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
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
References
1. Abo-Salem OM, Hayallah AM, Bilkei-Gorzo A, Filipek B, Zimmer A, Müller CE. (2004)
Antinociceptive effects of novel A2B adenosine receptor antagonists.
J Pharmacol Exp Ther, 308 (1): 358-66. [PMID:14563788]
2. Bertarelli DC, Diekmann M, Hayallah AM, Rüsing D, Iqbal J, Preiss B, Verspohl EJ, Müller CE. (2006)
Characterization of human and rodent native and recombinant adenosine A(2B) receptors by radioligand binding studies.
Purinergic Signal, 2 (3): 559-71. [PMID:18404493]
3. Borrmann T, Hinz S, Bertarelli DC, Li W, Florin NC, Scheiff AB, Müller CE. (2009)
1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines: development and characterization of adenosine A2B receptor antagonists and a new radioligand with subnanomolar affinity and subtype specificity.
J Med Chem, 52 (13): 3994-4006. [PMID:19569717]
4. Brackett LE, Daly JW. (1994)
Functional characterization of the A2b adenosine receptor in NIH 3T3 fibroblasts.
Biochem Pharmacol, 47 (5): 801-14. [PMID:8135856]
5. Daly JW, Hide I, Müller CE, Shamim M. (1991)
Caffeine analogs: structure-activity relationships at adenosine receptors.
Pharmacology, 42 (6): 309-21. [PMID:1658821]
6. Deckert J, Berger W, Kleopa K, Heckers S, Ransmayr G, Heinsen H, Beckmann H, Riederer P. (1993)
Adenosine A1 receptors in human hippocampus: inhibition of [3H]8-cyclopentyl-1,3-dipropylxanthine binding by antagonist drugs.
Neurosci Lett, 150 (2): 191-4. [PMID:8469419]
7. Grahner B, Winiwarter S, Lanzner W, Müller CE. (1994)
Synthesis and structure-activity relationships of deazaxanthines: analogs of potent A1- and A2-adenosine receptor antagonists.
J Med Chem, 37 (10): 1526-34. [PMID:8182711]
8. Jacobson KA IJzerman AP, Linden J. (1999)
1,3-Dialkylxanthine derivatives having high potency as antagonists at human A2B adenosine receptors.
Drug Dev Res, (47): 45-53.
9. Kim SA, Marshall MA, Melman N, Kim HS, Müller CE, Linden J, Jacobson KA. (2002)
Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions.
J Med Chem, 45 (11): 2131-8. [PMID:12014951]
10. Kull B, Arslan G, Nilsson C, Owman C, Lorenzen A, Schwabe U, Fredholm BB. (1999)
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.
Biochem Pharmacol, 57 (1): 65-75. [PMID:9920286]
11. Müller CE, Maurinsh J, Sauer R. (2000)
Binding of [3H]MSX-2 (3-(3-hydroxypropyl)-7-methyl-8-(m-methoxystyryl)-1-propargylxanthine) to rat striatal membranes--a new, selective antagonist radioligand for A(2A) adenosine receptors.
Eur J Pharm Sci, 10 (4): 259-65. [PMID:10838015]