Record Information
Version1.0
Creation date2011-09-21 00:28:26 UTC
Update date2015-07-21 06:57:39 UTC
Primary IDFDB023346
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6-Ketoprostaglandin E1
Description6-Ketoprostaglandin E1(6-keto PGE1) is a biologically active and stable prostacyclin (PGI2) metabolite and a substrate for Adenylate cyclase type III. 6-keto PGE1 is a potent coronary vasodilator. 6-keto PGE1 could be elevated in plasma of patients with primary thrombocythaemia. 6-keto-PGE1 has approximately four times less potent antiplatelet activity than PGI2 on a molar basis in man. The cardiovascular and plasma renin activity (PRA) changes are less prominent for 6-keto-PGE1 than PGI2. Salt loading slightly increases urinary 6-keto PGE1. 6-keto-PGE1 elicits the same biological effects as PGI2 in human platelets and in rabbit aorta and mesenteric artery, being, however, less potent. 6-keto-PGE1 dose-dependently stimulates adenylate cyclase activity in membranes of human platelets and cultured myocytes from rabbit aorta and mesenteric artery. The extent of stimulation of the enzyme by 6-keto-PGE1 is the same as elicited by PGI2, while the apparent affinity is lower than that of prostacyclin, both in platelets and in vascular smooth muscle cells. At the level of platelet membranes, 6-keto-PGE1 interacts with the binding sites labelled by PGI2. However, in platelets as well as in mesenteric artery myocytes, 6-keto-PGE1 interacts with only one class of sites as demonstrated either by binding or by adenylate cyclase studies, whereas PGI2 in the same conditions recognizes two different classes. (PMID: 3186779, 3075239, 3472253, 3912001, 3881881, 6391491) 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 signaling pathways. [HMDB]
CAS Number67786-53-2
Structure
Thumb
Synonyms
SynonymSource
6-Keto-pge1ChEBI
6-Keto-prostaglandin e1ChEBI
6-oxo-PGE1ChEBI
6-Oxoprostaglandin e1HMDB
6,9-Dioxo-11R,15S-dihydroxy-13E-prostenoateHMDB
6,9-Dioxo-11R,15S-dihydroxy-13E-prostenoic acidHMDB
6-Keto pge1HMDB
6-KPGE1HMDB
6-oxo-Prostaglandin e1HMDB
6-keto PGE1hmdb
6-Keto-PGE1hmdb
6-keto-Prostaglandin e1ChEBI
6-ketoprostaglandin E1hmdb
6-Oxo-PGE1hmdb
6-oxo-prostaglandin E1hmdb
6-Oxoprostaglandin E1hmdb
6,9-dioxo-11R,15S-dihydroxy-13E-prostenoatehmdb
6,9-dioxo-11R,15S-dihydroxy-13E-prostenoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.02ALOGPS
logP2.41ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.96 m³·mol⁻¹ChemAxon
Polarizability42.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H32O6
IUPAC name7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]-6-oxoheptanoic acid
InChI IdentifierInChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-18,21,23H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+/m0/s1
InChI KeyROUDCKODIMKLNO-CTBSXBMHSA-N
Isomeric SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CC(=O)CCCCC(O)=O
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
Classification
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
  • Fatty alcohol
  • Hydroxy fatty acid
  • Keto fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-005l-5920000000-5d82d8d407a98a19595aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0040-5920000000-b930e702a5edfe6a21b8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-005l-5920000000-5d82d8d407a98a19595aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0040-5920000000-b930e702a5edfe6a21b8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbc-9785000000-e00c3d94ffc45296f22aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xu-9010370000-39dd50540f235321f2afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0019000000-45e089848974d223c817JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-4259000000-5a1d119bcb0808abb167JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg3-9420000000-67d99bbd6776618bd2a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0009000000-f8af87f67576792f65d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-2289000000-d9d9ce800ce279bd0e23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9531000000-3a8f481b219ca74ab254JSpectraViewer
ChemSpider ID4444412
ChEMBL IDCHEMBL138482
KEGG Compound IDC05962
Pubchem Compound ID5280889
Pubchem Substance IDNot Available
ChEBI ID28269
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04241
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference