Record Information
Version1.0
Creation date2011-09-21 00:32:32 UTC
Update date2017-10-04 22:50:50 UTC
Primary IDFDB023622
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). 8-iso-prostaglandin F2A is a biomarker for the consumption of offal meat. 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. [HMDB]
CAS Number27415-26-5
Structure
Thumb
Synonyms
SynonymSource
(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
8-Epi-pgf2aGenerator
8-epi-PGF2alphahmdb
8-Epi-pgf2αGenerator
8-Epi-prostaglandin F2aGenerator
8-Epi-prostaglandin F2alphahmdb
8-Epi-prostaglandin F2αGenerator
8-Epiprostaglandin F2aGenerator
8-Epiprostaglandin F2alphahmdb
8-Epiprostaglandin F2αGenerator
8-iso-PGF2ahmdb
8-Iso-pgf2a-iiiGenerator
8-iso-PGF2alphahmdb
8-Iso-pgf2alpha-iiiChEBI
8-Iso-pgf2αGenerator
8-Iso-pgf2α-iiiGenerator
8-Isoprostaglandin F2alphahmdb
8-Isoprostaglandin F2αGenerator
9,11,15-trihydroxy Prosta-5,13-dien-1-oatehmdb
9,11,15-trihydroxy Prosta-5,13-dien-1-oic acidhmdb
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
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m³·mol⁻¹ChemAxon
Polarizability41.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H34O5
IUPAC name7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
InChI IdentifierInChI=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)/t15-,16-,17+,18-,19+/m0/s1
InChI KeyPXGPLTODNUVGFL-QXCZDIPSSA-N
Isomeric SMILES[H]C(=C[C@@]1([H])[C@]([H])(O)C[C@]([H])(O)[C@@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
Classification
Description 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
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4445435
ChEMBL IDCHEMBL1592632
KEGG Compound IDC13809
Pubchem Compound ID5282263
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05083
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference