Structure Database (LMSD)
Common Name
2,3-dinor-5,6-dihydro-15-F2t-IsoP
Systematic Name
9S,11R,15S-trihydroxy-2,3-dinor-13E-prostaenoic acid-cyclo[8S,12R]
Synonyms
- 2,3-dinor-5,6-dihydro-15-F2t-Isoprostane
- 2,3-dinor-iPF1alpha-III
- 2,3-dinor-8-iso PGF1alpha
- 13-F1t-PhytoP-GLA
LM ID
LMFA03010154
Formula
Exact Mass
Calculate m/z
328.224976
Sum Composition
Status
Curated
3D model of 2,3-dinor-5,6-dihydro-15-F2t-IsoP
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
2,3-dinor-8-iso Prostaglandin F1α (2,3-dinor-8-iso PGF1α) is an isoprostane and active metabolite of arachidonic acid and the platelet aggregation inhibitor 8-iso PGF2α .1,2 It is formed by the non-enzymatic, free radical peroxidation of arachidonic acid.1 2,3-dinor-8-iso PGF1α induces vasoconstriction in isolated porcine retinal and brain microvessels (EC50s = 12.8 and 18.5 nM, respectively) but does not induce contraction of isolated rat aortic rings when used at a concentration of 31 µM.1,3 It increases thromboxane B2 (TXB2) levels in isolated porcine brain slices when used at a concentration of 1 µM, an effect that can be reversed by the thromboxane A synthase inhibitor CGS 12970, the voltage-gated calcium channel inhibitor SKF 96365 , or nicotinic acetylcholine receptor (nAChR) antagonist α-conotoxin.1
This information has been provided by Cayman Chemical
References
1. 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. Hou, X., Roberts, L.J., 2nd., Taber, D.F., et al. 2,3-Dinor-5,6-dihydro-15-F2t-isoprostane: A bioactive prostanoid metabolite. Am. J. Physiol. Regul. Integr. Comp. Physiol. 281(2), R391-R400 (2001).
References
String Representations
InChiKey (Click to copy)
XHHYJZGDOMKLEE-RLDLTEIJSA-N
InChi (Click to copy)
InChI=1S/C18H32O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h10-11,13-17,19-21H,2-9,12H2,1H3,(H,22,23)/b11-10+/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]1CCCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
1
Aromatic Rings
0
Rotatable Bonds
11
Van der Waals Molecular Volume
346.27
Topological Polar Surface Area
97.99
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
5
logP
3.35
Molar Refractivity
90.54
Admin
Created at
-
Updated at
10th Jan 2025