theophylline   Click here for help

GtoPdb Ligand ID: 413

Synonyms: Nuelin® | Slo-Bid® | Theolair®
Approved drug PDB Ligand Immunopharmacology Ligand
theophylline is an approved drug (FDA (1976))
Compound class: Natural product or derivative
Comment: Theophylline the parent compound and component of the approved drug aminophylline. Aminophylline is a drug combination that contains theophylline and ethylenediamine (EDTA) in 2:1 ratio.
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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 1
Rotatable bonds 0
Topological polar surface area 72.68
Molecular weight 180.06
XLogP 1.68
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 Cn1c(=O)n(C)c2c(c1=O)[nH]cn2
Isomeric SMILES Cn1c(=O)n(C)c2c(c1=O)[nH]cn2
InChI InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChI Key ZFXYFBGIUFBOJW-UHFFFAOYSA-N
References
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Characterization of the A2B adenosine receptor from mouse, rabbit, and dog.
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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.
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3. Dionisotti S, Ongini E, Zocchi C, Kull B, Arslan G, Fredholm BB. (1997)
Characterization of human A2A adenosine receptors with the antagonist radioligand [3H]-SCH 58261.
Br J Pharmacol, 121 (3): 353-60. [PMID:9179373]
4. Feoktistov I, Garland EM, Goldstein AE, Zeng D, Belardinelli L, Wells JN, Biaggioni I. (2001)
Inhibition of human mast cell activation with the novel selective adenosine A(2B) receptor antagonist 3-isobutyl-8-pyrrolidinoxanthine (IPDX)(2).
Biochem Pharmacol, 62 (9): 1163-73. [PMID:11705449]
5. 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.
6. Jacobson KA, Fischer B, Ji XD. (1995)
"Cleavable trifunctional" approach to receptor affinity labeling: chemical regeneration of binding to A1-adenosine receptors.
Bioconjug Chem, 6 (3): 255-63. [PMID:7632796]
7. Jockers R, Linder ME, Hohenegger M, Nanoff C, Bertin B, Strosberg AD, Marullo S, Freissmuth M. (1994)
Species difference in the G protein selectivity of the human and bovine A1-adenosine receptor.
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8. 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]
9. Klotz KN, Hessling J, Hegler J, Owman C, Kull B, Fredholm BB, Lohse MJ. (1998)
Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.
Naunyn Schmiedebergs Arch Pharmacol, 357 (1): 1-9. [PMID:9459566]
10. Müller CE, Shi D, Manning M, Daly JW. (1993)
Synthesis of paraxanthine analogs (1,7-disubstituted xanthines) and other xanthines unsubstituted at the 3-position: structure-activity relationships at adenosine receptors.
J Med Chem, 36 (22): 3341-9. [PMID:8230124]
11. van Galen PJ, van Bergen AH, Gallo-Rodriguez C, Melman N, Olah ME, IJzerman AP, Stiles GL, Jacobson KA. (1994)
A binding site model and structure-activity relationships for the rat A3 adenosine receptor.
Mol Pharmacol, 45 (6): 1101-11. [PMID:8022403]
12. Varani K, Gessi S, Merighi S, Vincenzi F, Cattabriga E, Benini A, Klotz KN, Baraldi PG, Tabrizi MA, Lennan SM et al.. (2005)
Pharmacological characterization of novel adenosine ligands in recombinant and native human A2B receptors.
Biochem Pharmacol, 70 (11): 1601-12. [PMID:16219300]