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Record Information
Version1.0
Creation Date2016-09-30 22:42:44 UTC
Update Date2020-05-21 16:28:39 UTC
BMDB IDBMDB0001220
Secondary Accession Numbers
  • BMDB01220
Metabolite Identification
Common NameProstaglandin E2
DescriptionProstaglandin e2, also known as dinoprostone or PGE2, 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. Thus, prostaglandin E2 is considered to be an eicosanoid lipid molecule. Prostaglandin e2 is a drug which is used for the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage. Prostaglandin e2 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Prostaglandin e2 exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
(15S)-Prostaglandin e2ChEBI
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoateChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoateChEBI
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acidChEBI
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acidChEBI
DinoprostonChEBI
DinoprostonaChEBI
DinoprostoneChEBI
DinoprostonumChEBI
PGE2ChEBI
PrepidilChEBI
PropessChEBI
Prostin e2ChEBI
CervidilKegg
(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoateGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoateGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoateGenerator
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoateGenerator
(-)-Prostaglandin e2HMDB
(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoateHMDB
(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoic acidHMDB
5-trans-PGE2HMDB
GlandinHMDB
L-Prostaglandin e2HMDB
Minprositin e2HMDB
Minprostin e2HMDB
Prostaglandin eHMDB
Prostaglandin e2alphaHMDB
Prostarmon eHMDB
ProstinHMDB
e2, ProstaglandinHMDB
Prepidil gelHMDB
alpha, Prostaglandin e2HMDB
e2 alpha, ProstaglandinHMDB
e2alpha, ProstaglandinHMDB
alpha, PGE2HMDB
ProstenonHMDB
Gel, prepidilHMDB
PGE2 alphaHMDB
PGE2alphaHMDB
Prostaglandin e2 alphaHMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
Traditional Namedinoprostone
CAS Registry Number363-24-6
SMILES
CCCCC[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/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChI KeyXEYBRNLFEZDVAW-ARSRFYASSA-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
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point67 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.82HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP3.31ALOGPS
logP3.23ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity99.44 m³·mol⁻¹ChemAxon
Polarizability41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0059-4920000000-6108934d406ea4062761View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-4920000000-6108934d406ea4062761View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a73-5395000000-02aad995307bb6a67f94View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ufu-9100850000-7394ff4333bcac154ae5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, Negativesplash10-00yi-0398000000-41c3a62b076046d87381View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, Negativesplash10-00di-0495000000-df406a9e4cc995523a7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, Negativesplash10-00dr-0592000000-928e66269ab2854faa42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, Negativesplash10-00dr-0590000000-b364a55fc0598d9265b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, Negativesplash10-00dr-0890000000-b3a25d975f2a38d7e49fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, Negativesplash10-0079-0960000000-c67461d3bd965cbf289cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, Negativesplash10-000i-0920000000-830ad149a4fe8f36e211View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, Negativesplash10-07br-0910000000-35e5bd204c947e2c4bccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, Negativesplash10-05fs-0900000000-573b0c5a4593210b387aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00yi-0398000000-612bce8f105beae0c5f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0495000000-78584a9b664c5155b473View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0592000000-b37d658cf7b0d590aad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0590000000-985f93ab468aa6a8a1b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0890000000-5757ca5e8720a47086dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0079-0960000000-c67461d3bd965cbf289cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0920000000-830ad149a4fe8f36e211View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-07br-0910000000-35e5bd204c947e2c4bccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-05fs-0900000000-573b0c5a4593210b387aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0294000000-9d89acbe9e631d718a4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-31e36b1c042e1f53c0afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2197000000-e7ed45d4821537db0598View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lmv-9110000000-b4cb6476f830b7047f38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-a8c5f8d16d784c75721aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kar-2159000000-92926ade35f53b386f30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9421000000-f62f4a6586c94d0d622eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001220
DrugBank IDDB00917
Phenol Explorer Compound IDNot Available
FooDB IDFDB022498
KNApSAcK IDNot Available
Chemspider ID4444059
KEGG Compound IDC00584
BioCyc ID5Z13E-15S-1115-DIHYDROXY-9-OXOPROS
BiGG ID35424
Wikipedia LinkProstaglandin_E2
METLIN ID6089
PubChem Compound5280360
PDB IDNot Available
ChEBI ID15551
References
Synthesis ReferenceCorey, Elias J.; Weinshenker, Ned M.; Schaaf, Thomas K.; Huber, Willy. Stereo-controlled synthesis of dl-prostaglandins F2a and E2. Journal of the American Chemical Society (1969), 91(20), 5675-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
HPGD
Uniprot ID:
Q309F3
Molecular weight:
29025.0
General function:
Lipid transport and metabolism
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 (By similarity).
Gene Name:
CBR1
Uniprot ID:
Q3SZD7
Molecular weight:
30533.0
Reactions
Prostaglandin E2 + NADPH → Prostaglandin F2a + NADPdetails
General function:
Involved in prostaglandin E receptor activity
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role in regulating renal hemodynamics, intestinal epithelial transport, adrenal aldosterone secretion, and uterine function (By similarity).
Gene Name:
PTGER4
Uniprot ID:
Q8MJ08
Molecular weight:
53298.0
General function:
Involved in prostaglandin E receptor activity
Specific function:
Not Available
Gene Name:
PTGER4
Uniprot ID:
Q1JPJ5
Molecular weight:
25029.0
General function:
Not Available
Specific function:
Receptor for prostaglandin E2 (PGE2) (PubMed:8396726). The various isoforms have identical ligand binding properties but interact with different second messenger systems: isoform EP3A couples to G(i)/G(o) proteins; isoform EP3B and isoform EP3C couple to G(s), and isoform EP3D couples to G(i), G(s) and G(p) (PubMed:8396726). Required for normal development of fever in response to pyrinogens, including IL1B, prostaglandin E2 and bacterial lipopolysaccharide (LPS). Required for normal potentiation of platelet aggregation by prostaglandin E2, and thus plays a role in the regulation of blood coagulation. Required for increased HCO3(-) secretion in the duodenum in response to mucosal acidification, and thereby contributes to the protection of the mucosa against acid-induced ulceration. Not required for normal kidney function, normal urine volume and osmolality (By similarity).
Gene Name:
PTGER3
Uniprot ID:
P34979
Molecular weight:
46362.0
General function:
Involved in prostaglandin E receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q8MJ09
Molecular weight:
39726.0
General function:
Involved in prostaglandin E receptor activity
Specific function:
Not Available
Gene Name:
ep1
Uniprot ID:
Q95M52
Molecular weight:
3120.0
General function:
Involved in prostaglandin E receptor activity
Specific function:
Not Available
Gene Name:
ep4
Uniprot ID:
Q95M50
Molecular weight:
18505.0
General function:
Involved in prostaglandin E receptor activity
Specific function:
Not Available
Gene Name:
ep2
Uniprot ID:
Q95M51
Molecular weight:
15313.0
General function:
Not Available
Specific function:
Catalyzes the oxidoreduction of prostaglandin endoperoxide H2 (PGH2) to prostaglandin E2 (PGE2).
Gene Name:
PTGES
Uniprot ID:
Q95L14
Molecular weight:
17298.0
Reactions
Prostaglandin H2 → Prostaglandin E2details