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Showing Compound Prostaglandin E2 (FDB022498)

Record Information
Version1.0
Creation date2011-09-21 00:14:56 UTC
Update date2019-11-26 03:21:03 UTC
Primary IDFDB022498
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProstaglandin E2
DescriptionDinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, induction of uterine contractions and of platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535) Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535) 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]. Prostaglandin E2 is found in many foods, some of which are common sage, nanking cherry, colorado pinyon, and sweet basil.
CAS Number363-24-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(-)-Prostaglandin E2hmdb
(15S)-Prostaglandin e2ChEBI
(5Z,11a,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11a,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidChEBI
(5Z,11α,13e,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11α,13e,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoatehmdb
(5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoic acidhmdb
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoateGenerator
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoateGenerator
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoatehmdb
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acidhmdb
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoatehmdb
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acidhmdb
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoateGenerator
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dienoateGenerator
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoateGenerator
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acidChEBI
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoateGenerator
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acidChEBI
5-trans-PGE2hmdb
DinoprostonChEBI
DinoprostonaChEBI
Dinoprostonehmdb
Dinoprostonumhmdb
Glandinhmdb
l-Prostaglandin E2hmdb
Minprositin E2hmdb
Minprostin E2hmdb
PGE2hmdb
Prepidilhmdb
PropessChEBI
Prostaglandin Ehmdb
Prostaglandin E2hmdb
Prostaglandin E2alphahmdb
Prostarmon Ehmdb
Prostinhmdb
Prostin E2hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP3.31ALOGPS
logP3.23ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.44 m³·mol⁻¹ChemAxon
Polarizability40.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O5
IUPAC name7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
InChI IdentifierInChI=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)/t15-,16+,17+,19+/m0/s1
InChI KeyXEYBRNLFEZDVAW-DODZYUBVSA-N
Isomeric SMILES[H]C(=C[C@@]1([H])[C@]([H])(O)CC(=O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
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
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4444059
ChEMBL IDCHEMBL548
KEGG Compound IDC00584
Pubchem Compound ID5280360
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00917
HMDB IDHMDB01220
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35424
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDinoprostone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Prostaglandin E synthasePTGESO14684
Prostaglandin E2 receptor EP4 subtypePTGER4P35408
Carbonyl reductase [NADPH] 1CBR1P16152
Carbonyl reductase [NADPH] 3CBR3O75828
Prostaglandin E synthase 2PTGES2Q9H7Z7
Prostaglandin E synthase 3PTGES3Q15185
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference