Structure Database (LMSD)
Common Name
8-iso-PGF2alpha III-EA
Systematic Name
N-([8S,12R]9S,11R,15S-trihydroxy-5Z,13E-prostadienoyl)-ethanolamine
Synonyms
- 8-iso-PGF2alpha-ethanolamine
3D model of 8-iso-PGF2alpha III-EA
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
It has been reported that anandamide (AEA) can be used directly by cyclooxygenase-2 and specific prostaglandin H2 (PGH2) isomerases to produce ethanolamide congeners of the classical PGs, including PGF2α.1 PGF2α ethanolamide has also been reported to be biosynthesized by this mechanism when AEA was infused into the lung and liver of fatty acid amide hydrolase-deficient mice.2 However, the accumulation of AEA can also lead to isoprostane-type peroxidative decomposition. 8-iso PGF2α ethanolamide is a standard that allows one to distinguish these non-enzymatic decomposition products from “prostamides” that could be of enzymatic origin.
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
XCVCLIRZZCGEMU-JJPTUHNDSA-N
InChi (Click to copy)
InChI=1S/C22H39NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18-,19+,20-,21+/m0/s1
SMILES (Click to copy)
C([C@@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC)/C=C\CCCC(NCCO)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
1
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
423.83
Topological Polar Surface Area
110.02
Hydrogen Bond Donors
5
Hydrogen Bond Acceptors
5
logP
3.50
Molar Refractivity
113.12
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Updated at
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