rolofylline   Click here for help

GtoPdb Ligand ID: 5604

Synonyms: KW-3902 | NAX
Compound class: Synthetic organic
Comment: There is some ambiguity in the literature and on online resources as to the chirality of rolofylline. The structure shown here does not specify stereochemistry and matches the representations shown on Pubchem, Drugbank and Chemspider. Rolofylline is represented on ChEMBL by the entry CHEMBL2103819.
Click here for help

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.

✖

View interactive charts of activity data across species

rolofylline is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 72.68
Molecular weight 356.22
XLogP 5.73
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES CCCn1c2nc([nH]c2c(=O)n(c1=O)CCC)C12CC3CC2CC(C1)C3
Isomeric SMILES CCCn1c2nc([nH]c2c(=O)n(c1=O)CCC)C12CC3CC2CC(C1)C3
InChI InChI=1S/C20H28N4O2/c1-3-5-23-16-15(17(25)24(6-4-2)19(23)26)21-18(22-16)20-10-12-7-13(11-20)9-14(20)8-12/h12-14H,3-11H2,1-2H3,(H,21,22)
InChI Key PJBFVWGQFLYWCB-UHFFFAOYSA-N
References
1. Kiesman WF, Zhao J, Conlon PR, Dowling JE, Petter RC, Lutterodt F, Jin X, Smits G, Fure M, Jayaraj A et al.. (2006)
Potent and orally bioavailable 8-bicyclo[2.2.2]octylxanthines as adenosine A1 receptor antagonists.
J Med Chem, 49 (24): 7119-31. [PMID:17125264]
2. Kiesman WF, Zhao J, Conlon PR, Petter RC, Jin X, Smits G, Lutterodt F, Sullivan GW, Linden J. (2006)
Norbornyllactone-substituted xanthines as adenosine A(1) receptor antagonists.
Bioorg Med Chem, 14 (11): 3654-61. [PMID:16458010]
3. Pfeiffer M, Kirscht S, Stumm R, Koch T, Wu D, Laugsch M, Schröder H, Höllt V, Schulz S. (2003)
Heterodimerization of substance P and mu-opioid receptors regulates receptor trafficking and resensitization.
J Biol Chem, 278 (51): 51630-7. [PMID:14532289]
4. Pfister JR, Belardinelli L, Lee G, Lum RT, Milner P, Stanley WC, Linden J, Baker SP, Schreiner G. (1997)
Synthesis and biological evaluation of the enantiomers of the potent and selective A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbonyl)]-xanthine.
J Med Chem, 40 (12): 1773-8. [PMID:9191953]