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CHEBI:15551 - prostaglandin E2

ChEBI IDCHEBI:15551
ChEBI Nameprostaglandin E2
Stars
ASCII Nameprostaglandin E2
DefinitionProstaglandin 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.
Secondary ChEBI IDsCHEBI:4625, CHEBI:8512, CHEBI:10910, CHEBI:10911, CHEBI:26323, CHEBI:114125
Last Modified9 June 2021
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC20H32O5
Net Charge0
Average Mass352.471
Monoisotopic Mass352.22497
SMILESCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O
InChIInChI=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
InChIKeyXEYBRNLFEZDVAW-ARSRFYASSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Mus musculus (ncbitaxon:10090)
- MetaboLights (MTBLS143)
- PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application:
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).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
dinoprostonaWHO MedNet
dinoprostoneWHO MedNet
dinoprostoneWHO MedNet
dinoprostonumWHO MedNet
Synonyms  Source
Prostaglandin E2KEGG COMPOUND
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoateKEGG COMPOUND
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoateKEGG COMPOUND
PGE2ChemIDplus
U-12,062ChemIDplus
(15S)-prostaglandin E2ChemIDplus
Brand Names  Source
CervidilKEGG DRUG
PrepidilKEGG DRUG
Prostin E2KEGG DRUG
PropessDrugBank
ProstinChemIDplus
Glandin-E2ChEBI
Manual XrefsDatabases
C00584KEGG COMPOUND
LMFA03010003LIPID MAPS
D00079KEGG DRUG
DB00917DrugBank
GB851827Patent
US3598858Patent
DE2011969Patent
NL6505799Patent
Prostaglandin_E2Wikipedia
LSM-42919LINCS
HMDB0001220HMDB
FDB022498FooDB
913DrugCentral
P2EPDBeChem
Registry NumbersSources
Beilstein:2224724Beilstein
Reaxys:2224724Reaxys
CAS:363-24-6KEGG COMPOUND
CAS:363-24-6ChemIDplus
Citations