General Information of the Compound
Compound ID
CP0394229
Compound Name
(2R,3R,4S,5R)-2-(6-amino-2-(2-(5-hydroxy-1H-indol-3-yl)ethoxy)-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol
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Synonyms
2-(3''''-(5''''-hydroxyindolyl)ethyloxy)adenosine
2-(3''-(5''-hydroxyindolyl)ethyloxy)adenosine
BDBM50208785
CHEMBL222500
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Structure
Formula
C20H22N6O6
Molecular Weight
442.432
Canonical SMILES
Nc1nc(OCCc2c[nH]c3ccc(O)cc23)nc2n(cnc12)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
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InChI
InChI=1S/C20H22N6O6/c21-17-14-18(26(8-23-14)19-16(30)15(29)13(7-27)32-19)25-20(24-17)31-4-3-9-6-22-12-2-1-10(28)5-11(9)12/h1-2,5-6,8,13,15-16,19,22,27-30H,3-4,7H2,(H2,21,24,25)/t13-,15-,16-,19-/m1/s1
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InChIKey
CPKNPTKTLVLFFU-NVQRDWNXSA-N
Physicochemical Property
logP
-0.1716
Rotatable Bonds
6
Heavy Atom Count
32
Polar Areas
184.79
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
11
Complexity
32

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 16202841
SID: 24842555
ChEMBL ID
CHEMBL222500
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00840, Adenosine receptor A1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 310 nM
   TI
   LI
   LO
   TS
Protein ID: PT00862, Adenosine receptor A2a
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 450 nM
   TI
   LI
   LO
   TS
Protein ID: PT01278, Adenosine receptor A2b
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
EC50 = 896 nM
   TI
   LI
   LO
   TS
Protein ID: PT01279, Adenosine receptor A3
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 120 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( 2-(3''-(5''-hydroxyindolyl)ethyloxy)adenosine )
Drug Name 2-(3''-(5''-hydroxyindolyl)ethyloxy)adenosine
Target(s)
Adenosine A2a receptor (ADORA2A)
Inhibitor
Adenosine A1 receptor (ADORA1)
Inhibitor
Adenosine A3 receptor (ADORA3)
Inhibitor