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

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Identification of the major urinary metabolite of the F2-isoprostane 8-iso-prostaglandin F2alpha in humans.,
J Biol Chem, 1996
Pubmed ID: 8702808

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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

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Created at
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Updated at
10th Jan 2025