celiprolol   Click here for help

GtoPdb Ligand ID: 9064

Synonyms: Celectol® | REV 5320 | Selectol® | ST-1396 | ST1396
Approved drug
celiprolol is an approved drug (UK (2009))
Compound class: Synthetic organic
Comment: Celiprolol is a cardioselective β1-adrenoceptor antagonist, but also displays weak partial agonist (sympathomimetic) action at β2-adrenoceptors.
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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 6
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 90.9
Molecular weight 379.25
XLogP 1.94
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCN(C(=O)Nc1ccc(c(c1)C(=O)C)OCC(CNC(C)(C)C)O)CC
Isomeric SMILES CCN(C(=O)Nc1ccc(c(c1)C(=O)C)OCC(CNC(C)(C)C)O)CC
InChI InChI=1S/C20H33N3O4/c1-7-23(8-2)19(26)22-15-9-10-18(17(11-15)14(3)24)27-13-16(25)12-21-20(4,5)6/h9-11,16,21,25H,7-8,12-13H2,1-6H3,(H,22,26)
InChI Key JOATXPAWOHTVSZ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (UK (2009))
IUPAC Name Click here for help
3-[3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1,1-diethylurea
International Nonproprietary Names Click here for help
INN number INN
3979 celiprolol
Synonyms Click here for help
Celectol® | REV 5320 | Selectol® | ST-1396 | ST1396
Database Links Click here for help
CAS Registry No. 56980-93-9 (source: PubChem)
ChEMBL Ligand CHEMBL27810
DrugBank Ligand DB04846
DrugCentral Ligand 569
GtoPdb PubChem SID 315661149
PubChem CID 2663
Search Google for chemical match using the InChIKey JOATXPAWOHTVSZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JOATXPAWOHTVSZ
Search PubMed clinical trials celiprolol
Search PubMed titles celiprolol
Search PubMed titles/abstracts celiprolol
UniChem Compound Search for chemical match using the InChIKey JOATXPAWOHTVSZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JOATXPAWOHTVSZ-UHFFFAOYSA-N
Wikipedia Celiprolol