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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:12 UTC
HMDB IDHMDB0001320
Secondary Accession Numbers
  • HMDB0011598
  • HMDB01320
  • HMDB11598
Metabolite Identification
Common Name(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid
Description(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid is a substrate for Carbonyl reductase 1.Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Structure
Data?1582752192
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a73-4493000000-7afaed84554e2aae2cf3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9232500000-829cb1416e261a7ba8c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0029000000-f2f450b9685be184ed1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3195000000-c23605f4f8d2643eb82dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9210000000-5074a22ffbd739e04ae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-752588d05f0e2fdd0067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kar-3179000000-3b28a2981bea2ee1e003Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9541000000-f6b425d6e7c9b00d2904Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73