LIPID MAPS

Structure Database (LMSD)

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Common Name

PGE2-EA

Systematic Name

N-(11R,15S-dihydroxy-9-oxo-5Z,13E-prostadienoyl)-ethanolamine

Synonyms

Prostaglandin E2-EA
Prostamide-E2
PME2

LM ID

LMFA03010151

Formula

C₂₂H₃₇NO₅

Exact Mass

Calculate m/z

395.267174

Sum Composition

NAE 20:4;O3

Status

Active

Show lipids differing only in stereochemistry/bond geometry

Classification

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2.,
J Biol Chem, 1997

Pubmed ID: 9261124

String Representations

InChiKey (Click to copy)

GKKWUSPPIQURFM-IGDGGSTLSA-N

InChi (Click to copy)

InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-19,21,24-25,27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,21+/m0/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)NCCO

Other Databases

CHEBI ID

138793

PubChem CID

5283119

Cayman ID

14012

Calculated Physicochemical Properties

Heavy Atoms 28

Rings 1

Aromatic Rings 0

Rotatable Bonds 14

Van der Waals Molecular Volume 421.19

Topological Polar Surface Area 106.86

Hydrogen Bond Donors 4

Hydrogen Bond Acceptors 6

logP 3.42

Molar Refractivity 111.61

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Created at

Updated at

22nd Sep 2023