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Structure Database (LMSD)

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Common Name

Unoprostone

Systematic Name

9,11-dihydroxy-15-oxo-20a,20b-dihomoprost-5Z-en-1-oic acid

Synonyms

(+)-(Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-5-heptenoic acid
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid
13,14-dihydro-15-keto-20-ethyl PGF2alpha
Unoprostone

LM ID

LMFA03010204

Formula

C₂₂H₃₈O₅

Exact Mass

Calculate m/z

382.271926

Sum Composition

FA 22:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Unoprostone is an agonist of FP receptors (EC50 = 4.12 µM), an active metabolite the ocular hypotensive agent unoprostone isopropyl ester , and a derivative of prostaglandin F2α (PGF2α).¹ It is formed from unoprostone isopropyl ester by hydrolysis. Intravitreal administered unoprostone (1.2, 3.6, or 6 µg/µl) prevents constant light-induced degradation of photoreceptors in rats.²

This information has been provided by Cayman Chemical

References

1. Sharif, N.A., Kelly, C.R., Crider, J.Y., et al. Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J. Ocul. Pharmacol. Ther. 19(6), 501-515 (2003).

2. Hayami , K., and Unoki, K. Photoreceptor protection against constant light-induced damage by isopropyl unoprostone, a prostaglandin F2α metabolite-related compound. Ophthalmic Res. 33(4), 203-209 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells.,
J Ocul Pharmacol Ther, 2003

Pubmed ID: 14733708

String Representations

InChiKey (Click to copy)

TVHAZVBUYQMHBC-SNHXEXRGSA-N

InChi (Click to copy)

InChI=1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,18-21,24-25H,2-5,7-8,10-16H2,1H3,(H,26,27)/b9-6-/t18-,19-,20+,21-/m1/s1

SMILES (Click to copy)

[C@@H]1([C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O)CCC(=O)CCCCCCC