Cl-IB-MECA   Click here for help

GtoPdb Ligand ID: 457

Synonyms: 2Cl-IB-MECA
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 134.42
Molecular weight 544.01
XLogP 2.91
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(=O)C1OC(C(C1O)O)n1cnc2c1nc(Cl)nc2NCc1cccc(c1)I
Isomeric SMILES CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2NCc1cccc(c1)I
InChI InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1
InChI Key IPSYPUKKXMNCNQ-PFHKOEEOSA-N
References
1. Brambilla R, Cattabeni F, Ceruti S, Barbieri D, Franceschi C, Kim YC, Jacobson KA, Klotz KN, Lohse MJ, Abbracchio MP. (2000)
Activation of the A3 adenosine receptor affects cell cycle progression and cell growth.
Naunyn Schmiedebergs Arch. Pharmacol., 361 (3): 225-34. [PMID:10731034]
2. Jacobson KA, Gao ZG. (2006)
Adenosine receptors as therapeutic targets.
Nat Rev Drug Discov, 5 (3): 247-64. [PMID:16518376]
3. Jacobson KA, Park KS, Jiang JL, Kim YC, Olah ME, Stiles GL, Ji XD. (1997)
Pharmacological characterization of novel A3 adenosine receptor-selective antagonists.
Neuropharmacology, 36 (9): 1157-65. [PMID:9364471]
4. Kim HO, Ji XD, Siddiqi SM, Olah ME, Stiles GL, Jacobson KA. (1994)
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.
J. Med. Chem., 37 (21): 3614-21. [PMID:7932588]
5. 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]