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

ID: ALA4875805

PubChem CID: 164626527

Max Phase: Preclinical

Molecular Formula: C16H16ClN5O3

Molecular Weight: 361.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccc(Cl)cc1)nn2[C@@H]1O[C@H](CO)C[C@H]1O

Standard InChI:  InChI=1S/C16H16ClN5O3/c17-9-3-1-8(2-4-9)13-12-14(18)19-7-20-15(12)22(21-13)16-11(24)5-10(6-23)25-16/h1-4,7,10-11,16,23-24H,5-6H2,(H2,18,19,20)/t10-,11+,16+/m0/s1

Standard InChI Key:  PBWQEAJTJFGQKI-LYOVBCGYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    2.1997  -15.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256  -15.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815  -14.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6106  -13.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9482  -14.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623  -14.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676  -14.1111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9869  -13.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079  -15.8188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517  -13.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3259  -13.3288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4088  -14.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7402  -14.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237  -15.4162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750  -15.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2438  -15.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570  -14.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8215  -13.9641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6413  -12.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4636  -12.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9514  -12.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6141  -11.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7882  -11.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081  -11.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0967  -10.6736    0.0000 Cl  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  2  0
 17 12  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 10 19  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875805

   ---

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: 361.79

Molecular Weight (Monoisotopic): 361.0942

AlogP: 1.37

#Rotatable Bonds: 3

Polar Surface Area: 119.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.48

CX Basic pKa: 3.84

CX LogP: 1.17

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.64

Np Likeness Score: 0.09

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