Showing metabocard for 15-Keto-prostaglandin E2 (BMDB0003175)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:03:01 UTC
Update Date2020-04-22 15:11:48 UTC
BMDB IDBMDB0003175
Secondary Accession Numbers
  • BMDB03175
Metabolite Identification
Common Name15-Keto-prostaglandin E2
Description15-Keto-prostaglandin E2, also known as 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. Thus, 15-keto-prostaglandin E2 is considered to be an eicosanoid. Based on a literature review a small amount of articles have been published on 15-Keto-prostaglandin E2.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoateChEBI
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoateChEBI
15-Deoxy-15-oxo-prostaglandin e2ChEBI
15-Keto-pge2ChEBI
15-Ketoprostaglandin e2ChEBI
15-oxo-PGE2ChEBI
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoateGenerator
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoateGenerator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoateGenerator
(5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoateGenerator
(5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoateHMDB
(5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoic acidHMDB
(5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoateHMDB
(5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoic acidHMDB
15-Keto-pge2-alphaHMDB
15-oxo-PGE2-alphaHMDB
9,15-Dioxo-11-hydroxyprosta-5,13-dienoic acidHMDB
15-Ketoprostaglandin e2, (11alpha)-isomerHMDB
15-Keto-prostaglandin e2ChEBI
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name15-Keto-PGE2
CAS Registry Number26441-05-4
SMILES
CCCCCC(=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/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-/m1/s1
InChI KeyYRTJDWROBKPZNV-KMXMBPPJSA-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 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
logP3.27ALOGPS
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
Polarizability40.05 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, Positivesplash10-00b9-4101900000-afa0e89ef36aaefae13aView 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-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, 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, Positivesplash10-0159-0019000000-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 IDHMDB0003175
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023119
KNApSAcK IDNot Available
Chemspider ID4444303
KEGG Compound IDC04707
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2309
PubChem Compound5280719
PDB IDNot Available
ChEBI ID15547
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