3-Bromo-4-oxo-1-(3'-deoxy-beta-D-ribofuranosyl)pyrazolo[3,4-d]-pyrimidine

ID: ALA4874629

PubChem CID: 164628839

Max Phase: Preclinical

Molecular Formula: C10H11BrN4O4

Molecular Weight: 331.13

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]cnc2c1c(Br)nn2[C@@H]1O[C@H](CO)C[C@H]1O

Standard InChI:  InChI=1S/C10H11BrN4O4/c11-7-6-8(12-3-13-9(6)18)15(14-7)10-5(17)1-4(2-16)19-10/h3-5,10,16-17H,1-2H2,(H,12,13,18)/t4-,5+,10+/m0/s1

Standard InChI Key:  BIDWPRMVBBJVAS-LBACSGLVSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    2.2974  -28.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225  -28.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3781  -27.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078  -27.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460  -27.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609  -27.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1635  -27.6630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0856  -26.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6043  -29.3691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468  -26.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4216  -26.8814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036  -27.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8356  -28.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9189  -28.9669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696  -29.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378  -28.8179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2511  -28.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9151  -27.5161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292  -26.2179    0.0000 Br  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
  2  9  1  6
  7 13  1  0
 12 10  1  0
 10 11  2  0
 11  7  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 12  1  0
 17 18  2  0
 10 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874629

   ---

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: 331.13

Molecular Weight (Monoisotopic): 329.9964

AlogP: -0.48

#Rotatable Bonds: 2

Polar Surface Area: 113.26

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.31

CX Basic pKa: ┄

CX LogP: -0.88

CX LogD: -0.88

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.69

Np Likeness Score: 0.50

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