N(6)-cyclohexyladenosine   Click here for help

GtoPdb Ligand ID: 423

Abbreviated name: CHA
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 125.55
Molecular weight 349.18
XLogP 0.87
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1ncnc2NC1CCCCC1
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NC1CCCCC1
InChI InChI=1S/C16H23N5O4/c22-6-10-12(23)13(24)16(25-10)21-8-19-11-14(17-7-18-15(11)21)20-9-4-2-1-3-5-9/h7-10,12-13,16,22-24H,1-6H2,(H,17,18,20)/t10-,12-,13-,16-/m1/s1
InChI Key SZBULDQSDUXAPJ-XNIJJKJLSA-N
References
1. Bruns RF. (1980)
Adenosine receptor activation in human fibroblasts: nucleoside agonists and antagonists.
Can. J. Physiol. Pharmacol., 58 (6): 673-91. [PMID:6253037]
2. 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]
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. 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]
5. Sajjadi FG, Takabayashi K, Foster AC, Domingo RC, Firestein GS. (1996)
Inhibition of TNF-alpha expression by adenosine: role of A3 adenosine receptors.
J. Immunol., 156 (9): 3435-42. [PMID:8617970]
6. 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]