13,14-Dihydro-15-keto-PGE2 (CHEM021880)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:40 UTC
Update Date2026-04-06 10:52:35 UTC
Accession NumberCHEM021880
Identification
Common Name13,14-Dihydro-15-keto-PGE2
ClassSmall Molecule
DescriptionThe 13,14-dihydro derivative of 15-oxo-prostaglandin E2.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprostanoateChEBI
13,14-Dihydro-15-ketoprostaglandin e2ChEBI
15-Keto-13,14-dihydro-pge2ChEBI
15-Keto-13,14-dihydroprostaglandin e2ChEBI
DHK-PGE2ChEBI
KH(2)PGE(2)ChEBI
PGEMChEBI
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprostanoateGenerator
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprostanoic acidGenerator
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprostanoic acidGenerator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprostanoateGenerator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprostanoic acidGenerator
11-alpha-Hydroxy-9,15-dioxoprost-5-enoateHMDB
11-alpha-Hydroxy-9,15-dioxoprost-5-enoic acidHMDB
15-Keto-13,14-dihydroprostaglandin e2, (11alpha)-isomerHMDB
PGEM (13,14-dihydro-15-keto-pge2)HMDB
13,14-Dihydro-15-keto-pge2ChEBI
Chemical FormulaC20H32O5
Average Molecular Mass352.465 g/mol
Monoisotopic Mass352.225 g/mol
CAS Registry Number363-23-5
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
Traditional NamePGEM
SMILESCCCCCC(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
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/h4,7,16-17,19,23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,19-/m1/s1
InChI KeyCUJMXIQZWPZMNQ-XYYGWQPLSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.072 g/LALOGPS
logP3.55ALOGPS
logP3.64ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity97.44 m³·mol⁻¹ChemAxon
Polarizability40.33 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9l-6393000000-ae59241eb736ede4c95bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000t-9215600000-3536eaef2e9bc35b6f8aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fri-0019000000-a742f360f0f74c303ab1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-5395000000-4d56102adb13bd08c580Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9110000000-e75b0b5e5c30f91108c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-096b4b11fc0ed93839f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-1159-3269000000-2e041b3fc1fa4fcf221cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9521000000-3b40b00f96d516c15935Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0009000000-32de0277c190ac2633cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00si-1397000000-53d144e3e93f4a8c65cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-9240000000-4422b83ff4edef0f7476Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-b4b58012e7cfc4cfc9acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-7349000000-d7bf1a8717d95099e438Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9300000000-3ff24cdf3119504a1335Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002776
FooDB IDFDB023063
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2311
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444296
ChEBI ID15550
PubChem Compound ID5280711
Kegg Compound IDC04671
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gordon-Wright AP, Elder MG: Effect of prostaglandin E2 and its metabolites on lower segment myometrium in vitro. Eur J Obstet Gynecol Reprod Biol. 1980 Jun;10(5):297-302.
2. Hume R, Bell J, Cossar D, Giles M, Hallas A, Kelly R: Differential release of prostaglandins by organ cultures of human fetal trachea and lung. In Vitro Cell Dev Biol Anim. 1996 Jan;32(1):24-9.
3. Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7.