aliskiren   Click here for help

GtoPdb Ligand ID: 4812

Synonyms: CGP-060536B | SPP100 | Tekturna®
Approved drug PDB Ligand
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: aliskiren

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 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
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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 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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2007))
IUPAC Name Click here for help
(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 Click here for help
INN number INN
7992 aliskiren
Synonyms Click here for help
CGP-060536B | SPP100 | Tekturna®
Database Links Click here for help
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
Search Google for chemicals with the same backbone UXOWGYHJODZGMF
Search PubMed clinical trials aliskiren
Search PubMed titles aliskiren
Search PubMed titles/abstracts aliskiren
SynPHARM 78508 (in complex with renin)
UniChem Compound Search for chemical match using the InChIKey UXOWGYHJODZGMF-QORCZRPOSA-N
UniChem Connectivity Search for chemical match using the InChIKey UXOWGYHJODZGMF-QORCZRPOSA-N
Wikipedia Aliskiren