Structure Database (LMSD)
Common Name
2,3-dinor-PGE1
Systematic Name
9-oxo-11R,15S-dihydroxy-2,3-dinor-13E-prostenoic acid
Synonyms
- 2,3-dinor-Prostaglandin E1
LM ID
LMFA03010169
Formula
Exact Mass
Calculate m/z
326.209325
Sum Composition
Status
Curated
3D model of 2,3-dinor-PGE1
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Prostaglandin E1 (PGE1) is not a major naturally occurring prostaglandin, but it is widely administered clinically for several indications including peripheral occlusive vascular disease, erectile dysfunction and in neonatal cardiology.1,2 The metabolism of PGE1 is normally initiated by oxidation at C-15, resulting in 13,14-dihydro-15-keto PGE1 as the major metabolite. However, inhibition of this pathway or saturation by excess substrate could theoretically lead to enhanced production of 2,3-dinor metabolites, including 2,3-dinor PGE1. The biological activity of 2,3-dinor PGE1 has not been published. Cayman Chemical is a leading supplier of prostaglandins and their metabolites, and is currently the exclusive manufacturer of 2,3-dinor PGE1.
This information has been provided by Cayman Chemical
References
2. Hoshi, K. Approved indications of lipo-PGE1 in Japan. Adv. Drug Deliv. Rev. 20(2-3), 171-176 (1996).
String Representations
InChiKey (Click to copy)
GTUGBRJEKVKOKQ-LRSAKWJDSA-N
InChi (Click to copy)
InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h10-11,13-15,17,19,21H,2-9,12H2,1H3,(H,22,23)/b11-10+/t13-,14+,15+,17+/m0/s1
SMILES (Click to copy)
C(CCCC[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)CC1=O)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
1
Aromatic Rings
0
Rotatable Bonds
11
Van der Waals Molecular Volume
343.63
Topological Polar Surface Area
94.83
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.27
Molar Refractivity
89.03
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Updated at
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