riociguat   Click here for help

GtoPdb Ligand ID: 5257

Synonyms: Adempas® | BAY 63-2521
Approved drug PDB Ligand
riociguat is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Riociguat is the first-in-class stimulator of soluble guanylate cyclase (sGC) class of drugs.

riociguat 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 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 9
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 138.07
Molecular weight 422.16
XLogP 2.34
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 COC(=O)N(c1c(N)nc(nc1N)c1nn(c2c1cccn2)Cc1ccccc1F)C
Isomeric SMILES COC(=O)N(c1c(N)nc(nc1N)c1nn(c2c1cccn2)Cc1ccccc1F)C
InChI InChI=1S/C20H19FN8O2/c1-28(20(30)31-2)15-16(22)25-18(26-17(15)23)14-12-7-5-9-24-19(12)29(27-14)10-11-6-3-4-8-13(11)21/h3-9H,10H2,1-2H3,(H4,22,23,25,26)
InChI Key WXXSNCNJFUAIDG-UHFFFAOYSA-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 (2013)  |  EMA (2014)
IUPAC Name Click here for help
methyl N-(4,6-diamino-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-5-yl)-N-methylcarbamate
International Nonproprietary Names Click here for help
INN number INN
8857 riociguat
Synonyms Click here for help
Adempas® | BAY 63-2521
Database Links Click here for help
CAS Registry No. 625115-55-1
ChEBI CHEBI:76018
ChEMBL Ligand CHEMBL2107834
DrugCentral Ligand 4807
GtoPdb PubChem SID 178101941
PubChem CID 11304743
RCSB PDB Ligand GZO
Search Google for chemical match using the InChIKey WXXSNCNJFUAIDG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WXXSNCNJFUAIDG
Search PubMed clinical trials riociguat
Search PubMed titles riociguat
Search PubMed titles/abstracts riociguat
UniChem Compound Search for chemical match using the InChIKey WXXSNCNJFUAIDG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey WXXSNCNJFUAIDG-UHFFFAOYSA-N
Wikipedia Riociguat

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MedChemExpress
Riociguat (links to external site)
Cat. No. HY-14779