| Common Name |
8-isoprostaglandin PGF2b
| Description |
8-isoprostaglandin PGF2beta is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumliate to substantial levels in many clinical conditions characterized in part by accumliation 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 moleclies are not inert, but in fact evoke powerfli 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 )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 moleclies 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
8-iso-PGF2bHMDB
8-iso-PGF2betaHMDB
8-Isoprostaglandin PGF2betaHMDB
9R,11R,15S-Trihydroxy-5Z,13E-prostadienoateHMDB
9R,11R,15S-Trihydroxy-5Z,13E-prostadienoic acidHMDB
9R,11R,15S-Trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]HMDB
8-iso-PGF(2beta)MeSH
| Chemical Formlia |
C20H34O5
| Average Molecliar Weight |
354.481
| Monoisotopic Molecliar Weight |
354.240624198
| IUPAC Name |
(5Z)-7-[(1S,2R,3R,5R)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
| Traditional Name |
8-iso-PGF2β
| CAS Registry Number |
177020-26-7
| SMILES |
CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@@H](O)[C@H]1CC=C/CCCC(O)=O
| InChI Identifier |
InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18+,19+/m0/s1
| InChI Key |
PXGPLTODNUVGFL-HMALSPAFSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.12 mg/mLALOGPS
logP3.11ALOGPS
logP2.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m3·mol-1ChemAxon
Polarizability41.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
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
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022851
| KNApSAcK ID |
Not Available
| Chemspider ID |
4446337
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02115
| Metagene Link |
HMDB02115
| METLIN ID |
Not Available
| PubChem Compound |
5283216
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: 3-Cyano-7-ethoxycoumarin
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Tazzeo T, Miller J, Janssen LJ: Vasoconstrictor responses, and underlying mechanisms, to isoprostanes in human and porcine bronchial arterial smooth muscle. Br J Pharmacol. 2003 Oct;140(4):759-63. Epub 2003 Sep 22. [PubMed:14504139 ]
|
PMID: 18486111