Structure Database (LMSD)

Common Name
PGF2alpha methyl ether
Systematic Name
1-methoxy-9S,11R,15S-trihydroxy-5Z,13E-prostadiene
Synonyms
  • Prostaglandin F2alpha methyl ether
LM ID
LMFA03010073
Formula
C21H38O4
Exact Mass
Calculate m/z
354.27701
Sum Composition
FA 21:2;O2
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

Prostaglandin F2α alcohol methyl ether (PGF2α-OMe) is an analog of PGF2α in which the C-1 carboxyl group has been replaced an O-methyl ether. The compound is reported to retain ocular hypotensive properties, but the receptors which mediate this activity have not been clearly documented.1,2

This information has been provided by Cayman Chemical

References

1. Woodward, D.F., and Chan, M.F. Preparation of PGF-1 alcohols as ocular hypotensives. 38204, 1-12 (1993).
2. Woodward, D.F., Krauss, A.H.P., Chen, J., et al. Replacement of the carboxylic acid group of prostaglandin F2α with a hydroxyl or methoxy substituent provides biologically unique compounds. Br. J. Pharmacol. 130(8), 1933-1943 (2000).

String Representations

InChiKey (Click to copy)
VWEVSUSNDAHANL-GPPPFWBLSA-N
InChi (Click to copy)
InChI=1S/C21H38O4/c1-3-4-8-11-17(22)13-14-19-18(20(23)16-21(19)24)12-9-6-5-7-10-15-25-2/h6,9,13-14,17-24H,3-5,7-8,10-12,15-16H2,1-2H3/b9-6-,14-13+/t17-,18+,19+,20-,21+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCCOC

Other Databases

CHEBI ID
137215
LIPIDBANK ID
XPR1755
PubChem CID
5283074
Cayman ID
16014

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 389.38
Topological Polar Surface Area 69.92
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 4.75
Molar Refractivity 104.41

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Updated at
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