isosorbide mononitrate   Click here for help

GtoPdb Ligand ID: 7052

Synonyms: AHR-4698 | BM-22-145 | Imdur® | IS-5-MN | ISMN | Monosorb®
Approved drug
isosorbide mononitrate is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Isosorbide mononitrate is termed a nitrate drug and acts as a vasodilator. It is similar to nitroglycerin, but is slower to act.
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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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 91.06
Molecular weight 191.04
XLogP -0.91
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES [O-][N+](=O)OC1COC2C1OCC2O
Isomeric SMILES [O-][N+](=O)O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2O
InChI InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1
InChI Key YWXYYJSYQOXTPL-SLPGGIOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1991))
IUPAC Name Click here for help
[(3R,3aS,6S,6aR)-6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl] nitrate
International Nonproprietary Names Click here for help
INN number INN
5177 isosorbide mononitrate
Synonyms Click here for help
AHR-4698 | BM-22-145 | Imdur® | IS-5-MN | ISMN | Monosorb®
Database Links Click here for help
CAS Registry No. 16051-77-7
ChEMBL Ligand CHEMBL1311
DrugBank Ligand DB01020
DrugCentral Ligand 1506
GtoPdb PubChem SID 178103631
PubChem CID 27661
Search Google for chemical match using the InChIKey YWXYYJSYQOXTPL-SLPGGIOYSA-N
Search Google for chemicals with the same backbone YWXYYJSYQOXTPL
Search PubMed clinical trials isosorbide mononitrate
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UniChem Compound Search for chemical match using the InChIKey YWXYYJSYQOXTPL-SLPGGIOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YWXYYJSYQOXTPL-SLPGGIOYSA-N
Wikipedia Isosorbide mononitrate