Structure Database (LMSD)

Common Name
13,14-dihydro-6,15-diketo-PGF1alpha
Systematic Name
6,15-dioxo-9S,11R-dihydroxyprostanoic acid
Synonyms
  • 13,14-dihydro-6,15-diketo-Prostaglandin F1alpha
LM ID
LMFA03010013
Formula
C20H34O6
Exact Mass
Calculate m/z
370.23554
Sum Composition
FA 20:3;O4
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

Biological Context

6,15-diketo-13,14-dihydro PGF1α is a metabolite of PGI2. It was shown to enhance intracellular cAMP and cholesterol catabolism in bovine arterial smooth muscle cells.1

This information has been provided by Cayman Chemical

References

1. Etingin, O.R., Weksler, B.B., and Hajjar, D.P. Cholesterol metabolism is altered by hydrolytic metabolites of prostacyclin in arterial smooth muscle cells. J. Lipid Res. 27, 530-536 (1986).

String Representations

InChiKey (Click to copy)
KBHLXKOKUVJZIS-MKXGPGLRSA-N
InChi (Click to copy)
InChI=1S/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h16-19,23-24H,2-13H2,1H3,(H,25,26)/t16-,17-,18-,19+/m1/s1
SMILES (Click to copy)
[C@H]1(CCC(=O)CCCCC)[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(=O)O

Other Databases

HMDB ID
HMDB01979
LIPIDBANK ID
XPR1715
PubChem CID
174013
Cayman ID
15270

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 384.38
Topological Polar Surface Area 111.90
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 3.23
Molar Refractivity 98.65

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Updated at
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