Structure Database (LMSD)

Common Name
5-trans-PGE2
Systematic Name
9-oxo-11R,15S-dihydroxy-5E,13E-prostadienoic acid
Synonyms
  • 5-trans-Prostaglandin E2
LM ID
LMFA03010148
Formula
C20H32O5
Exact Mass
Calculate m/z
352.224975
Sum Composition
FA 20:4;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

Biological Context

5-trans PGE2 occurs naturally in some gorgonian corals and is a common impurity in commercial lots of PGE1.1 It is 18 times more potent than PGE2 in activating adenylate cyclase in NCB-20 cell homogenates.2 5-trans PGE2 accelerates fibrinolysis by enhancing plasminogen activation mediated by tissue-type plasminogen activator.3 It also inhibits platelet aggregation in human PRP with an IC50 of 180 nM.4

This information has been provided by Cayman Chemical

References

1. Bundy, G.L., Schneider, W.P., Lincoln, F.H., et al. Isolation of a new naturally occurring prostaglandin, 5-trans-PGA2. Synthesis of 5-trans-PGE2 and 5-trans-PGF2α. J. Am. Chem. Soc. 94(6), 2124 (1972).
2. Hensby, C.N., and MacDermot, J. Structure-activity relationships of prostanoids that activate adenylate cyclase of neuronal hybrid cells. Biochem. Soc. Trans. 7(6), 1302-1304 (1979).
3. Shimokawa, M., Urano, T., and Kinoshita, T. trans-5-Prostaglandin E2 stimulates plasminogen activation by tissue-type plasminogen activator. Biochim. Biophys. Acta 1137(3), 317-320 (1992).
4. Kobzar, G., Mardla, V., Järving, I., et al. Comparison of the inhibitory effect of E-prostaglandins in human and rabbit platelet-rich plasma and washed platelets. Comp. Biochem. Physiol. 106(2), 489-494 (1993).

String Representations

InChiKey (Click to copy)
XEYBRNLFEZDVAW-BRNHSORCSA-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
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1C/C=C/CCCC(=O)O

Other Databases

LIPIDBANK ID
XPR1711
PubChem CID
5283116
Cayman ID
14210

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 375.59
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 3.82
Molar Refractivity 98.17

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Updated at
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