8-(4-hydroxybicyclo[2.2.2]octan-1-yl)-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione

ID: ALA218458

PubChem CID: 9950776

Max Phase: Preclinical

Molecular Formula: C19H28N4O3

Molecular Weight: 360.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCn1c(=O)c2nc(C34CCC(O)(CC3)CC4)[nH]c2n(CCC)c1=O

Standard InChI:  InChI=1S/C19H28N4O3/c1-3-11-22-14-13(15(24)23(12-4-2)17(22)25)20-16(21-14)18-5-8-19(26,9-6-18)10-7-18/h26H,3-12H2,1-2H3,(H,20,21)

Standard InChI Key:  JMEHHVKPUQMNOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.3708   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0829   -0.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7948   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5804   -0.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0660   -0.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5805    0.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3748    0.2981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0829    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0824   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3677   -2.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6535   -1.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8910   -0.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3009   -0.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1223   -0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5387   -0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1274    0.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2998    0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7375    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7375   -0.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6560   -0.9410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0828    1.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6600    0.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9458    0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2311    0.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3625   -0.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  9  1  0
  6 13  1  0
 13 14  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  3  1  0
  8  9  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  3  4  2  0
 13 19  1  0
 19 20  1  0
 20 16  1  0
  8  1  1  0
  1 21  2  0
  2 10  1  0
  9 22  2  0
  1  2  1  0
  8 23  1  0
 10 11  1  0
 23 24  1  0
  2  4  1  0
 24 25  1  0
 11 12  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA218458

   8-(4-hydroxybicyclo[2.2.2]octan-1-yl)-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione

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: 360.46

Molecular Weight (Monoisotopic): 360.2161

AlogP: 2.04

#Rotatable Bonds: 5

Polar Surface Area: 92.91

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.42

CX Basic pKa: 2.47

CX LogP: 2.25

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -0.17

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]

Source

Source(1):

• Scientific Literature