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Showing Compound 8-iso-PGF3a (FDB022859)

Record Information
Version1.0
Creation date2011-09-21 00:20:40 UTC
Update date2015-07-21 06:57:24 UTC
Primary IDFDB022859
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-iso-PGF3a
Description8-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) [HMDB]
CAS Number7045-31-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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-PGF3ahmdb
8-Iso-PGF3alphahmdb
9S,11R,15S-trihydroxy-5Z,13E,17Z-prostatrienoic acid-cyclo[8S,12R]hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity101.59 m³·mol⁻¹ChemAxon
Polarizability40.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O5
IUPAC name7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyocta-1,5-dien-1-yl]cyclopentyl]hept-5-enoic acid
InChI IdentifierInChI=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)/t15-,16-,17+,18-,19+/m0/s1
InChI KeySAKGBZWJAIABSY-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)CC=CCC
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
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
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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 ID4446338
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5283217
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02132
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