Structure Database (LMSD)

Common Name
PGB3
Systematic Name
9-oxo-15S-hydroxy-5Z,8(12),13E,17Z-prostatetraenoic acid
Synonyms
  • Prostaglandin B3
LM ID
LMFA03010141
Formula
C20H28O4
Exact Mass
Calculate m/z
332.19876
Sum Composition
FA 20:6;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

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

Biological Context

Prostaglandin B3 (PGB3) is a non-enzymatic dehydration product resulting from the treatment of Prostaglandin E3 (PGE3) with strong base. In a structure-activity binding study to determine the affinity of various prostaglandins to human PPARγ, PGB3 exhibited a Ki value greater than 1 mM.1 In contrast, PGB1 and PGB2 showed significantly higher affinity for PPARγ, with Ki values of 26 and 77 µM, respectively, the same assay.

This information has been provided by Cayman Chemical

References

1. Ferry, G., Bruneau, V., Beauverger, P., et al. Binding of prostaglandins to human PPARγ: Tool assessment and new natural ligands. Eur. J. Pharmacol. 417(1-2), 77-89 (2001).

String Representations

InChiKey (Click to copy)
DQRGQQAJYRBDRP-UNBCGXALSA-N
InChi (Click to copy)
InChI=1S/C20H28O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h3-4,6-7,12,14,17,21H,2,5,8-11,13,15H2,1H3,(H,23,24)/b6-3-,7-4-,14-12+/t17-/m0/s1
SMILES (Click to copy)
C1(/C=C/[C@@H](O)C/C=C\CC)CCC(=O)C=1C/C=C\CCCC(=O)O

Other Databases

CHEBI ID
134511
LIPIDBANK ID
XPR1703
PubChem CID
5283113
Cayman ID
11990

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 361.52
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 4.41
Molar Refractivity 96.22

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Updated at
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