CHEBI:63695 - (11R,16S)-misoprostol

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ChEBI Name (11R,16S)-misoprostol
ChEBI ID CHEBI:63695
ChEBI ASCII Name (11R,16S)-misoprostol
Definition A methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate that has 8S,11S,12S,16R-configuration. It is the pharmacologically active diastereoisomeric component of misoprostol.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H38O5
Net Charge 0
Average Mass 382.53410
Monoisotopic Mass 382.27192
InChI InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22+/m1/s1
InChIKey OJLOPKGSLYJEMD-YCVNZHGXSA-N
SMILES CCCC[C@](C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
Roles Classification
Application(s): anti-ulcer drug
One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
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).
abortifacient
A chemical substance that interrupts pregnancy after implantation.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (11R,16S)-misoprostol (CHEBI:63695) has role abortifacient (CHEBI:50691)
(11R,16S)-misoprostol (CHEBI:63695) has role anti-ulcer drug (CHEBI:49201)
(11R,16S)-misoprostol (CHEBI:63695) has role oxytocic (CHEBI:36063)
(11R,16S)-misoprostol (CHEBI:63695) is a methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate (CHEBI:63691)
(11R,16S)-misoprostol (CHEBI:63695) is enantiomer of (11S,16R)-misoprostol (CHEBI:63698)
Incoming misoprostol (CHEBI:63610) has part (11R,16S)-misoprostol (CHEBI:63695)
(11S,16R)-misoprostol (CHEBI:63698) is enantiomer of (11R,16S)-misoprostol (CHEBI:63695)
IUPAC Name
methyl (11α,13E,16S)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate
Synonyms Sources
(16S)-15-deoxy--16-hydroxy-16-methyl-PGE1 methyl ester ChEBI
methyl 11R,16S-dihydroxy-16-methyl-9-oxoprost-13E-en-1-oate ChEBI
Registry Number Type Source
6092906 Reaxys Registry Number Reaxys
Last Modified
20 January 2012