Structure Database (LMSD)

OH HO O OH O
Common Name
16-phenyl-tetranor-PGE2
Systematic Name
9-oxo-11R,15S-dihydroxy-16-phenyl-17,18,19,20-tetranor-5Z,13E-prostadienoic acid
Synonyms
  • 16-phenyl-tetranor-Prostaglandin E2
LM ID
LMFA03010066
Formula
C22H28O5
Exact Mass
Calculate m/z
372.193675
Sum Composition
FA 22:8;O3
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

String Representations

InChiKey (Click to copy)
DXWJXQSQVUJRNS-YYWARMNLSA-N
InChi (Click to copy)
InChI=1S/C22H28O5/c23-17(14-16-8-4-3-5-9-16)12-13-19-18(20(24)15-21(19)25)10-6-1-2-7-11-22(26)27/h1,3-6,8-9,12-13,17-19,21,23,25H,2,7,10-11,14-15H2,(H,26,27)/b6-1-,13-12+/t17-,18-,19-,21-/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CC2C=CC=CC=2)[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Structure activity studies leading to a tissue-selective hypotensive prostaglandin analog, 13,14-dihydro-16-phenyl-omega-tetranor PGE2.,
Prostaglandins, 1980
Pubmed ID: 7422897

Other Databases

CHEBI ID
165308
LIPIDBANK ID
XPR1748
PubChem CID
5283067

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 2
Aromatic Rings 1
Rotatable Bonds 10
Van der Waals Molecular Volume 379.01
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 3.49
Molar Refractivity 104.17

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Created at
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Updated at
5th Apr 2022