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Structure Database (LMSD)

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Common Name

9-deoxy-9-methylene-PGE2

Systematic Name

9-methylene-11R,15S-dihydroxy-5Z,13E-prostadienoic acid

Synonyms

9-deoxy-9-methylene-Prostaglandin E2

LM ID

LMFA03010058

Formula

C₂₁H₃₄O₄

Exact Mass

Calculate m/z

350.24571

Sum Composition

FA 21:4;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

9-deoxy-9-methylene Prostaglandin E2 (9-deoxy-9-methylene PGE2) is a stable, isosteric analog of PGE2 . 9-deoxy-9-methylene PGE2 retains the biological profile of PGE2 with fewer side effects. In the rat 9-deoxy-9-methylene PGE2 is equipotent to PGE2 in decreasing blood pressure. It also stimulates the gerbil colon and primate uterus at the same potency as PGE2.1

This information has been provided by Cayman Chemical

References

1. Bundy, G.L., Kimball, F.A., Robert, A., et al. Synthesis and biological activity of 9-deoxo-9-methylene and related prostaglandins. Adv. Prostaglandin Thromboxane Res. 6, 355-363 (1980).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthesis and biological activity of 9-deoxo-9-methylene and related prostaglandins.,
Adv Prostaglandin Thromboxane Res, 1980

Pubmed ID: 7386275

String Representations

InChiKey (Click to copy)

VKEJXDXJUFQESA-DLMPNJEASA-N

InChi (Click to copy)

InChI=1S/C21H34O4/c1-3-4-7-10-17(22)13-14-19-18(16(2)15-20(19)23)11-8-5-6-9-12-21(24)25/h5,8,13-14,17-20,22-23H,2-4,6-7,9-12,15H2,1H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19+,20+/m0/s1

SMILES (Click to copy)

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