sacubitril   Click here for help

GtoPdb Ligand ID: 7857

Synonyms: AHU377 | Entresto® | Neparvis®
Approved drug
sacubitril is an approved drug (EMA & FDA (2015))
Compound class: Synthetic organic
Comment: Sacubitril is a prodrug activated by de-ethylation via esterases to the neprilysin inhibitor sacubitrilat. Neprilysin is also known as neutral endopeptidase (NEP), and its official gene symbol is MME (membrane metallo-endopeptidase ). The chemical database relationships are detailed in this blogpost. Sabucatril is a component of the approved fixed mixture Entresto®, previously known as LCZ696, and which is now approved for heart failure (see Clinical data tab).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 13
Topological polar surface area 92.7
Molecular weight 411.2
XLogP 3.86
No. Lipinski's rules broken 1
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Canonical SMILES CCOC(=O)C(CC(Cc1ccc(cc1)c1ccccc1)NC(=O)CCC(=O)O)C
Isomeric SMILES CCOC(=O)[C@@H](C[C@@H](Cc1ccc(cc1)c1ccccc1)NC(=O)CCC(=O)O)C
InChI InChI=1S/C24H29NO5/c1-3-30-24(29)17(2)15-21(25-22(26)13-14-23(27)28)16-18-9-11-20(12-10-18)19-7-5-4-6-8-19/h4-12,17,21H,3,13-16H2,1-2H3,(H,25,26)(H,27,28)/t17-,21+/m1/s1