Structure Database (LMSD)

Common Name
11beta-PGE2
Systematic Name
9-oxo-11S,15S-dihydroxy-5Z,13E-prostadienoic acid
Synonyms
  • 11beta-Prostaglandin E2
  • 11beta-PGE2
  • ent-8,15-diepi-15-E2c-IsoP
  • 9-oxo-11S,15S-dihydroxy-5Z,13E-prostadienoic acid-cyclo[8R,12R]
LM ID
LMFA03010060
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

11β-PGE2 is the C-11 epimer of PGE2. It is a moderate inhibitor of PGE2 binding to rat hypothalamic membranes with a Ki value of 53 nM.1 11β-PGE2 also stimulates bone resorption in rats at concentrations of 10 to 1,000 nM which is similar to PGE2.2 11β-PGE2 inhibits PGE2 binding to the prostaglandin transporter protein with a Ki of 56 nM.3

This information has been provided by Cayman Chemical

References

1. Itoh, S., Lu, R., Bao, Y., et al. Structural determinants of substrates for the prostaglandin transporter PGT. Mol. Pharmacol. 50, 736-742 (1996).
2. Raisz, L.G., and Woodiel, F.N. Effect of alterations in the cyclopentane ring on bone resorptive activity of prostaglandin. Prostaglandins 37, 229-235 (1989).
3. Dray, F., and Heaulme, M. Prostaglandins of the E series inhibit release of noradrenaline in rat hypothalamus by a mechanism unrelated to classical α2 adrenergic presynaptic inhibition. Neuropharmacology 23, 457-462 (1984).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
XEYBRNLFEZDVAW-YUOXZBOXSA-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

HMDB ID
HMDB0060041
CHEBI ID
140932
LIPIDBANK ID
XPR1742
PubChem CID
5283061
Cayman ID
14510

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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