3-(3,5-Difluoro-4-chlorophenyl)-4-amino-1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidine

ID: ALA4873603

PubChem CID: 164620744

Max Phase: Preclinical

Molecular Formula: C16H14ClF2N5O4

Molecular Weight: 413.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1cc(F)c(Cl)c(F)c1)nn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H14ClF2N5O4/c17-10-6(18)1-5(2-7(10)19)11-9-14(20)21-4-22-15(9)24(23-11)16-13(27)12(26)8(3-25)28-16/h1-2,4,8,12-13,16,25-27H,3H2,(H2,20,21,22)/t8-,12-,13-,16-/m1/s1

Standard InChI Key:  CWZXGWDPIONLOK-KWDXPJCYSA-N

Molfile:  

 
     RDKit          2D

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   25.6783  -27.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5043  -27.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7602  -26.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0892  -26.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4267  -26.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6407  -26.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5464  -26.2756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4653  -25.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1902  -27.9823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9867  -27.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6307  -25.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8048  -25.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8878  -26.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2192  -26.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3026  -27.5809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0541  -27.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7229  -27.4276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6362  -26.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3007  -26.1286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1203  -24.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9428  -24.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4306  -24.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0933  -23.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2674  -23.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7871  -24.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5760  -22.8376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   31.2480  -24.3382    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.9341  -22.6620    0.0000 F   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
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 11 20  1  0
 23 26  1  0
 22 27  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873603

   ---

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: 413.77

Molecular Weight (Monoisotopic): 413.0702

AlogP: 0.62

#Rotatable Bonds: 3

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 3.83

CX LogP: 0.77

CX LogD: 0.77

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 0.03

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