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Showing metabocard for 8-iso-15-keto-PGE2 (HMDB02341)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:48 -0600
Update Date 2013-03-25 16:21:17 -0600
HMDB ID HMDB02341
Secondary Accession Numbers None
Metabolite Identification
Common Name 8-iso-15-keto-PGE2
Description 8-iso-15-keto-PGE2 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states (PMID: 14504139 Link_out). 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 Link_out). 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
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Display: 2D Structure | 3D Structure
Synonyms
  1. (5Z,8b,11a,13E)-11-hydroxy-9,15-dioxo-Prosta-5,13-dien-1-oate
  2. (5Z,8b,11a,13E)-11-hydroxy-9,15-dioxo-Prosta-5,13-dien-1-oic acid
  3. 8-Iso-15-keto-Prostaglandine E2
Chemical Formula C20H30O5
Average Molecular Weight 350.4492
Monoisotopic Molecular Weight 350.20932407
IUPAC Name (5Z)-7-[(1S,2R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional IUPAC Name (5Z)-7-[(1S,2R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
CAS Registry Number 914804-63-0
SMILES CCCCCC(=O)\C=C\[C@H]1C(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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,19?/m0/s1
InChI Key YRTJDWROBKPZNV-LSAJIUQUSA-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
  • Acryloyl Group
  • Carboxylic Acid
  • Cyclic Alcohol
  • Enone
  • Ketone
  • Secondary Alcohol
Direct Parent Prostaglandins and related compounds
Ontology
Status Expected and Not 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 0.058 g/L ALOGPS
LogP 3.27 ALOGPS
LogP 3.64 ChemAxon
LogS -3.78 ALOGPS
pKa (strongest acidic) 4.3 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 91.67 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 98.54 ChemAxon
Polarizability 39.99 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022970
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02341 Link_out
Metagene Link HMDB02341 Link_out
METLIN ID Not Available
PubChem Compound 53477750 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available