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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:02 UTC
Update Date2019-01-11 19:17:10 UTC
HMDB IDHMDB0002664
Secondary Accession Numbers
  • HMDB02664
Metabolite Identification
Common NameProstaglandin E3
DescriptionProstaglandin E3 is from the cyclooxygenase metabolism of eicosapentaenoic acid.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.
Structure
Data?1547234230
Synonyms
ValueSource
(5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acidChEBI
9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoic acidChEBI
PGE3ChEBI
(5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acidGenerator
(5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acidGenerator
9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoateGenerator
(-)-Prostaglandin e3HMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoateHMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acidHMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acid stereoisomerHMDB
delta(17)-PGE1HMDB
delta(17)-Prostaglandin e1HMDB
Prostaglandin e3MeSH
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
Traditional Name(-)-prostaglandin E3
CAS Registry Number802-31-3
SMILES
CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O5/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/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChI KeyCBOMORHDRONZRN-QLOYDKTKSA-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
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP2.88ALOGPS
logP2.86ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity100.55 m³·mol⁻¹ChemAxon
Polarizability39.44 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-7496000000-9210fb4674d794816bc0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-9101680000-a66ceba0ca4003a25001JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0019000000-3a37659687433065f9daJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-4197000000-5a2017a0bfe4592e8fffJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9220000000-feedd008762c81af1d13JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0009000000-50f3213aa3eff0d0faf7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-2149000000-29aed26fd57d9c5f3bc8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9431000000-5c1e13cc53c44b8f766dJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023042
KNApSAcK IDNot Available
Chemspider ID4444439
KEGG Compound IDC06439
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProstaglandin E3
METLIN ID3494
PubChem Compound5280937
PDB IDNot Available
ChEBI ID28031
References
Synthesis ReferenceOkamoto, Sentaro; Kobayashi, Yuichi; Sato, Fumie. A highly efficient synthesis of natural PGE3 and 5,6-dihydro PGE3 via two-component coupling process. Tetrahedron Letters (1989), 30(33), 4379-82.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kivits GA, Nugteren DH: The urinary excretion of prostaglandins E and their corresponding tetranor metabolites by rats fed a diet rich in eicosapentaenoate. Biochim Biophys Acta. 1988 Feb 4;958(2):289-99. [PubMed:2827784 ]
  2. Fischer S, von Schacky C, Schweer H: Prostaglandins E3 and F3 alpha are excreted in human urine after ingestion of n - 3 polyunsaturated fatty acids. Biochim Biophys Acta. 1988 Dec 16;963(3):501-8. [PubMed:3196747 ]