| Common Name |
8-iso-PGF3a
| Description |
8-iso-PGF3alpha is an isoprostane with an antiaggregatory action in human blood. Isoprostanes (IsoPs) are formed in vivo from the free radical-catalyzed peroxidation of arachidonate independent of cyclooxygenase (COX). Although the structures of these compounds are very similar to COX-derived prostaglandins (PGs), an important distinction between IsoPs and PGs is that IsoP bicycloendoperoxide intermediates contain side chains that are predominantly (>90%) oriented cis in relation to the prostane ring because the generation of these intermediates is favored kinetically. In contrast to other types of prostanoids, E2/D2-IsoPs are beta-hydroxyketone-containing compounds that can undergo reversible keto-enol tautomerization under both acidic and basic conditions, allowing rearrangement of the side chains that are initially cis to the more stable trans-configuration. (PMID: 12746435 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(5Z,8b,9a,11a,13E,15S,17Z)-9,11,15-Trihydroxy-prosta-5,13,17-trien-1-OateHMDB
(5Z,8b,9a,11a,13E,15S,17Z)-9,11,15-Trihydroxy-prosta-5,13,17-trien-1-Oic acidHMDB
7-[3a,5a-Dihydroxy-2-(3-hydroxy-1,5-octadienyl)cyclopentyl]-5-heptenoateHMDB
7-[3a,5a-Dihydroxy-2-(3-hydroxy-1,5-octadienyl)cyclopentyl]-5-heptenoic acidHMDB
8-iso-PGF3alphaHMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoateHMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoic acidHMDB
9S,11R,15S-Trihydroxy-5Z,13E,17Z-prostatrienoic acid-cyclo[8S,12R]HMDB
| Chemical Formlia |
C20H32O5
| Average Molecliar Weight |
352.4651
| Monoisotopic Molecliar Weight |
352.224974134
| IUPAC Name |
(5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]cyclopentyl]hept-5-enoic acid
| Traditional Name |
8-iso-PGF3α
| CAS Registry Number |
7045-31-0
| SMILES |
CCC=C/C[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/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/h3-4,6-7,12-13,15-19,21-23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16-,17+,18-,19+/m0/s1
| InChI Key |
SAKGBZWJAIABSY-PJCXKLBTSA-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 Solubility0.11 mg/mLALOGPS
logP3.7ALOGPS
logP2.25ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity101.59 m3·mol-1ChemAxon
Polarizability40.35 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 |
FDB022859
| KNApSAcK ID |
Not Available
| Chemspider ID |
4446338
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB02132
| Metagene Link |
HMDB02132
| METLIN ID |
Not Available
| PubChem Compound |
5283217
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Sulfacarbamide
References |
| Synthesis Reference |
Beal, Philip F., III; Fonken, Gunther S.; Pike, John E. Microbiological conversions of unsaturated fatty acids. (1965), 34 pp. BE 659984 19650819 CAN 64:87998 AN 1966:87998 |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Gao L, Zackert WE, Hasford JJ, Danekis ME, Milne GL, Remmert C, Reese J, Yin H, Tai HH, Dey SK, Porter NA, Morrow JD: Formation of prostaglandins E2 and D2 via the isoprostane pathway: a mechanism for the generation of bioactive prostaglandins independent of cyclooxygenase. J Biol Chem. 2003 Aug 1;278(31):28479-89. Epub 2003 May 13. [PubMed:12746435 ]
|
PMID: 17043671