aliskiren   

GtoPdb Ligand ID: 4812

Synonyms: CGP-060536B | SPP100 | Tekturna®
aliskiren is an approved drug (EMA & FDA (2007))
Compound class: Synthetic organic
Comment: Aliskiren is the first in class renin inhibitor. The Tekturna trade name refers to the hemi-fumarate: (PubChem CID 6918427). Ligand structure in PDB (see link)
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 20
Topological polar surface area 146.13
Molecular weight 551.39
XLogP 3.27
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COCCCOc1cc(ccc1OC)CC(C(C)C)CC(C(CC(C(=O)NCC(C(=O)N)(C)C)C(C)C)O)N
Isomeric SMILES COCCCOc1cc(ccc1OC)C[C@H](C(C)C)C[C@@H]([C@H](C[C@H](C(=O)NCC(C(=O)N)(C)C)C(C)C)O)N
InChI InChI=1S/C30H53N3O6/c1-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36/h10-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35)/t22-,23-,24-,25-/m0/s1
InChI Key UXOWGYHJODZGMF-QORCZRPOSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2007))
IUPAC Name
(2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-2-(propan-2-yl)nonanamide
International Nonproprietary Names
INN number INN
7992 aliskiren
Synonyms
CGP-060536B | SPP100 | Tekturna®
Database Links
CAS Registry No. 173334-57-1 (source: Scifinder)
ChEBI CHEBI:601027
ChEMBL Ligand CHEMBL1639
DrugBank Ligand DB01258
DrugCentral Ligand 119
GtoPdb PubChem SID 178101514
PubChem CID 5493444
RCSB PDB Ligand C41
Search Google for chemical match using the InChIKey UXOWGYHJODZGMF-QORCZRPOSA-N
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Search UniChem for chemical match using the InChIKey UXOWGYHJODZGMF-QORCZRPOSA-N
Search UniChem for chemicals with the same backbone UXOWGYHJODZGMF
SynPHARM 78508 (in complex with renin)
Wikipedia Aliskiren