CHEBI:15551 - prostaglandin E2

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name prostaglandin E2
ChEBI ID CHEBI:15551
ChEBI ASCII Name prostaglandin E2
Definition Prostaglandin F2α in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:26323, CHEBI:10910, CHEBI:10911, CHEBI:4625, CHEBI:114125, CHEBI:8512
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C20H32O5
Net Charge 0
Average Mass 352.471
Monoisotopic Mass 352.22497
InChI 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
InChIKey XEYBRNLFEZDVAW-ARSRFYASSA-N
SMILES CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: MetaboLights Study
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Application(s): oxytocic
A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing prostaglandin E2 (CHEBI:15551) has role human metabolite (CHEBI:77746)
prostaglandin E2 (CHEBI:15551) has role mouse metabolite (CHEBI:75771)
prostaglandin E2 (CHEBI:15551) has role oxytocic (CHEBI:36063)
prostaglandin E2 (CHEBI:15551) is a prostaglandins E (CHEBI:26338)
prostaglandin E2 (CHEBI:15551) is conjugate acid of prostaglandin E2(1−) (CHEBI:606564)
Incoming 13,14-dihydro-15-oxo-prostaglandin E2 (CHEBI:15550) has functional parent prostaglandin E2 (CHEBI:15551)
15-dehydro-prostaglandin E2 (CHEBI:15547) has functional parent prostaglandin E2 (CHEBI:15551)
2-[(5Z,13E,15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dien-1-oyl]-sn-glycero-3-phosphocholine (CHEBI:137585) has functional parent prostaglandin E2 (CHEBI:15551)
2-[(5Z,13E,15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dien-1-oyl]-sn-glycero-3-phosphoethanolamine (CHEBI:138361) has functional parent prostaglandin E2 (CHEBI:15551)
20-hydroxyprostaglandin E2 (CHEBI:137370) has functional parent prostaglandin E2 (CHEBI:15551)
8-epi-prostaglandin E2 (CHEBI:131888) has functional parent prostaglandin E2 (CHEBI:15551)
nitroproston (CHEBI:142127) has functional parent prostaglandin E2 (CHEBI:15551)
prostaglandin E2 1-glyceryl ester (CHEBI:90230) has functional parent prostaglandin E2 (CHEBI:15551)
prostaglandin E2 2-glyceryl ester (CHEBI:137172) has functional parent prostaglandin E2 (CHEBI:15551)
prostaglandin E2(1−) (CHEBI:606564) is conjugate base of prostaglandin E2 (CHEBI:15551)
IUPAC Name
(5Z,13E,15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
INNs Sources
dinoprostona WHO MedNet
dinoprostone WHO MedNet
dinoprostone WHO MedNet
dinoprostonum WHO MedNet
Synonyms Sources
(15S)-prostaglandin E2 ChemIDplus
(5Z,11α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid ChemIDplus
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate KEGG COMPOUND
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate KEGG COMPOUND
(E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid ChemIDplus
(Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid ChEMBL
Dinoproston ChemIDplus
PGE2 ChemIDplus
PGE2 KEGG COMPOUND
Prostaglandin E2 KEGG COMPOUND
U 12062 ChemIDplus
U-12,062 ChemIDplus
U-12062 ChemIDplus
Brand Names Sources
Cervidil KEGG DRUG
Cerviprime ChemIDplus
Cerviprost ChemIDplus
Enzaprost E ChemIDplus
Glandin-E2 ChEBI
Minprositin E2 ChemIDplus
Minprostin E2 ChemIDplus
Prepidil KEGG DRUG
Propess DrugBank
Prostarmon E ChemIDplus
Prostenone ChemIDplus
Prostin ChemIDplus
Prostin E2 KEGG DRUG
Manual Xrefs Databases
913 DrugCentral
C00584 KEGG COMPOUND
D00079 KEGG DRUG
DB00917 DrugBank
DE2011969 Patent
FDB022498 FooDB
GB851827 Patent
HMDB0001220 HMDB
LMFA03010003 LIPID MAPS
LSM-42919 LINCS
NL6505799 Patent
P2E PDBeChem
Prostaglandin_E2 Wikipedia
US3598858 Patent
View more database links
Registry Numbers Types Sources
2224724 Beilstein Registry Number Beilstein
2224724 Reaxys Registry Number Reaxys
363-24-6 CAS Registry Number KEGG COMPOUND
363-24-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11279302 PubMed citation Europe PMC
12746806 PubMed citation Europe PMC
12859290 PubMed citation Europe PMC
14499495 PubMed citation Europe PMC
14535055 PubMed citation Europe PMC
14703707 PubMed citation Europe PMC
15542928 PubMed citation Europe PMC
15661432 PubMed citation Europe PMC
16405508 PubMed citation Europe PMC
16787416 PubMed citation Europe PMC
16978535 PubMed citation Europe PMC
20671299 PubMed citation Europe PMC
2403792 PubMed citation Europe PMC
24501112 PubMed citation Europe PMC
32898608 PubMed citation Europe PMC
33271839 PubMed citation Europe PMC
33559528 PubMed citation Europe PMC
33685091 PubMed citation Europe PMC
33715333 PubMed citation Europe PMC
33782420 PubMed citation Europe PMC
33811074 PubMed citation Europe PMC
33958485 PubMed citation Europe PMC
34065827 PubMed citation Europe PMC
34071686 PubMed citation Europe PMC
34102274 PubMed citation Europe PMC
6317292 PubMed citation Europe PMC
7224729 PubMed citation Europe PMC
74611 PubMed citation Europe PMC
7836930 PubMed citation Europe PMC
9276764 PubMed citation Europe PMC
Last Modified
09 June 2021