LIPID MAPS

Structure Database (LMSD)

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Common Name

PGE2-d9

Systematic Name

9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic-17,17,18,18,19,19,20,20,20-d9 acid

Synonyms

Prostaglandin E2-d9
Dinoprostone-d9
Prostin E2-d9
9-oxo-11alpha,15S-dihydroxy-prosta-5Z,13E-dien-1-oic-17,17,18,18,19,19,20,20,20-d9 acid

LM ID

LMFA03010257

Formula

C₂₀H₂₃D₉O₅

Exact Mass

Calculate m/z

361.281466

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Prostaglandin E2-d9 (PGE2-d9) is intended for use as an internal standard for the quantification of PGE2 by GC- or LC-MS. 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 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. 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).

2. 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).

3. 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).

4. 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).

5. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

XEYBRNLFEZDVAW-GMIZMOFXSA-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/i1D3,2D2,3D2,6D2

SMILES (Click to copy)

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