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.
2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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
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UniChem Compound Search for chemical match using the InChIKey WXXSNCNJFUAIDG-UHFFFAOYSA-N
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Wikipedia Riociguat