3-Aminomethyl-4-amino-1-beta-D-ribofuranosylpyrazolo[3,4-d]-pyrimidine

ID: ALA4879324

PubChem CID: 164627806

Max Phase: Preclinical

Molecular Formula: C11H16N6O4

Molecular Weight: 296.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCc1nn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12

Standard InChI:  InChI=1S/C11H16N6O4/c12-1-4-6-9(13)14-3-15-10(6)17(16-4)11-8(20)7(19)5(2-18)21-11/h3,5,7-8,11,18-20H,1-2,12H2,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1

Standard InChI Key:  YOIRBWCZXHEXDU-IOSLPCCCSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   35.6056  -15.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4269  -15.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6813  -14.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0142  -14.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3554  -14.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5740  -14.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4629  -14.5398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3996  -13.7357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1202  -16.2367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9064  -16.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5411  -13.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7198  -13.7619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7967  -14.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1319  -15.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2148  -15.8376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9620  -16.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6270  -15.6852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5407  -14.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2015  -14.3936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0212  -13.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8340  -13.1868    0.0000 N   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
M  END

Alternative Forms

1. Parent:

   

   ALA4879324

   ---

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: 296.29

Molecular Weight (Monoisotopic): 296.1233

AlogP: -2.52

#Rotatable Bonds: 3

Polar Surface Area: 165.56

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.42

CX Basic pKa: 8.41

CX LogP: -2.95

CX LogD: -4.00

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.41

Np Likeness Score: 0.66

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