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Human Metabolome Database Version 3.5

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Showing metabocard for Prostaglandin E3 (HMDB02664)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:02 -0600
Update Date 2013-02-08 17:12:02 -0700
HMDB ID HMDB02664
Secondary Accession Numbers None
Metabolite Identification
Common Name Prostaglandin E3
Description Prostaglandin 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-prostaglandin E3
  2. 7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-Heptenoate
  3. 7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-Heptenoic acid
  4. 7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-Heptenoic acid stereoisomer
  5. PGE3
  6. Prostaglandin E3
Chemical Formula C20H30O5
Average Molecular Weight 350.4492
Monoisotopic Molecular Weight 350.20932407
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 IUPAC Name prostaglandin E3
CAS Registry Number 802-31-3
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 Key CBOMORHDRONZRN-QLOYDKTKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Prostaglandins and related compounds
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Cyclic Alcohol
  • Ketone
  • Secondary Alcohol
Direct Parent Prostaglandins and related compounds
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.088 g/L ALOGPS
LogP 2.88 ALOGPS
LogP 2.86 ChemAxon
LogS -3.60 ALOGPS
pKa (strongest acidic) 4.3 ChemAxon
pKa (strongest basic) -1.7 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 11 ChemAxon
Refractivity 100.55 ChemAxon
Polarizability 39.44 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
<0.1 uM Adult (>18 years old) Not Specified Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023042
KNApSAcK ID Not Available
Chemspider ID 4444439 Link_out
KEGG Compound ID C06439 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02664 Link_out
Metagene Link HMDB02664 Link_out
METLIN ID 3494 Link_out
PubChem Compound 5280937 Link_out
PDB ID Not Available
ChEBI ID 28031 Link_out
References
Synthesis Reference Okamoto, 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 Link_out
  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 Link_out