caffeine   Click here for help

GtoPdb Ligand ID: 407

Synonyms: Peyona®
Approved drug PDB Ligand
caffeine is an approved drug (FDA (no history prior to 1999), EMA (2009))
Compound class: Natural product or derivative
Comment: Caffeine is a central nervous system stimulant that causes increased alertness and agitation.
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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

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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 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 3
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 61.82
Molecular weight 194.08
XLogP 1.55
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 Cn1cnc2c1c(=O)n(C)c(=O)n2C
Isomeric SMILES Cn1cnc2c1c(=O)n(C)c(=O)n2C
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChI Key RYYVLZVUVIJVGH-UHFFFAOYSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (no history prior to 1999), EMA (2009))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
1,3,7-trimethylpurine-2,6-dione
Synonyms Click here for help
Peyona®
Database Links Click here for help
Specialist databases
GPCRdb Ligand caffeine
Other databases
BindingDB Ligand 10849
BitterDB Ligand 46
CAS Registry No. 58-08-2
ChEBI CHEBI:27732
ChEMBL Ligand CHEMBL113
DrugBank Ligand DB00201
DrugCentral Ligand 463
GtoPdb PubChem SID 135652675
PubChem CID 2519
RCSB PDB Ligand CFF
Search Google for chemical match using the InChIKey RYYVLZVUVIJVGH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RYYVLZVUVIJVGH
SynPHARM 1495 (in complex with A2A receptor)
UniChem Compound Search for chemical match using the InChIKey RYYVLZVUVIJVGH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RYYVLZVUVIJVGH-UHFFFAOYSA-N
Wikipedia Caffeine

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

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Tocris
Caffeine (links to external site)
Cat. No. 2793