Structure Database (LMSD)

Common Name
PGE3
Systematic Name
9-oxo-11R,15S-dihydroxy-5Z,13E,17Z-prostatrienoic acid
Synonyms
  • Prostaglandin E3
LM ID
LMFA03010135
Formula
C20H30O5
Exact Mass
Calculate m/z
350.209325
Sum Composition
FA 20:5;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

Prostaglandin E3 (PGE3) is formed via the cyclooxygenase (COX) metabolism of eicosapentaenoic acid.1 In human ocular tissue, it comprises 2.4% of the COX products formed.1 When applied to the eyes of a rabbit, a 1 µg dose of PGE3 decreases intraocular pressure from 21 mmHg to about 17 mmHg.2

This information has been provided by Cayman Chemical

References

1. Kulkarni, P.S., and Srinivasan, B.D. Prostaglandins E3 and D3 lower intraocular pressure. Invest. Ophthalmol. Vis. Sci. 26(8), 1178-1182 (1985).
2. Kulkarni, P.S., and Srinivasan, B.D. Eicosapentaenoic acid metabolism in human and rabbit anterior uvea. Prostaglandins 31(6), 1159-1164 (1986).

String Representations

InChiKey (Click to copy)
CBOMORHDRONZRN-QLOYDKTKSA-N
InChi (Click to copy)
InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)C/C=C\CC)[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O

Other Databases

KEGG ID
C06439
HMDB ID
HMDB0002664
CHEBI ID
28031
LIPIDBANK ID
XPR1402
PubChem CID
5280937
Cayman ID
14990

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 372.95
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 3.60
Molar Refractivity 98.07

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Updated at
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