Showing metabocard for 8-iso-15-keto-PGE2 (BMDB0002341)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:54:18 UTC
Update Date2020-04-22 15:10:43 UTC
BMDB IDBMDB0002341
Secondary Accession Numbers
  • BMDB02341
Metabolite Identification
Common Name8-iso-15-keto-PGE2
Description8-iso-15-keto-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. Based on a literature review very few articles have been published on 8-iso-15-keto-PGE2.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8b,11a,13E)-11-Hydroxy-9,15-dioxo-prosta-5,13-dien-1-OateHMDB
(5Z,8b,11a,13E)-11-Hydroxy-9,15-dioxo-prosta-5,13-dien-1-Oic acidHMDB
8-Iso-15-keto-prostaglandine e2HMDB
(5Z)-7-[(1S,2R)-3-Hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoateHMDB
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1S,2R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name8-iso-15-keto-PGE2
CAS Registry Number914804-63-0
SMILES
CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O5/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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,19?/m0/s1
InChI KeyYRTJDWROBKPZNV-LSAJIUQUSA-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
  • Unsaturated fatty acid
  • Fatty acid
  • Alpha,beta-unsaturated ketone
  • Cyclic alcohol
  • Acryloyl-group
  • Enone
  • Secondary alcohol
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP3.27ALOGPS
logP3.64ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity98.54 m³·mol⁻¹ChemAxon
Polarizability39.99 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, Positivesplash10-052u-4493000000-0d0c2247610da9ad51deView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-002b-7318900000-e3deca635536990d3ff8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-3ef3528ac5a012ba1cf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-3079000000-e1ebbca36295283f32e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9452000000-aa26e5f3571b762113f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0019000000-319ec8417f062af25ae2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008i-0094000000-ecf8159ba7722550f80aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-9270000000-4f5b9ab71a4cd04afdc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0029000000-9303b63bd2ebcbb5c384View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067i-2195000000-4191e15aa7f06f807e38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9210000000-7c06db5bb5cf1359caabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0019000000-e747c20277d6c7786fa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-6369000000-c74c0a7bb044927841f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9200000000-e6002eb037e36f06c242View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002341
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022970
KNApSAcK IDNot Available
Chemspider ID35013045
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477750
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available