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etilefrine   Click here for help

GtoPdb Ligand ID: 14324

Synonyms: Effortil® | ethylnorphenylephrine | ethylphenephrine
Approved drug
etilefrine is an approved drug
Compound class: Synthetic organic
Comment: Etilefrine is a sympathomimetic, non-selective α1-adrenoceptor agonist [2,4,7].
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 3
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 52.49
Molecular weight 181.23
XLogP 0.02
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 CCNCC(C1=CC=CC(=C1)O)O
Isomeric SMILES CCNCC(C1=CC(=CC=C1)O)O
InChI InChI=1S/C10H15NO2/c1-2-11-7-10(13)8-4-3-5-9(12)6-8/h3-6,10-13H,2,7H2,1H3
InChI Key SQVIAVUSQAWMKL-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.
IUPAC Name Click here for help
3-[2-(ethylamino)-1-hydroxyethyl]phenol
International Nonproprietary Names Click here for help
INN number INN
2229 etilefrine
Synonyms Click here for help
Effortil® | ethylnorphenylephrine | ethylphenephrine
Database Links Click here for help
BindingDB Ligand 97154
CAS Registry No. 709-55-7 (source: WHO INN record)
ChEBI CHEBI:91518
ChEMBL Ligand CHEMBL86882
DrugBank Ligand DB08985
PubChem CID 3306
Search Google for chemical match using the InChIKey SQVIAVUSQAWMKL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone SQVIAVUSQAWMKL
Search PubMed clinical trials etilefrine
Search PubMed titles etilefrine
Search PubMed titles/abstracts etilefrine
UniChem Compound Search for chemical match using the InChIKey SQVIAVUSQAWMKL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey SQVIAVUSQAWMKL-UHFFFAOYSA-N