GtoPdb Ligand ID: 372

Synonyms: 2Cl-Ado | CADO
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 139.54
Molecular weight 301.06
XLogP -0.71
No. Lipinski's rules broken 0
Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1nc(Cl)nc2N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2N
InChI InChI=1S/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
1. 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]
2. Bruns RF. (1980)
Adenosine receptor activation in human fibroblasts: nucleoside agonists and antagonists.
Can. J. Physiol. Pharmacol., 58 (6): 673-91. [PMID:6253037]
3. Daly JW, Padgett WL, Secunda SI, Thompson RD, Olsson RA. (1993)
Structure-activity relationships for 2-substituted adenosines at A1 and A2 adenosine receptors.
Pharmacology, 46 (2): 91-100. [PMID:8441759]
4. 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]
5. Kim J, Wess J, van Rhee AM, Schöneberg T, Jacobson KA. (1995)
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.
J. Biol. Chem., 270 (23): 13987-97. [PMID:7775460]
6. 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]
7. 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]
8. Rivkees SA, Barbhaiya H, IJzerman AP. (1999)
Identification of the adenine binding site of the human A1 adenosine receptor.
J. Biol. Chem., 274 (6): 3617-21. [PMID:9920910]
9. 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]