Structure Database (LMSD)

Common Name
8,12-iso-iPF2alpha-VI-d11
Systematic Name
5,9S,11R-trihydroxy-6E,14Z-prostadienoic acid-cyclo[8R,12S]-(d11)
Synonyms
  • 5(R,S)-5-F2c-IsoP-d11
  • (12alpha)-5,9alpha,11alpha-trihydroxy-prosta-6E,14Z-dien-1-oic-16,16,17,17,18,18,19,19,20,20,20-d11 acid
  • 8,12-iso-Isoprostane-F2alpha-VI-d11
  • 12-iso-5,6E,14Z-PGF2alpha-d11
  • 12-iso-5,6E,14Z-Prostaglandin F2alpha-d11
LM ID
LMFA03110364
Formula
Exact Mass
Calculate m/z
365.30967
Status
Curated

Classification

Biological Context

8,12-iso-isoprostane F2α-VI-d11 (8,12-iso-iPF2α-VI-d11) contains 11 deuterium atoms at the 16, 16', 17, 17', 18, 18', 19, 19', 20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of 8,12-iso-iPF2α-VI by GC- or LC-mass spectrometry. The relative abundance of deuterium atoms incorporated into each molecule has not been determined. Cayman certifies that less that 1% of the product has no deuterium incorporation (<1% d0). Isoprostanes are non-enzymatic, non-cyclooxygenase prostanoid products of peroxidative damage to membrane lipids.1 Among the many isoprostane isomers, 8,12-iso-iPF2α-VI has been demonstrated to be one of the predominant isomers formed and is also present in urine as one of the major isoprostane products.2 8,12-iso-iPF2α-VI-d11 is a deuterated internal standard for use in isoprostane quantitation by mass spec modalities. The compound is diastereomeric at C-5, but is otherwise an optically active, single enantiomer.

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
RZCPXIZGLPAGEV-JVUJZTPFSA-N
InChi (Click to copy)
InChI=1S/C20H34O5/c1-2-3-4-5-6-7-10-16-17(19(23)14-18(16)22)13-12-15(21)9-8-11-20(24)25/h6-7,12-13,15-19,21-23H,2-5,8-11,14H2,1H3,(H,24,25)/b7-6-,13-12+/t15?,16-,17+,18+,19-/m0/s1/i1D3,2D2,3D2,4D2,5D2
SMILES (Click to copy)
C(CCCC(O)/C=C/[C@H]1[C@@H](O)C[C@@H](O)[C@H]1C/C=C\C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])(=O)O

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings
Rotatable Bonds 12
Van der Waals Molecular Volume 378.23
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 3.90
Molar Refractivity 99.68

Admin

Created at
15th May 2025
Updated at
15th May 2025