Structure Database (LMSD)

Common Name
16,16-dimethyl-PGE1
Systematic Name
9-oxo-11R,15S-dihydroxy-16,16-dimethyl-13E-prostaenoic acid
Synonyms
  • 16,16-dimethyl-Prostaglandin E1
LM ID
LMFA03010057
Formula
C22H38O5
Exact Mass
Calculate m/z
382.271925
Sum Composition
FA 22:3;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

16,16-dimethyl PGE1 is a metabolically stable synthetic analog of PGE1. It induces human vascular smooth muscle contractions in vitro. It is 2, 3, and 6 times more potent than PGF2α in contracting tracheal, bronchial, and bronchiolar smooth muscle, respectively.1

This information has been provided by Cayman Chemical

References

1. Karim, S.M.M., Adaikan, P.G., and Kottegoda, S.R. Prostaglandins and human respiratory tract smooth muscle: Structure activity relationship. Adv. Prostaglandin Thromboxane Res. 7, 969-980 (1980).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Prostaglandins and human respiratory tract smooth muscle: structure activity relationship.,
Adv Prostaglandin Thromboxane Res, 1980
Pubmed ID: 7369062

String Representations

InChiKey (Click to copy)
RQOFITYRYPQNLL-ZWSAOQBFSA-N
InChi (Click to copy)
InChI=1S/C22H38O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h12-13,16-17,19-20,24-25H,4-11,14-15H2,1-3H3,(H,26,27)/b13-12+/t16-,17-,19-,20-/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)C(C)(C)CCCC)[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O

Other Databases

CHEBI ID
186965
LIPIDBANK ID
XPR1739
PubChem CID
5283058
Cayman ID
13750

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 412.83
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 4.68
Molar Refractivity 107.43

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Updated at
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