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Structure Database (LMSD)

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Common Name

PGE1 alcohol

Systematic Name

1,11R,15S-trihydroxy-13E-prosten-9-one

Synonyms

Prostaglandin E1 alcohol

LM ID

LMFA03010053

Formula

C₂₀H₃₆O₄

Exact Mass

Calculate m/z

340.26136

Sum Composition

FA 20:2;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Prostaglandin E1 (PGE1) alcohol is a non-irritant bronchodilator, with relaxant activity on the human bronchial muscle in vitro, comparable to PGE1 at concentrations of 0.01 to 10.0 µg/ml.^1,2 Asthmatics receiving single dose inhalation treatments reported significant but short-acting bronchodilation at doses of 10 and 30 µg.¹ PGE1 alcohol binds to the mouse recombinant EP3 and EP4 receptors with Ki values of 330 and 190 nM, respectively.³

This information has been provided by Cayman Chemical

References

1. Kiriyama, M., Ushikubi, F., Kobayashi, T., et al. Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br. J. Pharmacol. 122(2), 217-224 (1997).

2. Gardiner, P.J., Copas, J.L., Schneider, C., et al. 2-Decarboxy-2-hydroxymethyl prostaglandin E1 (TR4161), a prostaglandin bronchodilator of low tracheobronchial irritancy. Prostaglandins 19(3), 349-370 (1980).

3. Nizankowska, E., Sheridan, A.Q., Maile, M.H., et al. Bronchodilatory properties of 2-decarboxy-2-hydroxymethyl prostaglandin E1. Prostaglandins 29(3), 349-362 (1985).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Bronchodilatory properties of 2-decarboxy-2-hydroxymethyl prostaglandin E1.,
Prostaglandins, 1985

Pubmed ID: 3858912

String Representations

InChiKey (Click to copy)

CMHCOGHTKXUQKW-KOAZGICHSA-N

InChi (Click to copy)

InChI=1S/C20H36O4/c1-2-3-7-10-16(22)12-13-18-17(19(23)15-20(18)24)11-8-5-4-6-9-14-21/h12-13,16-18,20-22,24H,2-11,14-15H2,1H3/b13-12+/t16-,17+,18+,20+/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1CCCCCCCO