3-Methylamido-4-amino-1-(beta-D-ribofuranosyl)pyrazolo[3,4-d]-pyrimidine

ID: ALA4872365

PubChem CID: 164618685

Max Phase: Preclinical

Molecular Formula: C12H16N6O5

Molecular Weight: 324.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1nn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12

Standard InChI:  InChI=1S/C12H16N6O5/c1-14-11(22)6-5-9(13)15-3-16-10(5)18(17-6)12-8(21)7(20)4(2-19)23-12/h3-4,7-8,12,19-21H,2H2,1H3,(H,14,22)(H2,13,15,16)/t4-,7-,8-,12-/m1/s1

Standard InChI Key:  AUIRANFWWHILHU-BFAGERDPSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   18.2547  -22.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0760  -22.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3304  -21.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6633  -21.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0046  -21.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2231  -21.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1121  -21.3703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0487  -20.5662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7694  -23.0673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5556  -23.0684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1902  -20.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3690  -20.5924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4458  -21.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7810  -21.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8640  -22.6681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6111  -23.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2761  -22.5158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1898  -21.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8506  -21.2242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6704  -19.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4831  -20.0173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3378  -19.1857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9632  -19.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  1
  3  7  1  1
  6  8  1  0
  1  9  1  6
  2 10  1  6
  7 14  1  0
 13 11  1  0
 11 12  2  0
 12  7  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
 11 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872365

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 324.30

Molecular Weight (Monoisotopic): 324.1182

AlogP: -2.62

#Rotatable Bonds: 3

Polar Surface Area: 168.64

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.41

CX Basic pKa: 3.19

CX LogP: -2.69

CX LogD: -2.69

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.41

Np Likeness Score: 0.23

References

1. Bouton J, Ferreira de Almeida Fiuza L, Cardoso Santos C, Mazzarella MA, Soeiro MNC, Maes L, Karalic I, Caljon G, Van Calenbergh S..  (2021)  Revisiting Pyrazolo[3,4-d]pyrimidine Nucleosides as Anti-Trypanosoma cruzi and Antileishmanial Agents.,  64  (7.0): [PMID:33784107] [10.1021/acs.jmedchem.1c00135]

Source

Source(1):

• Scientific Literature