Structure Database (LMSD)

Common Name
15R-PGE1
Systematic Name
9-oxo-11R,15R-dihydroxy-13E-prostaenoic acid
Synonyms
  • 15R-Prostaglandin E1
LM ID
LMFA03010055
Formula
C20H34O5
Exact Mass
Calculate m/z
354.240625
Sum Composition
FA 20:3;O3
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

15(R)-PGE1 is the “unnatural” C-15 stereoisomer of PGE1. It is essentially inactive biologically when compared to PGE1.1 It is a non-competitive inhibitor of 15-hydroxy PGDH with an IC50 of 189 µM.2

This information has been provided by Cayman Chemical

References

1. Nakano, J. Relationship between the chemical structure of prostaglandins and their vasoactivities in dogs. Br. J. Pharmacol. 44(1), 63-70 (1972).
2. Jarabak, J., and Braithwaite, S.S. Kinetic studies on a 15-hydroxyprostaglandin dehydrogenase from human placenta. The reaction mechanism and the mechanism of action of various inhibitors. Arch. Biochem. Biophys. 177, 245-254 (1976).

String Representations

InChiKey (Click to copy)
GMVPRGQOIOIIMI-CHCORRSHSA-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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17-,19-/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O

Other Databases

CHEBI ID
182985
LIPIDBANK ID
XPR1737
PubChem CID
5283056
Cayman ID
13710

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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Updated at
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