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Structure Database (LMSD)

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Common Name

15-methyl-15S-PGE2

Systematic Name

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

Synonyms

15-methyl-15S-Prostaglandin E2

LM ID

LMFA03010064

Formula

C₂₁H₃₄O₅

Exact Mass

Calculate m/z

366.240625

Sum Composition

FA 21:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15(S)-15-methyl Prostaglandin E2 (15(S)-15-methyl PGE2) is a potent, metabolically stable analog of PGE2. It is a potent gastric antisecretory and antiulcer compound.¹ 15(S)-15-methyl PGE2 binds to human myometrium with twice the affinity of PGE2 and is ten times more potent than PGE1 in contracting uterine smooth muscle.²

This information has been provided by Cayman Chemical

References

1. Robert, A., Schultz, J.R., Nezamis, J.E., et al. Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16,16-dimethyl PGE2. Intravenous, oral and intrajejunal administration. Gastroenterology 70(3), 359-370 (1976).

2. Kimball, F.A., Kirton, K.T., Spilman, C.H., et al. Prostaglandin E1 specific binding in human myometrium. Biol. Reprod. 13(4), 482-489 (1975).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Total synthesis of 15-methylprostaglandins,
J Am Chem Soc, 1974

DOI: 10.1021/ja00825a027

String Representations

InChiKey (Click to copy)

XSGQFHNPNWBVPT-DSFPJDRCSA-N

InChi (Click to copy)

InChI=1S/C21H34O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-17,19,23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,19-,21+/m1/s1

SMILES (Click to copy)

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