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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View more information in the IUPHAR Pharmacology Education Project: caffeine

caffeine 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 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
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
A2A receptor Primary target of this compound Hs Antagonist Antagonist 4.6 – 5.6 pKi - 1,8,10
⤷ pKi 4.6 – 5.6 [1,8,10]
A2B receptor Mm Antagonist Antagonist 4.9 pKi - 4
⤷ pKi 4.9 (Ki 1.3x10-5 M) [4]
A3 receptor Primary target of this compound Hs Antagonist Antagonist 4.9 pKi - 8
⤷ pKi 4.9 (Ki 1.33x10-5 M) [8]
A2B receptor Primary target of this compound Hs Antagonist Antagonist 4.5 – 5.0 pKi - 2-3,9
⤷ pKi 4.5 – 5.0 (Ki 3.38x10-5 – 1.04x10-5 M) [2-3,9]
A1 receptor Primary target of this compound Hs Antagonist Antagonist 4.3 – 5.0 pKi - 1,6,8
⤷ pKi 4.3 – 5.0 (Ki 4.49x10-5 – 1.07x10-5 M) [1,6,8]
A2B receptor Rn Antagonist Antagonist 4.5 pKi - 4
⤷ pKi 4.5 (Ki 3x10-5 M) [4]
A2A receptor Rn Antagonist Antagonist 4.3 – 4.5 pKi - 5,8,11
⤷ pKi 4.3 – 4.5 (Ki 4.8x10-5 – 3.25x10-5 M) [5,8,11]
A1 receptor Rn Antagonist Antagonist 4.4 – 4.4 pKi - 5,7
⤷ pKi 4.4 – 4.4 (Ki 4.4x10-5 – 4.1x10-5 M) [5,7]
A3 receptor Rn Antagonist Antagonist <4.0 pKi - 3
⤷ pKi <4.0 (Ki >1x10-4 M) [3]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
IP3R1 Hs Antagonist Antagonist - - -
⤷ mM range
RyR1 Hs Activator - - - -
⤷ pharmacological; mM range
RyR2 Hs Activator - - - -
⤷ pharmacological; mM range
RyR3 Hs Activator - - - -
⤷ pharmacological; mM range
Ligand mentioned in the following text fields
Adenosine receptors overview