Showing metabocard for (13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid (BMDB0001320)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:06 UTC
Update Date2020-04-22 15:07:37 UTC
BMDB IDBMDB0001320
Secondary Accession Numbers
  • BMDB01320
Metabolite Identification
Common Name(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid
Description(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid, also known as 15-keto-pge or 15-ketoprostaglandin e, 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 (13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoateChEBI
(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoateGenerator
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(13E)-11Α-hydroxy-9,15-dioxoprost-13-enoateGenerator
(13E)-11Α-hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-en-1-Oic acidHMDB
(13E)-11a-Hydroxy-9,15-dioxoprost-13-en-1-OateHMDB
(13E)-11a-Hydroxy-9,15-dioxoprost-13-en-1-Oic acidHMDB
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-en-1-OateHMDB
(13E)-11Α-hydroxy-9,15-dioxoprost-13-en-1-OateHMDB
(13E)-11Α-hydroxy-9,15-dioxoprost-13-en-1-Oic acidHMDB
(11a,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-OateHMDB
(11a,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oic acidHMDB
(11alpha,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-OateHMDB
(11alpha,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oic acidHMDB
(13E)-11-alpha-Hydroxy-9,15-dioxoprost-13-enoateHMDB
(13E)-11-alpha-Hydroxy-9,15-dioxoprost-13-enoic acidHMDB
1-Hydroxy-9,15-dioxo-(11a,13E)-prost-13-en-1-OateHMDB
1-Hydroxy-9,15-dioxo-(11a,13E)-prost-13-en-1-Oic acidHMDB
15-Keto pge1HMDB
15-Keto-pgeHMDB
15-Keto-pge1HMDB
15-Keto-pge1-alphaHMDB
15-Keto-prostaglandin e1HMDB
15-Ketoprostaglandin eHMDB
15-Ketoprostaglandin e1HMDB
15-oxo-PGE1HMDB
15-Oxoprostaglandin e1HMDB
3-Hydroxy-5-oxo-2-(3-oxo-1-octenyl)-cyclopentaneheptanoateHMDB
3-Hydroxy-5-oxo-2-(3-oxo-1-octenyl)-cyclopentaneheptanoic acidHMDB
9,15-Dioxo-11R-hydroxy-13E-prostaenoateHMDB
9,15-Dioxo-11R-hydroxy-13E-prostaenoic acidHMDB
15-Ketoprostaglandin e, (11alpha,13E)-(+-)-isomerHMDB
15-Ketoprostaglandin e, (5Z,11alpha)-isomer, 2H-labeledHMDB
(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]heptanoic acid
Traditional Name15-keto-PGE1
CAS Registry Number22973-19-9
SMILES
CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(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/h12-13,16-17,19,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t16-,17-,19-/m1/s1
InChI KeyVXPBDCBTMSKCKZ-XQHNHVHJSA-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
  • Acryloyl-group
  • Cyclic alcohol
  • Alpha,beta-unsaturated ketone
  • Enone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen 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
logP3.37ALOGPS
logP4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity97.42 m³·mol⁻¹ChemAxon
Polarizability40.82 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, Positivesplash10-0a73-4493000000-7afaed84554e2aae2cf3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9232500000-829cb1416e261a7ba8c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0029000000-f2f450b9685be184ed1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3195000000-c23605f4f8d2643eb82dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9210000000-5074a22ffbd739e04ae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-752588d05f0e2fdd0067View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kar-3179000000-3b28a2981bea2ee1e003View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9541000000-f6b425d6e7c9b00d2904View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0019000000-e0f31367a5bbff89dc21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m0-0096000000-a9f7a1c74265de9388d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-9440000000-5c468dddf050f13380e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-625cac5f8b03cab5ca64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-6459000000-a9a8193066f0828df6afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9300000000-ac7ad302bae51f1c2269View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001320
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022553
KNApSAcK IDNot Available
Chemspider ID4444295
KEGG Compound IDC04654
BioCyc IDNot Available
BiGG ID44269
Wikipedia LinkNot Available
METLIN ID6157
PubChem Compound5280710
PDB IDNot Available
ChEBI ID15548
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available