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(11R,16S)-misoprostol
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.

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05. Industrial Uses

			pharmaceutical [CHEBI:52217] (1978)

				drug [CHEBI:23888] (1930)

					oxytocic [CHEBI:36063] (8)

(11R,16S)-misoprostol [CHEBI:63695] (1)

					anti-ulcer drug [CHEBI:49201] (25)

(11R,16S)-misoprostol [CHEBI:63695] (1)

					reproductive control drug [CHEBI:50689] (25)

						abortifacient [CHEBI:50691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

08. Chemical Category

			main group molecular entity [CHEBI:33579] (25650)

					s-block molecular entity [CHEBI:33674] (7287)

							hydrogen molecular entity [CHEBI:33608] (6932)

								hydroxides [CHEBI:24651] (5641)

									organic hydroxy compound [CHEBI:33822] (3050)

alcohol [CHEBI:30879] (1371)

tertiary alcohol [CHEBI:26878] (183)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

secondary alcohol [CHEBI:35681] (342)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

					p-block molecular entity [CHEBI:33675] (25343)

						chalcogen molecular entity [CHEBI:33304] (15225)

								oxygen molecular entity [CHEBI:25806] (14414)

hydroxides [CHEBI:24651] (5641)

organic hydroxy compound [CHEBI:33822] (3050)

alcohol [CHEBI:30879] (1371)

tertiary alcohol [CHEBI:26878] (183)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

secondary alcohol [CHEBI:35681] (342)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

organooxygen compound [CHEBI:36963] (11352)

carbonyl compound [CHEBI:36586] (5928)

ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

beta-hydroxy ketone [CHEBI:55380] (18)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

carboxylic ester [CHEBI:33308] (1495)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

								organochalcogen compound [CHEBI:36962] (11874)

									organooxygen compound [CHEBI:36963] (11352)

carbonyl compound [CHEBI:36586] (5928)

ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

beta-hydroxy ketone [CHEBI:55380] (18)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

carboxylic ester [CHEBI:33308] (1495)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

						carbon group molecular entity [CHEBI:33582] (23847)

							organic molecular entity [CHEBI:50860] (23769)

								heteroorganic entity [CHEBI:33285] (15197)

organochalcogen compound [CHEBI:36962] (11874)

organooxygen compound [CHEBI:36963] (11352)

carbonyl compound [CHEBI:36586] (5928)

ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

beta-hydroxy ketone [CHEBI:55380] (18)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

carboxylic ester [CHEBI:33308] (1495)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

								organic hydroxy compound [CHEBI:33822] (3050)

alcohol [CHEBI:30879] (1371)

tertiary alcohol [CHEBI:26878] (183)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

secondary alcohol [CHEBI:35681] (342)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

								ester [CHEBI:35701] (3370)

carboxylic ester [CHEBI:33308] (1495)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

								organic molecule [CHEBI:72695] (11399)

									organic oxo compound [CHEBI:36587] (5932)

carbonyl compound [CHEBI:36586] (5928)

ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

beta-hydroxy ketone [CHEBI:55380] (18)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

carboxylic ester [CHEBI:33308] (1495)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

			polyatomic entity [CHEBI:36357] (18777)

				molecule [CHEBI:25367] (11520)

						organic molecule [CHEBI:72695] (11399)

							organic oxo compound [CHEBI:36587] (5932)

								carbonyl compound [CHEBI:36586] (5928)

									ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

beta-hydroxy ketone [CHEBI:55380] (18)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

									carboxylic ester [CHEBI:33308] (1495)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

				heteroatomic molecular entity [CHEBI:37577] (13672)

					hydroxides [CHEBI:24651] (5641)

						organic hydroxy compound [CHEBI:33822] (3050)

							alcohol [CHEBI:30879] (1371)

								tertiary alcohol [CHEBI:26878] (183)

methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

								secondary alcohol [CHEBI:35681] (342)

									methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate [CHEBI:63691] (5)

(11R,16S)-misoprostol [CHEBI:63695] (1)

ChEBI Compound Accession Identifier:

[CHEBI:63695]

ChEBI Compound Description:

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.

ChEBI Compound Identification Number:

63695

ChEBI InChI Value:

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

ChEBI InChIKey Value:

OJLOPKGSLYJEMD-YCVNZHGXSA-N

ChEBI Compound Name:

(11R,16S)-misoprostol

ChEBI SMILES Value:

CCCC[C@](C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC

ChEBI Substance ID:

135611152

ChEBI URL:

ChEBI:63695

ChemSpider ID:

8061946

Ontomatica Chemical Accession Key (OnChAKey):

OJLOPKGSLYJEMD_YCVNZHGXSA_N_000_000000

PubChem Compound ID:

9886273