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CHEBI:15553 - prostaglandin F

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ChEBI Name prostaglandin F
ChEBI ID CHEBI:15553
ChEBI ASCII Name prostaglandin F2alpha
Definition A prostaglandins Fα that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:10913, CHEBI:8516, CHEBI:26327
Supplier Information
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Formula C20H34O5
Net Charge 0
Average Mass 354.48100
Monoisotopic Mass 354.241
InChI InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChIKey PXGPLTODNUVGFL-YNNPMVKQSA-N
SMILES CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:10090) See: MetaboLights Study
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing prostaglandin F (CHEBI:15553) has role human metabolite (CHEBI:77746)
prostaglandin F (CHEBI:15553) has role mouse metabolite (CHEBI:75771)
prostaglandin F (CHEBI:15553) is a monocarboxylic acid (CHEBI:25384)
prostaglandin F (CHEBI:15553) is a prostaglandins Fα (CHEBI:36066)
prostaglandin F (CHEBI:15553) is conjugate acid of prostaglandin F(1−) (CHEBI:57404)
Incoming 11-epi-prostaglandin F (CHEBI:27595) has functional parent prostaglandin F (CHEBI:15553)
13,14-dihydro-15-keto-PGF (CHEBI:63976) has functional parent prostaglandin F (CHEBI:15553)
13,14-dihydroprostaglandin F (CHEBI:88346) has functional parent prostaglandin F (CHEBI:15553)
15-oxo-prostaglandin F (CHEBI:28442) has functional parent prostaglandin F (CHEBI:15553)
8-epi-prostaglandin F (CHEBI:34505) has functional parent prostaglandin F (CHEBI:15553)
carboprost (CHEBI:3403) has functional parent prostaglandin F (CHEBI:15553)
prostaglandin F 1-ethanolamide (CHEBI:53081) has functional parent prostaglandin F (CHEBI:15553)
prostaglandin F 1-glyceryl ester (CHEBI:90233) has functional parent prostaglandin F (CHEBI:15553)
prostaglandin F dimethylamine (CHEBI:73741) has functional parent prostaglandin F (CHEBI:15553)
tafluprost (CHEBI:66899) has functional parent prostaglandin F (CHEBI:15553)
2,3-dinor-8-epi-prostaglandin F (CHEBI:34230) is a prostaglandin F (CHEBI:15553)
prostaglandin F(1−) (CHEBI:57404) is conjugate base of prostaglandin F (CHEBI:15553)
IUPAC Name
(5Z,13E,15S)-9α,11α,15-trihydroxyprosta-5,13-dien-1-oic acid
INNs Sources
dinoprost ChemIDplus
dinoprosta ChemIDplus
dinoprostum ChemIDplus
Synonyms Sources
(+)-Prostaglandin F2a KEGG COMPOUND
(5Z,13E)-(15S)-9alpha,11alpha,15-Trihydroxyprosta-5,13-dienoate KEGG COMPOUND
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid KEGG COMPOUND
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-oic acid KEGG COMPOUND
9a,11a-PGF2 KEGG COMPOUND
Amoglandin KEGG COMPOUND
Cyclosin KEGG COMPOUND
Dinoprost KEGG COMPOUND
Enzaprost KEGG COMPOUND
Enzaprost F KEGG COMPOUND
l-PGF2-alpha ChemIDplus
l-Prostaglandin F2-alpha ChemIDplus
Panacelan KEGG COMPOUND
PGF2a KEGG COMPOUND
PGF ChEBI
Prostaglandin F2a KEGG COMPOUND
Prostaglandin F2alpha KEGG COMPOUND
Prostin F 2 alpha KEGG COMPOUND
Protamodin KEGG COMPOUND
U 14583 KEGG COMPOUND
Database Links Databases
5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY MetaCyc
C00639 KEGG COMPOUND
D00081 KEGG DRUG
Dinoprost Wikipedia
HMDB01139 HMDB
LMFA03010002 LIPID MAPS
View more database links
Registry Numbers Types Sources
2225571 Beilstein Registry Number Beilstein
2225571 Reaxys Registry Number Reaxys
551-11-1 CAS Registry Number KEGG COMPOUND
551-11-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11438482 PubMed citation Europe PMC
23807981 PubMed citation Europe PMC
Last Modified
07 June 2016