100-fold less potent than PGI2 in eliciting the response.1 6α-PGI1 exhibits an IC50 of 350 ng/ml for inhibition of ADP-induced platelet aggregation, which is nearly 900-fold higher than that observed for PGI2 (0.4 ng/ml).2
This information has been provided by Cayman Chemical
References
2. Whittle, B.J.R., and Moncada, S. Prostacyclin and its analogues for the therapy of thromboembolic disorders. Adv. Exp. Med. Biol. 164, 193-209 (1984).
String Representations
InChiKey (Click to copy)
RJADQDXZYFCVHV-WDONHGPHSA-N
InChi (Click to copy)
InChI=1S/C20H34O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h10-11,14-19,21-22H,2-9,12-13H2,1H3,(H,23,24)/b11-10+/t14-,15+,16+,17+,18+,19-/m0/s1
SMILES (Click to copy)
[C@@H]1(O)C[C@@H]2O[C@H](CCCCC(=O)O)C[C@@H]2[C@H]1/C=C/[C@@H](O)CCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
2
Aromatic Rings
0
Rotatable Bonds
11
Van der Waals Molecular Volume
368.51
Topological Polar Surface Area
89.06
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
4.43
Molar Refractivity
98.32
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Updated at
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