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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 15:30:55 UTC
Update Date2021-09-23 15:30:55 UTC
HMDB IDHMDB0302207
Secondary Accession NumbersNone
Metabolite Identification
Common NameProstaglandin E-2
DescriptionProstaglandin e-2 is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds 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. Prostaglandin e-2 is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Prostaglandin e-2 can be found in soft-necked garlic, which makes prostaglandin e-2 a potential biomarker for the consumption of this food product.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-{3-hydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl}hept-5-enoic acid
Traditional Name(5Z)-7-{3-hydroxy-2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl}hept-5-enoic acid
CAS Registry NumberNot Available
SMILES
CCCCCC(O)\C=C\C1C(O)CC(=O)C1C\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+
InChI KeyXEYBRNLFEZDVAW-ZQDYKODVSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability40.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+192.60732859911
AllCCS[M+H-H2O]+189.93432859911
AllCCS[M+Na]+195.78232859911
AllCCS[M+NH4]+195.07532859911
AllCCS[M-H]-191.17732859911
AllCCS[M+Na-2H]-192.52332859911
AllCCS[M+HCOO]-194.15732859911
DeepCCS[M+H]+198.62430932474
DeepCCS[M-H]-196.26630932474
DeepCCS[M-2H]-229.15230932474
DeepCCS[M+Na]+204.71730932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin E-2,4TMS,isomer #1CCCCCC(/C=C/C1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C2816.5Semi standard non polar33892256
Prostaglandin E-2,4TMS,isomer #1CCCCCC(/C=C/C1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C2855.2Standard non polar33892256
Prostaglandin E-2,4TMS,isomer #1CCCCCC(/C=C/C1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C2924.6Standard polar33892256
Prostaglandin E-2,4TMS,isomer #2CCCCCC(/C=C/C1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2812.7Semi standard non polar33892256
Prostaglandin E-2,4TMS,isomer #2CCCCCC(/C=C/C1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2836.1Standard non polar33892256
Prostaglandin E-2,4TMS,isomer #2CCCCCC(/C=C/C1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3006.8Standard polar33892256
Prostaglandin E-2,4TBDMS,isomer #1CCCCCC(/C=C/C1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3762.6Semi standard non polar33892256
Prostaglandin E-2,4TBDMS,isomer #1CCCCCC(/C=C/C1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3545.8Standard non polar33892256
Prostaglandin E-2,4TBDMS,isomer #1CCCCCC(/C=C/C1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3183.8Standard polar33892256
Prostaglandin E-2,4TBDMS,isomer #2CCCCCC(/C=C/C1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3734.6Semi standard non polar33892256
Prostaglandin E-2,4TBDMS,isomer #2CCCCCC(/C=C/C1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3418.3Standard non polar33892256
Prostaglandin E-2,4TBDMS,isomer #2CCCCCC(/C=C/C1C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3236.7Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 10V, Positive-QTOFsplash10-00kr-0019000000-31e36b1c042e1f53c0af2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 20V, Positive-QTOFsplash10-014r-2197000000-e7ed45d4821537db05982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 40V, Positive-QTOFsplash10-0lmv-9110000000-b4cb6476f830b7047f382016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 10V, Negative-QTOFsplash10-0udi-0019000000-a8c5f8d16d784c75721a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 20V, Negative-QTOFsplash10-0kar-2159000000-92926ade35f53b386f302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 40V, Negative-QTOFsplash10-0a4i-9421000000-f62f4a6586c94d0d622e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 10V, Positive-QTOFsplash10-014i-0009000000-ad725525d25ad576536d2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 20V, Positive-QTOFsplash10-014i-4289000000-1d06c57536d9cf1761f92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 40V, Positive-QTOFsplash10-014u-9800000000-a2144167462af022d6f92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 10V, Negative-QTOFsplash10-00lr-0049000000-1d1e45c7e0b65ddd683e2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 20V, Negative-QTOFsplash10-001i-0097000000-dcf0f9c62138180378632021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin E-2 40V, Negative-QTOFsplash10-001i-8590000000-6ae1006cdd7f503886982021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003673
KNApSAcK IDNot Available
Chemspider ID17347141
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16219826
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available