telaprevir   Click here for help

GtoPdb Ligand ID: 7871

Synonyms: VX-950
Compound class: Synthetic organic
Comment: Inhibits the hepatitis C viral enzyme NS3.4A serine protease but also has a recent repurposing claim for cathepsin A inhibition [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 4
Rotatable bonds 19
Topological polar surface area 179.56
Molecular weight 679.41
XLogP 3.05
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCC(C(=O)C(=O)NC1CC1)NC(=O)C1C2CCCC2CN1C(=O)C(C(C)(C)C)NC(=O)C(C1CCCCC1)NC(=O)c1nccnc1
Isomeric SMILES CCC[C@@H](C(=O)C(=O)NC1CC1)NC(=O)[C@@H]1[C@H]2CCC[C@H]2CN1C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](C1CCCCC1)NC(=O)c1nccnc1
InChI InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1
InChI Key BBAWEDCPNXPBQM-GDEBMMAJSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxamide
Synonyms Click here for help
VX-950
Database Links Click here for help
CAS Registry No. 402957-28-2 (source: Scifinder)
ChEBI CHEBI:68595
ChEMBL Ligand CHEMBL231813
DrugBank Ligand DB05521
DrugCentral Ligand 4173
GtoPdb PubChem SID 223366200
PubChem CID 3010818
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Tocris
Telaprevir
Cat. No. 6658