15-Deoxy-delta-12,14-prostaglandin J2 2-glycerol ester (CHEM041412)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:28:24 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041412
Identification
Common Name15-Deoxy-delta-12,14-prostaglandin J2 2-glycerol ester
ClassSmall Molecule
Description15-deoxy-Δ12,14-Prostaglandin J2-2-glycerol ester (15-deoxy-Δ12,14-PGJ2-2-glycerol ester) is formed from PGD2 by the elimination of two molecules of water. It binds selectively to PPARγ with an EC50 value of 2 ¬µM in a murine chimera system.1,2 15-deoxy-Δ12,14-PGJ2-2-glycerol ester is more potent than PGD2, Δ12-PGJ2, and PGJ2 in stimulating lipogenesis in C3H10T1/2 cells. The EC50 value for induction of adipocyte differentiation in cultured fibroblasts is 7 ¬µM.1 PG glycerol esters are generated by the action of cyclooxygenase-2 on the endocannabinoid 2-arachidonyl glycerol.3 The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. While the stability and metabolism of these PG products has been investigated,4 little is known about their intrinsic biological activity.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
15-Deoxy-δ12,14-prostaglandin J2-2-glycerol esterGenerator
15-Deoxy-Delta12,14-PGJ2-2-glycerol esterHMDB
15-Deoxy-Δ12,14-PGJ2-2-glycerol esterHMDB
1,3-Dihydroxypropan-2-yl (5Z)-7-[(1S,5E)-5-[(2Z)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acidGenerator
15-Deoxy-δ-12,14-prostaglandin J2 2-glycerol esterGenerator
Chemical FormulaC23H34O5
Average Molecular Mass390.513 g/mol
Monoisotopic Mass390.241 g/mol
CAS Registry NumberNot Available
IUPAC Name1,3-dihydroxypropan-2-yl (5Z)-7-[(1S,5E)-5-[(2Z)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoate
Traditional Name1,3-dihydroxypropan-2-yl (5Z)-7-[(1S,5E)-5-[(2Z)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoate
SMILESCCCCC\C=C/C=C1/C(=O)C=C[C@@H]1C\C=C/CCCC(=O)OC(CO)CO
InChI IdentifierInChI=1S/C23H34O5/c1-2-3-4-5-6-10-13-21-19(15-16-22(21)26)12-9-7-8-11-14-23(27)28-20(17-24)18-25/h6-7,9-10,13,15-16,19-20,24-25H,2-5,8,11-12,14,17-18H2,1H3/b9-7-,10-6-,21-13+/t19-/m0/s1
InChI KeyJGKIBUMNHSZUSL-WZOKZYBXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • 2-acyl-sn-glycerol
  • Monoradylglycerol
  • Monoacylglycerol
  • Fatty acid ester
  • Glycerolipid
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.44ALOGPS
logP4.28ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.28ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity115.47 m³·mol⁻¹ChemAxon
Polarizability45.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fy7-4290000000-2e69e5cdc497a458526cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-e682f2d0eee7508233faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4o-0009900000-d9014243671eca434311Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a66-0009400000-52a6d904e709d50b9814Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9022000000-ecb40ff43106a6dd5326Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ar1-7096000000-73c4542679ff99a1b0dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052s-2191000000-94610eb4de642b69be89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-36e96f08f75544b0768eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-36e96f08f75544b0768eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btr-0009300000-eedb6dbe84c240f523b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-de76cf918d8bf40a2145Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014o-0009000000-b85a37801eb89dc18d31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-0009000000-b6b7e355a2d934e4db4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-d8c2cad3b1e5f442cc4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-0009600000-23e07400f40cad95a396Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001o-0009000000-07794ae3f7f0e1351f30Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013656
FooDB IDFDB029626
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776718
ChEBI ID172626
PubChem Compound ID53481918
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM