Showing metabocard for 8-isoprostaglandin E2 (BMDB0005844)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:19:07 UTC
Update Date2020-04-22 15:16:30 UTC
BMDB IDBMDB0005844
Secondary Accession Numbers
  • BMDB05844
Metabolite Identification
Common Name8-isoprostaglandin E2
Description8-isoprostaglandin E2, also known as 8-epi-pge2, 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. Thus, 8-isoprostaglandin E2 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 8-isoprostaglandin E2.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-[3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acidChEBI
8-Epi-pge2ChEBI
8-Iso-pge2ChEBI
7-[3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoateGenerator
(5Z,8b,11a,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-OateHMDB
(5Z,8b,11a,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-Oic acidHMDB
8-Isoprostaglandin e2ChEBI
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1S,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
Traditional Name8-Iso-PGE2
CAS Registry Number27415-25-4
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1C\C=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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,19+/m0/s1
InChI KeyXEYBRNLFEZDVAW-CLQOMRTCSA-N
Chemical Taxonomy
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
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.31ALOGPS
logP3.23ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.44 m³·mol⁻¹ChemAxon
Polarizability41.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a73-5395000000-02aad995307bb6a67f94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ufu-9302550000-70dfa502c5c46d488f7aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-f68c6b496bc66132ac05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3197000000-5c1986771d855fb6ed90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9210000000-12fff721757996d80d14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0009000000-8f0c944be1857e336476View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-2059000000-3515e7355791e5a9219fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9430000000-8cbabd2bf835ca82e917View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0049000000-1d1e45c7e0b65ddd683eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0097000000-dcf0f9c6213818037863View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-8590000000-6ae1006cdd7f50388698View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-3d13808f266c10b60336View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4289000000-1d06c57536d9cf1761f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9800000000-a2144167462af022d6f9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005844
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023780
KNApSAcK IDNot Available
Chemspider ID4446334
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283213
PDB IDNot Available
ChEBI ID131888
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available