Structure Database (LMSD)
Common Name
ent-PGE2
Systematic Name
9-oxo-11S,15R-dihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12S]
Synonyms
LM ID
LMFA03110106
Formula
Exact Mass
Calculate m/z
352.224975
Sum Composition
Status
Curated
3D model of ent-PGE2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Enzymatically-derived PGE2 is an optically pure compound whereas PGE2 derived from the free radical-catalyzed peroxidation of arachidonate is a racemic mixture. Ent-PGE2 is the opposite enantiomer of PGE2. Significant amounts of racemic PGE2 (rac-PGE2) are generated in vitro and in vivo in settings of oxidative stress via the isoprostane pathway. A proposed mechanism for the formation of rac-PGE2 involves the base catalyzed equilibration from 15-E2t-isoprostane (8-iso-PGE2), generated from the 15-H2t-isoprostane endoperoxide.1
This information has been provided by Cayman Chemical
References
1. Gao, L., Zackert, W.E., Hasford, J.J., et al. Formation of prostaglandin E2 and prostaglandin D2 via the isoprostane pathway: A mechanism for the generation of bioactive prostaglandins independent of the cyclooxygenase. The Journal of Biological Chemisty 278(31), 28479-28489 (2003).
References
String Representations
InChiKey (Click to copy)
XEYBRNLFEZDVAW-OBUVHCMGSA-N
InChi (Click to copy)
InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/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]1C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
0
Rotatable Bonds
12
Van der Waals Molecular Volume
375.59
Topological Polar Surface Area
94.83
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.82
Molar Refractivity
98.17
Admin
Created at
-
Updated at
22nd Mar 2022