Structure Database (LMSD)
Common Name
8-iso-13,14-dihydro-15-keto-PGF2alpha
Systematic Name
9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R]
Synonyms
LM ID
LMFA03110004
Formula
Exact Mass
Calculate m/z
354.240626
Sum Composition
Status
Curated
3D model of 8-iso-13,14-dihydro-15-keto-PGF2alpha
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
8-iso-13,14-dihydro-15-keto Prostaglandin F2α (8-iso-13,14-dihydro-15-keto PGF2α) is a metabolite of the isoprostane, 8-isoprostane (8-iso PGF2α), in rabbits, monkeys and humans.1 8-iso PGF2α is a PG-like product of non-specific lipid peroxidation.2 In both humans and monkeys, exogenously infused 8-isoprostane is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation.1 A similar pattern is observed when tritiated 8-isoprostane is infused into rabbits.3 Early in the infusion (within 10 minutes) 8-iso-13,14-dihydro-15-keto PGF2α was a significant component of the metabolite profile, which was comprised mostly of dinor 8-isoprostane metabolites. 8-iso-13,14-dihydro-15-keto PGF2α weakly inhibits the U-46619 or collagen-induced aggregation of human platelets, although a number of the E-series isoprostanes are much more potent in this assay.4
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
VKTIONYPMSCHQI-JPRPWBOBSA-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/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17+,18-,19+/m0/s1
SMILES (Click to copy)
[C@H]1(CCC(=O)CCCCC)[C@H](O)C[C@H](O)[C@H]1C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
378.23
Topological Polar Surface Area
94.83
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
4.05
Molar Refractivity
98.26
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Created at
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Updated at
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