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Showing Compound Prostaglandin PGE2 glyceryl ester (FDB029268)

Record Information
Version1.0
Creation date2011-09-21 01:52:53 UTC
Update date2017-04-03 04:56:44 UTC
Primary IDFDB029268
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProstaglandin PGE2 glyceryl ester
DescriptionGE2 glycerol ester is a COX-2 oxidative metabolite of 2-arachidonoyl glycerol, modulates inhibitory synaptic transmission in mouse hippocampal neurons 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain,1 and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.2 Incubation of 2-AG with COX-2 and specific prostaglandin H2 (PGH2) isomerases in cell cultures and isolated enzyme preparations results in prostaglandin glycerol ester formation.3 The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 2:1-glyceryl ester mixture in typical aqueous media. While the stability and metabolism of these prostaglandin products has been investigated,4 little is known about their intrinsic biological activity. Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB]
CAS Number122-60-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.24ALOGPS
logP2.05ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.13ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity116.46 m³·mol⁻¹ChemAxon
Polarizability48.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H38O7
IUPAC name1,3-dihydroxypropan-2-yl (5Z)-7-[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoate
InChI IdentifierInChI=1S/C23H38O7/c1-2-3-6-9-17(26)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-18(15-24)16-25/h4,7,12-13,17-20,22,24-26,28H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,19-,20-,22-/m0/s1
InChI KeyHJWDPZIOTMUWRW-KSGZNQJUSA-N
Isomeric SMILESCCCCC[C@H](O)\C=C\[C@@H]1[C@@H](O)CC(=O)[C@H]1C\C=C/CCCC(=O)OC(CO)CO
Average Molecular Weight426.5436
Monoisotopic Molecular Weight426.26175357
Classification
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
  • Fatty alcohol
  • 2-acyl-sn-glycerol
  • Monoradylglycerol
  • Monoacylglycerol
  • Glycerolipid
  • Fatty acid ester
  • Cyclopentanol
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSProstaglandin PGE2 glyceryl ester, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f92-3910314000-41ffb0d63d9fa81c4012Spectrum
Predicted GC-MSProstaglandin PGE2 glyceryl ester, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-a7b6ab3f50632d2b03022017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004o-0000900000-8f81a006abf4416a6c192017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00i6-0004900000-78319990ea836f29b8f22017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000900000-5aee52a8803fc54aa10d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ui0-0009700000-e5c4ac42d72357fbf3362021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg0-0009400000-8e50f84ce6817d11d5e52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-1739061e56a734cbd42a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000900000-1739061e56a734cbd42a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004p-0009300000-c085980c864ed35c8e0b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-8059300000-b81232d90d1ece32d2db2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-4029000000-de3fe71b922ced904b382021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k92-2293000000-a350405088835b0f55f32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-5e14ba638d737caacdb62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0000900000-663ea5794e1fb3a9283b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00i0-0007900000-22b4c476a7d75f31fdb12021-09-25View Spectrum
NMRNot Available
ChemSpider ID30776688
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481593
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13045
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference