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Record Information
Version3.6
Creation Date2006-10-25 11:03:23 UTC
Update Date2016-02-11 01:07:04 UTC
HMDB IDHMDB05083
Secondary Accession NumbersNone
Metabolite Identification
Common Name8-Isoprostaglandin F2a
Description8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism involving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845 , 17012140 ). 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
Synonyms
ValueSource
8-Epi-PGF2alphaChEBI
8-Epiprostaglandin F2alphaChEBI
8-iso-PGF2alphaChEBI
8-iso-PGF2alpha-IIIChEBI
8-Isoprostaglandin F2alphaChEBI
8-IsoprostaneChEBI
9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acidChEBI
8-Epi-PGF2aGenerator
8-Epi-PGF2αGenerator
8-Epi-prostaglandin F2aGenerator
8-Epi-prostaglandin F2αGenerator
8-Epiprostaglandin F2aGenerator
8-Epiprostaglandin F2αGenerator
8-iso-PGF2aGenerator
8-iso-PGF2αGenerator
8-iso-PGF2a-IIIGenerator
8-iso-PGF2α-iiiGenerator
8-Isoprostaglandin F2aGenerator
8-Isoprostaglandin F2αGenerator
9,11,15-Trihydroxy-prosta-5,13-dien-1-OateGenerator
(5Z,13E,15S)-9alpha,11alpha,15-Trihydroxy-8beta-prosta-5,13-dien-1-OateHMDB
(5Z,13E,15S)-9alpha,11alpha,15-Trihydroxy-8beta-prosta-5,13-dien-1-Oic acidHMDB
8-Epi PGF-2alphaHMDB
9,11,15-Trihydroxy prosta-5,13-dien-1-OateHMDB
9,11,15-Trihydroxy prosta-5,13-dien-1-Oic acidHMDB
9S,11R,15S-Trihydroxy-5Z,13E-prostadienoateHMDB
9S,11R,15S-Trihydroxy-5Z,13E-prostadienoic acidHMDB
9S,11R,15S-Trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]HMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name8-isoprostane
CAS Registry Number27415-26-5
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=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 KeyInChIKey=PXGPLTODNUVGFL-NAPLMKITSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Carbocyclic fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.183Not Available
Predicted Properties
PropertyValueSource
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
Polarizability41.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000957 +/- 0.00102 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000079 +/- 0.0000096 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00057 +/- 0.000057 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00038 +/- 0.000048 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000151 +/- 1.8E-5 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00027 +/- 0.00011 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00022 +/- 0.000019 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00018 +/- 0.000059 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.00019 +/- 0.0001 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023622
KNApSAcK IDNot Available
Chemspider ID4445435
KEGG Compound IDC13809
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05083
Metagene LinkHMDB05083
METLIN IDNot Available
PubChem Compound5282263
PDB IDNot Available
ChEBI ID34505
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roberts LJ 2nd, Morrow JD: Isoprostanes. Novel markers of endogenous lipid peroxidation and potential mediators of oxidant injury. Ann N Y Acad Sci. 1994 Nov 15;744:237-42. [7825845 ]
  2. Berg K, Haaverstad R, Astudillo R, Bjorngaard M, Skarra S, Wiseth R, Basu S, Jynge P: Oxidative stress during coronary artery bypass operations: importance of surgical trauma and drug treatment. Scand Cardiovasc J. 2006 Oct;40(5):291-7. [17012140 ]