sofosbuvir   Click here for help

GtoPdb Ligand ID: 7368

Synonyms: GI-7977 | PSI 7977 | Sovaldi®
Approved drug PDB Ligand
sofosbuvir is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Sofosbuvir is a nucleotide analogue whose action inhibits hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase. It acts as a chain terminator to limit viral RNA replication.
Sofosbuvir is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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 9
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 167.99
Molecular weight 529.16
XLogP 1.93
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 CC(OC(=O)C(NP(=O)(Oc1ccccc1)OCC1OC(C(C1O)(C)F)n1ccc(=O)[nH]c1=O)C)C
Isomeric SMILES CC(OC(=O)[C@@H](N[P@@](=O)(Oc1ccccc1)OC[C@H]1O[C@H]([C@]([C@@H]1O)(C)F)n1ccc(=O)[nH]c1=O)C)C
InChI InChI=1S/C22H29FN3O9P/c1-13(2)33-19(29)14(3)25-36(31,35-15-8-6-5-7-9-15)32-12-16-18(28)22(4,23)20(34-16)26-11-10-17(27)24-21(26)30/h5-11,13-14,16,18,20,28H,12H2,1-4H3,(H,25,31)(H,24,27,30)/t14-,16+,18+,20+,22+,36-/m0/s1
InChI Key TTZHDVOVKQGIBA-IQWMDFIBSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
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.
IUPAC Name Click here for help
propan-2-yl (2S)-2-[[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
International Nonproprietary Names Click here for help
INN number INN
9665 sofosbuvir
Synonyms Click here for help
GI-7977 | PSI 7977 | Sovaldi®
Database Links Click here for help
CAS Registry No. 1190307-88-0 (source: Scifinder)
ChEMBL Ligand CHEMBL1259059
DrugBank Ligand DB08934
DrugCentral Ligand 4811
GtoPdb PubChem SID 178103940
PubChem CID 45375808
RCSB PDB Ligand WG6
Search Google for chemical match using the InChIKey TTZHDVOVKQGIBA-IQWMDFIBSA-N
Search Google for chemicals with the same backbone TTZHDVOVKQGIBA
Search PubMed clinical trials sofosbuvir
Search PubMed titles sofosbuvir
Search PubMed titles/abstracts sofosbuvir
UniChem Compound Search for chemical match using the InChIKey TTZHDVOVKQGIBA-IQWMDFIBSA-N
UniChem Connectivity Search for chemical match using the InChIKey TTZHDVOVKQGIBA-IQWMDFIBSA-N
Wikipedia Sofosbuvir