Showing metabocard for Prostaglandin E3 (BMDB0002664)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:11 UTC
Update Date2020-04-22 15:11:15 UTC
BMDB IDBMDB0002664
Secondary Accession Numbers
  • BMDB02664
Metabolite Identification
Common NameProstaglandin E3
DescriptionProstaglandin E3, also known as PGE3 or delta(17)-pge1, 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, prostaglandin E3 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on Prostaglandin E3.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acidChEBI
9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoic acidChEBI
PGE3ChEBI
(5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acidGenerator
(5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-OateGenerator
(5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acidGenerator
9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoateGenerator
(-)-Prostaglandin e3HMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoateHMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acidHMDB
7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acid stereoisomerHMDB
delta(17)-PGE1HMDB
delta(17)-Prostaglandin e1HMDB
Prostaglandin e3MeSH
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
Traditional Name(-)-prostaglandin E3
CAS Registry Number802-31-3
SMILES
CC\C=C/C[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/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/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChI KeyCBOMORHDRONZRN-QLOYDKTKSA-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
logP2.88ALOGPS
logP2.86ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity100.55 m³·mol⁻¹ChemAxon
Polarizability39.44 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, Positivesplash10-0059-7496000000-9210fb4674d794816bc0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-9101680000-a66ceba0ca4003a25001View 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, Positivesplash10-00lr-0019000000-3a37659687433065f9daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-4197000000-5a2017a0bfe4592e8fffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9220000000-feedd008762c81af1d13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0009000000-50f3213aa3eff0d0faf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-2149000000-29aed26fd57d9c5f3bc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9431000000-5c1e13cc53c44b8f766dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-5c376e396ab8f47ce7dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4196000000-1567e644caaefea5e0dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9700000000-9dfab3d79c88fcbb1ec7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-87bc754463331ba5961aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0096000000-6b6024dbd45dd4f026a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9480000000-a2fb3e9a5f2bfee6385bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002664
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023042
KNApSAcK IDNot Available
Chemspider ID4444439
KEGG Compound IDC06439
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProstaglandin E3
METLIN ID3494
PubChem Compound5280937
PDB IDNot Available
ChEBI ID28031
References
Synthesis ReferenceOkamoto, Sentaro; Kobayashi, Yuichi; Sato, Fumie. A highly efficient synthesis of natural PGE3 and 5,6-dihydro PGE3 via two-component coupling process. Tetrahedron Letters (1989), 30(33), 4379-82.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available