Accession NumberHMDB05844
Common_Name8-isoprostaglandin E2
Description8-isoprostaglandin E2 is an isoprostane generated from the endoperoxide intermediate 8-iso-PGH2. Isoprostanes (IsoPs) are formed in vivo from the free radical-catalyzed peroxidation of arachidonate independent of cyclooxygenase (COX). Although the structures of these compounds are very similar to COX-derived prostaglandins (PGs), an important distinction between IsoPs and PGs is that IsoP bicycloendoperoxide intermediates contain side chains that are predominantly (>90%) oriented cis in relation to the prostane ring because the generation of these intermediates is favored kinetically. In contrast to other types of prostanoids, E2/D2-IsoPs are beta-hydroxyketone-containing compounds that can undergo reversible keto-enol tautomerization under both acidic and basic conditions, allowing rearrangement of the side chains that are initially cis to the more stable trans-configuration. (PMID: 12746435)
Chemical_IUPAC_Name(Z)-7-[(1S,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
Chemical FormulaC20H32O5
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Predicted 1H NMR SpectrumDownload
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Predicted 13C NMR SpectrumDownload
Predicted 13C NMR PeaklistDownload
Sample ConcentrationNot Available
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