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
LM ID
LMFA03110015
Formula
Exact Mass
Calculate m/z
397.282824
Status
Curated

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

CHEBI ID
PubChem CID
Cayman ID

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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