adenosine   Click here for help

GtoPdb Ligand ID: 2844

Synonyms: Adenocard® | Adenoscan®
Approved drug PDB Ligand
adenosine is an approved drug (FDA (1989))
Compound class: Metabolite
Comment: Endogenous nucleoside, a component of nucleic acids and an important neurotransmitter.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: adenosine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 139.54
Molecular weight 267.1
XLogP -1.42
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1ncnc2N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
InChI InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
1. Baldwin SA, Yao SY, Hyde RJ, Ng AM, Foppolo S, Barnes K, Ritzel MW, Cass CE, Young JD. (2005)
Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.
J Biol Chem, 280 (16): 15880-7. [PMID:15701636]
2. Fredholm BB. (1995)
Astra Award Lecture. Adenosine, adenosine receptors and the actions of caffeine.
Pharmacol Toxicol, 76 (2): 93-101. [PMID:7746802]
3. Fredholm BB, Chen JF, Masino SA, Vaugeois JM. (2005)
Actions of adenosine at its receptors in the CNS: insights from knockouts and drugs.
Annu Rev Pharmacol Toxicol, 45: 385-412. [PMID:15822182]
4. Tai AW, Bojjireddy N, Balla T. (2011)
A homogeneous and nonisotopic assay for phosphatidylinositol 4-kinases.
Anal Biochem, 417 (1): 97-102. [PMID:21704602]
5. Yan L, Burbiel JC, Maass A, Müller CE. (2003)
Adenosine receptor agonists: from basic medicinal chemistry to clinical development.
Expert Opin Emerg Drugs, 8 (2): 537-76. [PMID:14662005]
6. Yao SY, Ng AM, Cass CE, Baldwin SA, Young JD. (2011)
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).
J Biol Chem, 286 (37): 32552-62. [PMID:21795683]
7. Zhou M, Duan H, Engel K, Xia L, Wang J. (2010)
Adenosine transport by plasma membrane monoamine transporter: reinvestigation and comparison with organic cations.
Drug Metab Dispos, 38 (10): 1798-805. [PMID:20592246]