Dinoprostone (CHEM016673)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:40:02 UTC
Update Date2026-04-13 20:38:02 UTC
Accession NumberCHEM016673
Identification
Common NameDinoprostone
ClassSmall Molecule
DescriptionProstaglandin E2 is a naturally occurring prostaglandin E2 (PGE2). It has important effects in labour. It also stimulates osteoblasts to release factors which stimualtes bone resorption by osteoclasts. As a prescription drug it is used as a vaginal suppository, to prepare the cervix for labour and to induce labour.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass352.465 g/mol
Monoisotopic Mass352.225 g/mol
CAS Registry Number363-24-6
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
SMILESCCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0059-4920000000-6108934d406ea4062761Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-4920000000-6108934d406ea4062761Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a73-5395000000-02aad995307bb6a67f94Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ufu-9100850000-7394ff4333bcac154ae5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, Negativesplash10-00yi-0398000000-41c3a62b076046d87381Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, Negativesplash10-00di-0495000000-df406a9e4cc995523a7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, Negativesplash10-00dr-0592000000-928e66269ab2854faa42Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, Negativesplash10-00dr-0590000000-b364a55fc0598d9265b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, Negativesplash10-00dr-0890000000-b3a25d975f2a38d7e49fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, Negativesplash10-0079-0960000000-c67461d3bd965cbf289cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, Negativesplash10-000i-0920000000-830ad149a4fe8f36e211Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, Negativesplash10-07br-0910000000-35e5bd204c947e2c4bccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, Negativesplash10-05fs-0900000000-573b0c5a4593210b387aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00yi-0398000000-612bce8f105beae0c5f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0495000000-78584a9b664c5155b473Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0592000000-b37d658cf7b0d590aad4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0590000000-985f93ab468aa6a8a1b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0890000000-5757ca5e8720a47086dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0079-0960000000-c67461d3bd965cbf289cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0920000000-830ad149a4fe8f36e211Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-07br-0910000000-35e5bd204c947e2c4bccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-05fs-0900000000-573b0c5a4593210b387aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0294000000-9d89acbe9e631d718a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-31e36b1c042e1f53c0afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-2197000000-e7ed45d4821537db0598Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lmv-9110000000-b4cb6476f830b7047f38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-a8c5f8d16d784c75721aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kar-2159000000-92926ade35f53b386f30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9421000000-f62f4a6586c94d0d622eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00917
HMDB IDHMDB0001220
FooDB IDFDB022498
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35424
BioCyc ID5Z13E-15S-1115-DIHYDROXY-9-OXOPROS
METLIN ID6089
PDB IDNot Available
Wikipedia LinkProstaglandin_E2
Chemspider ID4444059
ChEBI ID15551
PubChem Compound ID5280360
Kegg Compound IDC00584
YMDB IDNot Available
ECMDB IDECMDB23855
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Corey, 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.
2. 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.
3. Corey, 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.
4. Ilzecka J: Prostaglandin E2 is increased in amyotrophic lateral sclerosis patients. Acta Neurol Scand. 2003 Aug;108(2):125-9.
5. Catanzarite VA: Prophylactic intramyometrial carboprost tromethamine does not substantially reduce blood loss relative to intramyometrial oxytocin at routine cesarean section. Am J Perinatol. 1990 Jan;7(1):39-42.
6. Waschbisch A, Fiebich BL, Akundi RS, Schmitz ML, Hoozemans JJ, Candelario-Jalil E, Virtainen N, Veerhuis R, Slawik H, Yrjanheikki J, Hull M: Interleukin-1 beta-induced expression of the prostaglandin E-receptor subtype EP3 in U373 astrocytoma cells depends on protein kinase C and nuclear factor-kappaB. J Neurochem. 2006 Feb;96(3):680-93. Epub 2006 Jan 9.
7. Seo JY, Kim EK, Lee SH, Park KC, Kim KH, Eun HC, Chung JH: Enhanced expression of cylooxygenase-2 by UV in aged human skin in vivo. Mech Ageing Dev. 2003 Aug-Sep;124(8-9):903-10.
8. Amato F, Rizzuto G, Nicoletti A, Senatore M, Roberti R: [Isolated peripheral arterial ischaemia and medullary neurostimulation: case report]. G Ital Nefrol. 2003 Mar-Apr;20(2):200-4.
9. Laitinen K, Arvola T, Moilanen E, Lampi AM, Ruuska T, Isolauri E: Characterization of breast milk received by infants with gross blood in stools. Biol Neonate. 2005;87(1):66-72. Epub 2004 Nov 9.
10. Yamada M, Ogata M, Kawai M, Mashima Y, Nishida T: Substance P in human tears. Cornea. 2003 Oct;22(7 Suppl):S48-54.
11. Choi SH, Langenbach R, Bosetti F: Cyclooxygenase-1 and -2 enzymes differentially regulate the brain upstream NF-kappa B pathway and downstream enzymes involved in prostaglandin biosynthesis. J Neurochem. 2006 Aug;98(3):801-11. Epub 2006 Jun 19.
12. Schmitz T, Dallot E, Leroy MJ, Breuiller-Fouche M, Ferre F, Cabrol D: EP(4) receptors mediate prostaglandin E(2)-stimulated glycosaminoglycan synthesis in human cervical fibroblasts in culture. Mol Hum Reprod. 2001 Apr;7(4):397-402.
13. Christidis N, Kopp S, Ernberg M: The effect on mechanical pain threshold over human muscles by oral administration of granisetron and diclofenac-sodium. Pain. 2005 Feb;113(3):265-70.
14. Konopka T, Rutkowska M, Hirnle L, Kopec W, Karolewska E: The secretion of prostaglandin E2 and interleukin 1-beta in women with periodontal diseases and preterm low-birth-weight. Bull Group Int Rech Sci Stomatol Odontol. 2003 Jan-Apr;45(1):18-28.
15. Iizuka H, Ohkawara A, Ishibashi Y: Human skin epidermal adenylate cyclase systems: defective beta-adrenergic responsiveness in the involved epidermis of Darier's disease. Curr Probl Dermatol. 1983;11:45-58.
16. Greaves MW: Does ultraviolet-evoked prostaglandin formation protect skin from actinic cancer? Lancet. 1978 Jan 28;1(8057):189.
17. 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.
18. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24501112
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=7224729
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=7836930