Showing metabocard for Prostaglandin E2 (BMDB0001220)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:42:44 UTC
Update Date2020-05-21 16:28:39 UTC
MCDB ID BMDB0001220
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
MOLSDFPDBSMILESInChI
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0059-4920000000-6108934d406ea40627612014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-4920000000-6108934d406ea40627612017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a73-5395000000-02aad995307bb6a67f942017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ufu-9100850000-7394ff4333bcac154ae52017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, Negativesplash10-00yi-0398000000-41c3a62b076046d873812012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, Negativesplash10-00di-0495000000-df406a9e4cc995523a7e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, Negativesplash10-00dr-0592000000-928e66269ab2854faa422012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, Negativesplash10-00dr-0590000000-b364a55fc0598d9265b52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, Negativesplash10-00dr-0890000000-b3a25d975f2a38d7e49f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, Negativesplash10-0079-0960000000-c67461d3bd965cbf289c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, Negativesplash10-000i-0920000000-830ad149a4fe8f36e2112012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, Negativesplash10-07br-0910000000-35e5bd204c947e2c4bcc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, Negativesplash10-05fs-0900000000-573b0c5a4593210b387a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00yi-0398000000-612bce8f105beae0c5f22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0495000000-78584a9b664c5155b4732017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0592000000-b37d658cf7b0d590aad42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0590000000-985f93ab468aa6a8a1b82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0890000000-5757ca5e8720a47086dc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0079-0960000000-c67461d3bd965cbf289c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0920000000-830ad149a4fe8f36e2112017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-07br-0910000000-35e5bd204c947e2c4bcc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-05fs-0900000000-573b0c5a4593210b387a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0294000000-9d89acbe9e631d718a4b2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-31e36b1c042e1f53c0af2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2197000000-e7ed45d4821537db05982017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lmv-9110000000-b4cb6476f830b7047f382017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-a8c5f8d16d784c75721a2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kar-2159000000-92926ade35f53b386f302017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9421000000-f62f4a6586c94d0d622e2017-07-26View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0001220
DrugBank IDDB00917
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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 ]