phenacetin   Click here for help

GtoPdb Ligand ID: 7402

Synonyms: acetophenetidin
Approved drug PDB Ligand
phenacetin is an approved drug
Compound class: Synthetic organic
Comment: This drug is rapidly metabolised to paracetamol, (aka acetaminophen), so it is conceivable that some of its therapeutic activity is attributable this major metabolite.
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 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 38.33
Molecular weight 179.09
XLogP 1.61
No. Lipinski's rules broken 0
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 CCOc1ccc(cc1)NC(=O)C
Isomeric SMILES CCOc1ccc(cc1)NC(=O)C
InChI InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
InChI Key CPJSUEIXXCENMM-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
Withdrawn drug? Yes
IUPAC Name Click here for help
N-(4-Ethoxyphenyl)acetamide
International Nonproprietary Names Click here for help
INN number INN
412 phenacetin
Synonyms Click here for help
acetophenetidin
Database Links Click here for help
CAS Registry No. 62-44-2
ChEMBL Ligand CHEMBL16073
DrugBank Ligand DB03783
DrugCentral Ligand 2115
GtoPdb PubChem SID 178103974
PubChem CID 4754
RCSB PDB Ligand N4E
Search Google for chemical match using the InChIKey CPJSUEIXXCENMM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CPJSUEIXXCENMM
Search PubMed clinical trials phenacetin
Search PubMed titles phenacetin
Search PubMed titles/abstracts phenacetin
UniChem Compound Search for chemical match using the InChIKey CPJSUEIXXCENMM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CPJSUEIXXCENMM-UHFFFAOYSA-N
Wikipedia Phenacetin