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

Default Structure
ChEBI IDCHEBI:63695
ChEBI Name(11R,16S)-misoprostol
Stars
ASCII Name(11R,16S)-misoprostol
DefinitionA 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.
Last Modified20 January 2012
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H38O5
Net Charge0
Average Mass382.541
Monoisotopic Mass382.27192
SMILESCCCC[C@](C)(O)C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
InChIInChI=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
InChIKeyOJLOPKGSLYJEMD-YCVNZHGXSA-N
Roles Classification
Applications:
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.
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.
ChEBI Ontology
Outgoing Relation(s)
(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 Relation(s)
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  Source
(16S)-15-deoxy--16-hydroxy-16-methyl-PGE1 methyl esterChEBI
methyl 11R,16S-dihydroxy-16-methyl-9-oxoprost-13E-en-1-oateChEBI
Registry NumbersSources
Reaxys:6092906Reaxys