Structure Database (LMSD)
Common Name
8-isoPGF2alpha-d4
Systematic Name
9α,11α,15S-trihydroxy-(8β)-prosta-5Z,13E-dien-1-oic-3,3,4,4-d4 acid
Synonyms
- 9S,11R,15S-trihydroxy-5Z,8-iso Prostaglandin F2alpha-d4
- 13E-prostadienoic acid-cyclo[8S,12R]-d4
- iPF2alpha-III-d4
- 8-Isoprostane-d4
- 15-F2t-Isoprostane-d4
- 8-epi PGF2alpha-d4
3D model of 8-isoPGF2alpha-d4
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
8-iso PGF2α-d4 is intended for use as an internal standard for the quantification of 8-iso PGF2α by GC- or LC-mass spectrometry. 8-iso Prostaglandin F2α (8-iso PGF2α) is an isoprostane produced by the non-enzymatic peroxidation of arachidonic acid in membrane phospholipids.1,2,3 It circulates in human plasma in two distinct forms - esterified in LDL phospholipids and as the free acid. The ratio of these two forms is approximately 2:1, with a total plasma 8-iso PGF2α level of about 150 pg/ml in normal volunteers. In normal human urine, 8-iso PGF2α levels are about 180-200 pg/mg of creatinine.1,2 8-iso PGF2α is a weak TP receptor agonist in vascular smooth muscle.4 Conversely, 8-iso PGF2α inhibits platelet aggregation induced by U-46619 (10−6 M) and I-BOP (3 x 10−7 M) with IC50 values of 1.6 x 10−6 M and 1.8 x 10−6 M, respectively.3
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)
PXGPLTODNUVGFL-FLRLWOSLSA-N
InChi (Click to copy)
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1/i5D2,8D2
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\C([2H])([2H])C([2H])([2H])CC(O)=O
Other Databases
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
3rd Dec 2024
Updated at
5th Dec 2024