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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:44 UTC
Update Date2020-02-26 21:24:27 UTC
HMDB IDHMDB0003247
Secondary Accession Numbers
  • HMDB03247
Metabolite Identification
Common Name20-Hydroxy-PGE2
Description20-hydroxy PGE2 is a product of cytochrome P450 metabolism of PGE2. ω-Oxidation at C-20 followed by beta-oxidation and the loss of up to 4 carbons from the lower side chain is a prominent metabolic pathway for PGE2. 20-hydroxy PGE2 is the putative first intermediate in this chain of chemical transformations. -- www.caymanchem.com. Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535 )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?1582752267
Synonyms
ValueSource
(5Z,11alpha,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oic acidChEBI
20-Hydroxy prostaglandin e2ChEBI
20-Hydroxy-prostaglandin e2ChEBI
20-OH-PGE2ChEBI
9-oxo-11R,15S,20-Trihydroxy-5Z,13E-prostadienoic acidChEBI
(5Z,11a,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11a,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,11alpha,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15,20-trihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15,20-trihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
9-oxo-11R,15S,20-Trihydroxy-5Z,13E-prostadienoateGenerator
(5Z,11(alpha),13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-OateHMDB
(5Z,11(alpha),13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-Oic acidHMDB
20-Hydroxyprostaglandin e2HMDB
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
IUPAC Name(5Z)-7-[(1R,2R,3R)-2-[(1E,3S)-3,8-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid
Traditional Name20-Hydroxy-PGE2
CAS Registry Number57930-95-7
SMILES
OCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O6/c21-13-7-3-4-8-15(22)11-12-17-16(18(23)14-19(17)24)9-5-1-2-6-10-20(25)26/h1,5,11-12,15-17,19,21-22,24H,2-4,6-10,13-14H2,(H,25,26)/b5-1-,12-11+/t15-,16+,17+,19+/m0/s1
InChI KeyAZIGEYVZEVXWAD-NZGURKHLSA-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
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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 Solubility0.23 g/LALOGPS
logP2.02ALOGPS
logP1.79ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.36 m³·mol⁻¹ChemAxon
Polarizability41.56 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, Positivesplash10-0udv-2496000000-99122637177145628ab2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0006-9300368000-b5e56740df85f5d1a0a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0009000000-ebd1464d44ae0ca6b6a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0149000000-230b542bf2b718260276Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9531000000-fe0172c7250e86fb8008Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0009000000-de1b715838573884563eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0019000000-173f7be02a65564b8220Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9443000000-589d4f940035f349cf6bSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB023129
KNApSAcK IDNot Available
Chemspider ID4446161
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3814
PubChem Compound5283034
PDB IDNot Available
ChEBI ID137370
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Oliw EH, Fahlstadius P, Hamberg M: Biosynthesis of 19-hydroxy and 20-hydroxy E prostaglandins in seminal fluids. Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:39-43. [PubMed:2959084 ]
  2. Oliw EH, Johnsen O: Rapid and slow hydroxylators of seminal E prostaglandins. Biochim Biophys Acta. 1988 Nov 25;963(2):295-301. [PubMed:3196735 ]
  3. Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [PubMed:16978535 ]