Structure Database (LMSD)

Common Name
20-ethyl-PGE2
Systematic Name
20a,20b-dihomo-9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic acid
Synonyms
  • 20-ethyl-Prostaglandin E2
LM ID
LMFA03010174
Formula
Exact Mass
Calculate m/z
380.256275
Sum Composition
Status
Curated

Classification

Biological Context

20-ethyl Prostaglandin E2 (20-ethyl PGE2) is an analog of PGE2 in which the ω-chain has been extended by the addition of two methylene carbon atoms. The only well studied prostaglandin analog with this structural feature is unoprostone, an F-series prostaglandin that is clinically approved as a glaucoma medication.1 Unoprostone also contains lower side chain modifications (13,14-dihydro-15-keto) which severely limit its affinity for FP receptors, contributing to its lack of potency as a medication. 20-ethyl PGE2 retains the natural 15(S) allylic hydroxyl in the lower side chain, which may improve its potency relative to unoprostone. However, ligand binding assays of this analog with respect to EP or other prostanoid receptors have not been published. E-type prostaglandins have been widely reported to have inflammatory, cytoprotective, and a variety of other effects.2,3,4

This information has been provided by Cayman Chemical

References

1. Jackson, G.M., Sharp, H.T., and Varner, M.W. Cervical ripening before induction of labor: A randomized trial of prostaglandin E2 gel versus low-dose oxytocin. Am. J. Obstet. Gynecol. 171(4), 1092-1096 (1994).
4. Haria, M., and Spencer, C.M. Unoprostone (isopropyl unoprostone). Drugs Aging 9(3), 213-218 (1996).

String Representations

InChiKey (Click to copy)
NXMMZTNQIJBMBC-QKIVIXBWSA-N
InChi (Click to copy)
InChI=1S/C22H36O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,14-15,17-19,21,23,25H,2-5,7-8,10-13,16H2,1H3,(H,26,27)/b9-6-,15-14+/t17-,18+,19+,21+/m0/s1
SMILES (Click to copy)
C(CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCCCC)[C@H](O)CC1=O)(=O)O

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 410.19
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 4.60
Molar Refractivity 107.40

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Updated at
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