You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-14 00:26:01 UTC
Update Date2016-02-11 01:06:47 UTC
HMDB IDHMDB04685
Secondary Accession NumbersNone
Metabolite Identification
Common Name13,14-Dihydro-15-keto PGF2a
Description13,14-dihydro-15-keto PGF2a E1 is an isoprostane. The isoprostanes embody a vast family of novel prostaglandin-like lipids that are produced by nonenzymatic peroxidation of arachidonic acid (AA) in response to free radicals and reactive oxygen species. Although free AA is required for the formation of prostaglandins by cyclooxygenases, the isoprostanes can be generated nonenzymatically from esterified AA in membrane phospholipids before being released by a phospholipase(s). Another dissimilarity is that isoprostanes feature side chains that are almost exclusively orientated cis relative to the cyclopentane ring and are therefore distinct from the prostaglandins, which always have side chains in the trans configuration. Nevertheless, isoprostanes are isomeric with prostaglandins and have been given the prefix D-, E-, and F{alpha}- to denote the prostane ring shared with PGD2, PGE2, and PGF2{alpha} respectively. An additional level of complexity is that peroxidation of AA can occur at one of any of four carbon atoms producing regioisomers, the so-called 5-, 12-, 8-, and 15-series isoprostanes, each consisting of eight racemic diastereomers. Thus, a total of 64 isomers can be generated for each of the D-, E-, and F{alpha}-ring isoprostanes. (PMID: 15528403 ). 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.
Structure
Thumb
Synonyms
ValueSource
13,14-dihydro-15-keto-Prostaglandin F2aChEBI
13,14-dihydro-15-Ketoprostaglandin F2alphaChEBI
15-keto-13,14-dihydro-PGF2alphaChEBI
15-keto-13,14-Dihydroprostaglandin F2-alphaChEBI
15-keto-13,14-Dihydroprostaglandin F2alphaChEBI
9S,11S-Dihydroxy-15-oxo-5Z-prostenoic acidChEBI
DHK-PGF2alphaChEBI
PGFMChEBI
13,14-dihydro-15-keto PGF2alphaHMDB
13,14-dihydro-15-keto-PGF2alphaHMDB
13,14-dihydro-15-Ketoprostaglandin FHMDB
13,14-dihydro-15-Oxoprostaglandin FHMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
Traditional Name13,14-dihydro-15-keto-PGF2α
CAS Registry Number27376-76-7
SMILES
CCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O5/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/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,18+,19-/m1/s1
InChI KeyInChIKey=VKTIONYPMSCHQI-XAGFEHLVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Carbocyclic fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclopentanol
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
Water Solubility0.11 mg/mLALOGPS
logP3.12ALOGPS
logP3.02ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.31ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity98.48 m3·mol-1ChemAxon
Polarizability41 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000235 +/- 2.8E-5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00016 (0.00018-0.0003) uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0026 +/- 0.001 uMAdult (>18 years old)Female
Pregnancy with RU486 administration
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Yang XL, Wu XR: The dynamic changes of several reproductive hormones during termination of early pregnancy by RU486 in combination with PG-05 in Chinese women. Adv Contracept. 1988 Dec;4(4):319-26. [3252730 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023404
KNApSAcK IDNot Available
Chemspider ID4446166
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04685
Metagene LinkHMDB04685
METLIN IDNot Available
PubChem Compound5283039
PDB IDNot Available
ChEBI ID63976
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Clarke DL, Belvisi MG, Hardaker E, Newton R, Giembycz MA: E-ring 8-isoprostanes are agonists at EP2- and EP4-prostanoid receptors on human airway smooth muscle cells and regulate the release of colony-stimulating factors by activating cAMP-dependent protein kinase. Mol Pharmacol. 2005 Feb;67(2):383-93. Epub 2004 Nov 4. [15528403 ]