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CHEBI:3403 - carboprost

ChEBI IDCHEBI:3403
ChEBI Namecarboprost
Stars
DefinitionProstaglandin F2α in which the hydrogen at position 15 is substituted by methyl (S configuration). It is used as an abortifacient agent that is effective in both the first and second trimesters of pregnancy.
Last Modified23 November 2020
DownloadsMolfile
FormulaC21H36O5
Net Charge0
Average Mass368.514
Monoisotopic Mass368.25627
SMILESCCCCC[C@](C)(O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@@H](O)C[C@H]1O
InChIInChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1
InChIKeyDLJKPYFALUEJCK-IIELGFQLSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Applications:
abortifacient  A chemical substance that interrupts pregnancy after implantation.
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)
carboprost (CHEBI:3403) has functional parent prostaglandin F2α (CHEBI:15553)
carboprost (CHEBI:3403) has role abortifacient (CHEBI:50691)
carboprost (CHEBI:3403) has role oxytocic (CHEBI:36063)
carboprost (CHEBI:3403) is a hydroxy monocarboxylic acid (CHEBI:35868)
carboprost (CHEBI:3403) is conjugate acid of carboprost(1−) (CHEBI:59205)
Incoming Relation(s)
carboprost(1−) (CHEBI:59205) is conjugate base of carboprost (CHEBI:3403)
IUPAC Name 
(5Z,13E,15S)-9α,11α,15-trihydroxy-15-methylprosta-5,13-dien-1-oic acid
INNs  Source
carboprostWHO MedNet
carboprostWHO MedNet
carboprostumWHO MedNet
carboprostWHO MedNet
Synonyms  Source
(15S)-15-methyl-PGF2αChemIDplus
(15S)-15-methylprostaglandin F2αChemIDplus
15(S)-15-methyl-PGF2αChemIDplus
15(S)-15-methylprostaglandin F2αChemIDplus
Manual XrefsDatabases
C06872KEGG COMPOUND
DB00429DrugBank
D02343KEGG DRUG
DE2121980Patent
US3728382Patent
502DrugCentral
CarboprostWikipedia
4444532ChemSpider
Registry NumbersSources
Beilstein:2949991Beilstein
CAS:35700-23-3KEGG COMPOUND
CAS:35700-23-3ChemIDplus
Citations