Showing metabocard for 13,14-Dihydro-15-keto-PGE2 (BMDB0002776)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:35 UTC
Update Date2020-04-22 15:11:23 UTC
BMDB IDBMDB0002776
Secondary Accession Numbers
  • BMDB02776
Metabolite Identification
Common Name13,14-Dihydro-15-keto-PGE2
Description13,14-Dihydro-15-keto-PGE2, also known as 15-keto-13,14-dihydro-pge2 or DHK-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, 13,14-dihydro-15-keto-pge2 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 13,14-Dihydro-15-keto-PGE2.
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 Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
Traditional NamePGEM
CAS Registry Number363-23-5
SMILES
CCCCCC(=O)CC[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/h4,7,16-17,19,23H,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
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
logP3.55ALOGPS
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
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, Positivesplash10-0k9l-6393000000-ae59241eb736ede4c95bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000t-9215600000-3536eaef2e9bc35b6f8aView 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, Positivesplash10-0fri-0019000000-a742f360f0f74c303ab1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-5395000000-4d56102adb13bd08c580View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9110000000-e75b0b5e5c30f91108c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-096b4b11fc0ed93839f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-1159-3269000000-2e041b3fc1fa4fcf221cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9521000000-3b40b00f96d516c15935View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0009000000-32de0277c190ac2633cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00si-1397000000-53d144e3e93f4a8c65cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-9240000000-4422b83ff4edef0f7476View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-b4b58012e7cfc4cfc9acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-7349000000-d7bf1a8717d95099e438View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9300000000-3ff24cdf3119504a1335View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002776
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023063
KNApSAcK IDNot Available
Chemspider ID4444296
KEGG Compound IDC04671
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2311
PubChem Compound5280711
PDB IDNot Available
ChEBI ID15550
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Prostaglandin reductase 1
General function:
Involved in 15-oxoprostaglandin 13-oxidase activity
Specific function:
Functions as 15-oxo-prostaglandin 13-reductase and acts on 15-oxo-PGE1, 15-oxo-PGE2 and 15-oxo-PGE2-alpha. Has no activity towards PGE1, PGE2 and PGE2-alpha. Catalyzes the conversion of leukotriene B4 into its biologically less active metabolite, 12-oxo-leukotriene B4. This is an initial and key step of metabolic inactivation of leukotriene B4 (By similarity).
Gene Name:
PTGR1
Uniprot ID:
Q3SZJ4
Molecular weight:
35706.0
Enzyme Details
2. Prostaglandin reductase 2
General function:
Involved in 15-oxoprostaglandin 13-oxidase activity
Specific function:
Functions as 15-oxo-prostaglandin 13-reductase and acts on 15-keto-PGE1, 15-keto-PGE2, 15-keto-PGE1-alpha and 15-keto-PGE2-alpha with highest activity towards 15-keto-PGE2. Overexpression represses transcriptional activity of PPARG and inhibits adipocyte differentiation (By similarity).
Gene Name:
PTGR2
Uniprot ID:
Q32L99
Molecular weight:
38400.0