cyclopentyladenosine   Click here for help

GtoPdb Ligand ID: 380

Abbreviated name: CPA
Synonyms: N(6)-cyclopentyladenosine | N6-cyclopentyladenosine
PDB Ligand
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 335.16
XLogP 0.3
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1ncnc2NC1CCCC1
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NC1CCCC1
InChI InChI=1S/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1
InChI Key SQMWSBKSHWARHU-SDBHATRESA-N
References
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Thermodynamics of full agonist, partial agonist, and antagonist binding to wild-type and mutant adenosine A1 receptors.
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2. de Ligt RA, Rivkees SA, Lorenzen A, Leurs R, IJzerman AP. (2005)
A "locked-on," constitutively active mutant of the adenosine A1 receptor.
Eur. J. Pharmacol., 510 (1-2): 1-8. [PMID:15740718]
3. Gao ZG, Mamedova LK, Chen P, Jacobson KA. (2004)
2-Substituted adenosine derivatives: affinity and efficacy at four subtypes of human adenosine receptors.
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Allosteric modulation, thermodynamics and binding to wild-type and mutant (T277A) adenosine A1 receptors of LUF5831, a novel nonadenosine-like agonist.
Br. J. Pharmacol., 147 (5): 533-41. [PMID:16444290]
5. Jacobson KA, Gao ZG. (2006)
Adenosine receptors as therapeutic targets.
Nat Rev Drug Discov, 5 (3): 247-64. [PMID:16518376]
6. 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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7. 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]
8. Liang BT Urso R Sambraski E, Jacobson KA. (2010)
Adenosine A3 receptors in muscle protection.  In  Adenosine Receptors from Cell Biology to Pharmacology
Edited by Borea P (Springer) 257-280. [ISBN:9789048131440]
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. 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]
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. U.S.A., 90 (21): 10365-9. [PMID:8234299]