misoprostol (methyl ester)   Click here for help

GtoPdb Ligand ID: 1936

Synonyms: Arthrotec® | BRN 4155643 | CCRIS 6859 | Cytotec® | HSDB 3573 | SC 29333
Approved drug
misoprostol (methyl ester) is an approved drug (FDA (1988))
Compound class: Synthetic organic
Comment: The INN-assigned approved drug misoprostol is a racemic mixture of two epimers and their enantiomers. For more information, please see the ChEBI link above. Note that the INN-assigned structure represents the methyl ester form of the compound as which the drug is administered. The drug is then converted in vivo to the active metabolite misoprostol (free acid form).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: misoprostol

misoprostol (methyl ester) is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 83.83
Molecular weight 382.27
XLogP 3.57
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCCC(CC=CC1C(O)CC(=O)C1CCCCCCC(=O)OC)(O)C
Isomeric SMILES CCCCC(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC)(O)C
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
InChI Key OJLOPKGSLYJEMD-URPKTTJQSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1988))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Is prodrug? Yes
Active form misoprostol (free acid form)
IUPAC Name Click here for help
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
International Nonproprietary Names Click here for help
INN number INN
5154 misoprostol
Synonyms Click here for help
Arthrotec® | BRN 4155643 | CCRIS 6859 | Cytotec® | HSDB 3573 | SC 29333
Database Links Click here for help
Specialist databases
GPCRdb Ligand misoprostol (methyl ester)
Other databases
CAS Registry No. 59122-46-2 (source: Scifinder)
ChEBI CHEBI:63610
ChEMBL Ligand CHEMBL606
DrugBank Ligand DB00929
DrugCentral Ligand 1817
GtoPdb PubChem SID 135650611
PubChem CID 5282381
Search Google for chemical match using the InChIKey OJLOPKGSLYJEMD-URPKTTJQSA-N
Search Google for chemicals with the same backbone OJLOPKGSLYJEMD
Search PubMed clinical trials misoprostol
Search PubMed titles misoprostol
Search PubMed titles/abstracts misoprostol
UniChem Compound Search for chemical match using the InChIKey OJLOPKGSLYJEMD-URPKTTJQSA-N
UniChem Connectivity Search for chemical match using the InChIKey OJLOPKGSLYJEMD-URPKTTJQSA-N
Wikipedia Misoprostol

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Tocris
Misoprostol (links to external site)
Cat. No. 2297