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Structure Database (LMSD)

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Common Name

PGE2-d4

Systematic Name

11R,15S-dihydroxy-9-oxo-5Z,13E-prostadienoic acid (3,3,4,4-d4)

Synonyms

Prostaglandin E2-d4

LM ID

LMFA03010008

Formula

C₂₀H₂₈D₄O₅

Exact Mass

Calculate m/z

356.250083

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Prostaglandin E2-d4 (PGE2-d4) contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of PGE2 by GC- or LC-mass spectrometry. PGE2 is one of the primary cyclooxygenase products of arachidonic acid and one of the most widely investigated prostaglandins. Its activity influences inflammation, fertility and parturition, gastric mucosal integrity, and immune modulation.^1,2,3,4 The effects of PGE2 are transduced by at least four distinct receptors designated EP1, EP2, EP3, and EP4.5 The affinity constants (Kd) of PGE2 for these receptors range from 1-10 nM depending on the receptor subtype and tissue.

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. Arvind, P., Papavassiliou, E.D., Tsioulias, G.J., et al. Prostaglandin E2 down-regulates the expression of HLA-DR antigen in human colon adenocarcinoma cell lines. Biochemistry 34(16), 5604-5609 (1995).

3. Coleman, R.A., Smith, W.L., and Narumiya, S. International Union of Pharmacology classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol. Rev. 46(2), 205-229 (1994).

4. Jackson, G.M., Sharp, H.T., and Varner, M.W. Cervical ripening before induction of labor: A randomized trial of prostaglandin E2 gel versus low-dose oxytocin. Am. J. Obstet. Gynecol. 171(4), 1092-1096 (1994).

5. Willis, A.L., and Cornelsen, M. Repeated injection of prostaglandin E2 in rat paws induces chronic swelling and a marked decrease in pain threshold. Prostaglandins 3(3), 353-357 (1973).

References

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

XEYBRNLFEZDVAW-YOLMOHOWSA-N

InChi (Click to copy)

InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1/i5D2,8D2

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1C/C=C\C([2H])([2H])C([2H])([2H])CC(=O)O