xanthine amine congener   Click here for help

GtoPdb Ligand ID: 404

Abbreviated name: XAC
PDB Ligand
Compound class: Synthetic organic
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
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 6
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 137.03
Molecular weight 428.22
XLogP 3.37
No. Lipinski's rules broken 0
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)c1ccc(cc1)OCC(=O)NCCN
Isomeric SMILES CCCn1c2nc([nH]c2c(=O)n(c1=O)CCC)c1ccc(cc1)OCC(=O)NCCN
InChI InChI=1S/C21H28N6O4/c1-3-11-26-19-17(20(29)27(12-4-2)21(26)30)24-18(25-19)14-5-7-15(8-6-14)31-13-16(28)23-10-9-22/h5-8H,3-4,9-13,22H2,1-2H3,(H,23,28)(H,24,25)
InChI Key FIQGIOAELHTLHM-UHFFFAOYSA-N
References
1. Alexander SP, Cooper J, Shine J, Hill SJ. (1996)
Characterization of the human brain putative A2B adenosine receptor expressed in Chinese hamster ovary (CHO.A2B4) cells.
Br J Pharmacol, 119 (6): 1286-90. [PMID:8937736]
2. Beukers MW, den Dulk H, van Tilburg EW, Brouwer J, Ijzerman AP. (2000)
Why are A(2B) receptors low-affinity adenosine receptors? Mutation of Asn273 to Tyr increases affinity of human A(2B) receptor for 2-(1-Hexynyl)adenosine.
Mol Pharmacol, 58 (6): 1349-56. [PMID:11093773]
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. Franchetti P, Cappellacci L, Vita P, Petrelli R, Lavecchia A, Kachler S, Klotz KN, Marabese I, Luongo L, Maione S et al.. (2009)
N6-Cycloalkyl- and N6-bicycloalkyl-C5'(C2')-modified adenosine derivatives as high-affinity and selective agonists at the human A1 adenosine receptor with antinociceptive effects in mice.
J Med Chem, 52 (8): 2393-406. [PMID:19317449]
5. Ji X, Kim YC, Ahern DG, Linden J, Jacobson KA. (2001)
[3H]MRS 1754, a selective antagonist radioligand for A(2B) adenosine receptors.
Biochem Pharmacol, 61 (6): 657-63. [PMID:11266650]
6. Ji XD, Jacobson KA. (1999)
Use of the triazolotriazine [3H]ZM 241385 as a radioligand at recombinant human A2B adenosine receptors.
Drug Des Discov, 16 (3): 217-26. [PMID:10624567]
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.
J Biol Chem, 269 (51): 32077-84. [PMID:7798201]
8. 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]
9. Linden J, Thai T, Figler H, Jin X, Robeva AS. (1999)
Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells.
Mol Pharmacol, 56 (4): 705-13. [PMID:10496952]
10. Olah ME, Jacobson KA, Stiles GL. (1994)
Role of the second extracellular loop of adenosine receptors in agonist and antagonist binding. Analysis of chimeric A1/A3 adenosine receptors.
J Biol Chem, 269 (40): 24692-8. [PMID:7929142]
11. Salvatore CA, Jacobson MA, Taylor HE, Linden J, Johnson RG. (1993)
Molecular cloning and characterization of the human A3 adenosine receptor.
Proc Natl Acad Sci USA, 90 (21): 10365-9. [PMID:8234299]
12. Stewart M, Steinig AG, Ma C, Song JP, McKibben B, Castelhano AL, MacLennan SJ. (2004)
[3H]OSIP339391, a selective, novel, and high affinity antagonist radioligand for adenosine A2B receptors.
Biochem Pharmacol, 68 (2): 305-12. [PMID:15194002]
13. Varani K, Merighi S, Gessi S, Klotz KN, Leung E, Baraldi PG, Cacciari B, Romagnoli R, Spalluto G, Borea PA. (2000)
[(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.
Mol Pharmacol, 57 (5): 968-75. [PMID:10779381]