Structure Database (LMSD)

Common Name
2,3-Dinor-8-iso-PGF2alpha
Systematic Name
9S,11R,15S-trihydroxy-2,3-dinor-5Z,13E-prostadienoic acid-cyclo[8S,12R]
Synonyms
LM ID
LMFA03110010
Formula
C18H30O5
Exact Mass
Calculate m/z
326.209325
Sum Composition
FA 18:3;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Isoprostanes [FA0311]

Biological Context

8-iso Prostaglandin F2α (8-iso PGF2α; 8-isoprostane) is a prostaglandin-like product of non-specific lipid peroxidation.1 2,3-dinor-8-iso PGF2α is a metabolite of 8-iso PGF2α in humans and rats.2 In these species, exogenously infused 8-iso PGF2α is converted to 2,3-dinor-8-iso PGF1α and (2,3-dinor-8-iso PGF2α.2,3 Rat hepatocytes further metabolize 8-iso PGF2α to another β-oxidation product, 2,3,4,5-tetranor-8-iso PGF2α.2 2,3-dinor-8-iso PGF2α is present in normal human urine at concentrations of 200-300 pg/ml.2 Its concentration is increased in conditions of oxidative injury (for example, smoking), and correlates well with that of the parent isoprostane, 8-iso PGF2α.2

This information has been provided by Cayman Chemical

References

1. Morrow, J.D., Hill, K.E., Burk, R.F., et al. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc. Natl. Acad. Sci. USA 87(23), 9383-9387 (1990).
2. Roberts, L.J., II, Moore, K.P., Zackert, W.E., et al. Identification of the major urinary metabolite of the F2-isoprostane 8-iso-prostaglandin F2α in humans. The Journal of Biological Chemisty 271(34), 20617-20620 (1996).
3. Chiabrando, C., Valagussa, A., Rivalta, C., et al. Identification and measurement of endogenous β-oxidation metabolites of 8-epi-prostaglandin F2α. The Journal of Biological Chemisty 274(3), 1313-1319 (1999).

String Representations

InChiKey (Click to copy)
IDKLJIUIJUVJNR-JSEKUSAISA-N
InChi (Click to copy)
InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h5-6,10-11,13-17,19-21H,2-4,7-9,12H2,1H3,(H,22,23)/b6-5-,11-10+/t13-,14-,15+,16-,17+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@H](O)[C@H]1C/C=C\CC(=O)O

Other Databases

KEGG ID
C14794
CHEBI ID
34230
PubChem CID
9548881
Cayman ID
16290

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 343.63
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 3.12
Molar Refractivity 90.45

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Updated at
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