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piracetam   Click here for help

GtoPdb Ligand ID: 4288

Synonyms: Nootropil®
Approved drug PDB Ligand
piracetam is an approved drug (UK (1992))
Compound class: Synthetic organic
Comment: Piracetam is a cyclic derivative of GABA (gamma-aminobutyric acid).

piracetam is commercially available from our sponsors

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 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 63.4
Molecular weight 142.07
XLogP -1.52
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 NC(=O)CN1CCCC1=O
Isomeric SMILES NC(=O)CN1CCCC1=O
InChI InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)
InChI Key GMZVRMREEHBGGF-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 MHRA (1992)
IUPAC Name Click here for help
2-(2-oxopyrrolidin-1-yl)acetamide
International Nonproprietary Names Click here for help
INN number INN
2687 piracetam
Synonyms Click here for help
Nootropil®
Database Links Click here for help
CAS Registry No. 7491-74-9 (source: Scifinder)
ChEMBL Ligand CHEMBL36715
DrugCentral Ligand 2197
GtoPdb PubChem SID 178101105
PubChem CID 4843
RCSB PDB Ligand PZI
Search Google for chemical match using the InChIKey GMZVRMREEHBGGF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GMZVRMREEHBGGF
Search PubMed clinical trials piracetam
Search PubMed titles piracetam
Search PubMed titles/abstracts piracetam
UniChem Compound Search for chemical match using the InChIKey GMZVRMREEHBGGF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GMZVRMREEHBGGF-UHFFFAOYSA-N
Wikipedia Piracetam

Product suppliers

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MedChemExpress
Piracetam (links to external site)
Cat. No. HY-B0585
Piracetam (Standard) (links to external site)
Cat. No. HY-B0585R