(R)-8-ethyl-2-(4-hydroxybicyclo[2.2.2]octan-1-yl)-4-propyl-7,8-dihydro-1H-imidazo[1,2-g]purin-5(4H)-one

ID: ALA450341

PubChem CID: 135428645

Max Phase: Preclinical

Molecular Formula: C20H29N5O2

Molecular Weight: 371.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCN1C(=O)N2C[C@@H](CC)N=C2c2[nH]c(C34CCC(O)(CC3)CC4)nc21

Standard InChI:  InChI=1S/C20H29N5O2/c1-3-11-24-16-14(15-21-13(4-2)12-25(15)18(24)26)22-17(23-16)19-5-8-20(27,9-6-19)10-7-19/h13,27H,3-12H2,1-2H3,(H,22,23)/t13-,19?,20?/m1/s1

Standard InChI Key:  UOQYIXROQIKTLQ-JYMLRBTQSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   -1.6125   -1.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -0.2651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    1.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498    1.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414   -0.5743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683    0.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9539    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8214   -0.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8223   -3.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482   -4.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -5.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120    1.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4602    0.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082    1.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3211    2.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2810    3.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329    3.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4966    2.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244    1.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2125   -2.9168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865    2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414    2.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2267    3.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  4  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  3  7  1  0
  6  7  1  0
  1  8  1  0
  3  9  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 11 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16 21  1  0
 20 21  1  0
 16 22  1  0
 19 23  1  0
 22 23  1  0
  1 24  2  0
 19 25  1  0
 11 26  1  1
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA450341

   ---

2. Alternative Forms:

   

   ALA450341

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 371.49

Molecular Weight (Monoisotopic): 371.2321

AlogP: 2.94

#Rotatable Bonds: 4

Polar Surface Area: 84.82

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: 5.07

CX LogP: 2.41

CX LogD: 2.41

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: 0.05

References

1. Vu CB, Kiesman WF, Conlon PR, Lin KC, Tam M, Petter RC, Smits G, Lutterodt F, Jin X, Chen L, Zhang J..  (2006)  Tricyclic imidazoline derivatives as potent and selective adenosine A1 receptor antagonists.,  49  (24): [PMID:17125265] [10.1021/jm060539t]

2. Baraldi PG, Preti D, Zaid AN, Saponaro G, Tabrizi MA, Baraldi S, Romagnoli R, Moorman AR, Varani K, Cosconati S, Di Maro S, Marinelli L, Novellino E, Borea PA..  (2011)  New 2-heterocyclyl-imidazo[2,1-i]purin-5-one derivatives as potent and selective human A3 adenosine receptor antagonists.,  54  (14): [PMID:21675777] [10.1021/jm2004738]

Source

Source(1):

• Scientific Literature