CHEBI:15551 - prostaglandin E2

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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
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Formula C20H32O5
Net Charge 0
Average Mass 352.46510
Monoisotopic Mass 352.225
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).
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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 ChemIDplus
dinoprostone KEGG DRUG
dinoprostonum ChemIDplus
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
Dinoprostone KEGG COMPOUND
PGE2 ChemIDplus
PGE2 KEGG COMPOUND
Prostaglandin E2 KEGG COMPOUND
Brand Names Sources
Prepidil KEGG DRUG
Propess DrugBank
Prostin E2 KEGG DRUG
Manual Xrefs Databases
5Z13E-15S-1115-DIHYDROXY-9-OXOPROS MetaCyc
913 DrugCentral
C00584 KEGG COMPOUND
D00079 KEGG DRUG
DB00917 DrugBank
DE2011969 Patent
GB851827 Patent
HMDB0001220 HMDB
LMFA03010003 LIPID MAPS
NL6505799 Patent
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
24501112 PubMed citation Europe PMC
7224729 PubMed citation Europe PMC
7836930 PubMed citation Europe PMC
Last Modified
12 September 2018