3-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl)propanoic acid

ID: ALA414157

Max Phase: Phase

Molecular Formula: C22H32N4O4

Molecular Weight: 416.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tonapofylline | BG-9928 | BG9928

Canonical SMILES:  CCCn1c(=O)c2[nH]c(C34CCC(CCC(=O)O)(CC3)CC4)nc2n(CCC)c1=O

Standard InChI:  InChI=1S/C22H32N4O4/c1-3-13-25-17-16(18(29)26(14-4-2)20(25)30)23-19(24-17)22-10-7-21(8-11-22,9-12-22)6-5-15(27)28/h3-14H2,1-2H3,(H,23,24)(H,27,28)

Standard InChI Key:  ZWTVVWUOTJRXKM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   -3.1583    0.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1583   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4463   -0.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4463    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -0.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9487   -0.7980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4631   -0.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9487    0.5385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619   -0.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717   -0.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931   -0.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982    0.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7706    0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8345   -0.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497    0.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899    1.2788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845   -0.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4463    1.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4468   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325   -2.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -1.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8722   -0.9552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    0.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5873    0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3029    0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0708    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833   -0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9958   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 30 13  1  0
 13 14  1  0
  2  3  1  0
 30 15  1  0
  3  6  1  0
 15 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  2  0
 17 18  2  0
  8  9  1  0
 17 19  1  0
  9  5  1  0
  4 20  2  0
  5  4  1  0
  3 21  1  0
  8 10  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
  2 24  2  0
  1 25  1  0
  1  2  1  0
 25 26  1  0
  1  4  1  0
 26 27  1  0
 10 14  1  0
 10 28  1  0
 11 12  1  0
 28 29  1  0
 12 30  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA414157

   TONAPOFYLLINE

2. Alternative Forms:

   

   ALA414157

   3-[4-(2,6-dioxo-1,3-dipropyl-7H-purin-8-yl)-1-bicyclo[2.2.2]octanyl]propanoic acid;hydrochloride

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 416.52

Molecular Weight (Monoisotopic): 416.2424

AlogP: 3.16

#Rotatable Bonds: 8

Polar Surface Area: 109.98

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.13

CX Basic pKa: ┄

CX LogP: 3.47

CX LogD: 0.29

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: -0.11

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. Scheiff AB, Yerande SG, El-Tayeb A, Li W, Inamdar GS, Vasu KK, Sudarsanam V, Müller CE..  (2010)  2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists.,  18  (6): [PMID:20188574] [10.1016/j.bmc.2010.01.072]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names