3-(3,4-Dichlorophenyl)-4-amino-1-beta-D-ribofuranosylpyrazolo-[3,4-d]pyrimidine

ID: ALA4875349

PubChem CID: 164625931

Max Phase: Preclinical

Molecular Formula: C16H15Cl2N5O4

Molecular Weight: 412.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccc(Cl)c(Cl)c1)nn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H15Cl2N5O4/c17-7-2-1-6(3-8(7)18)11-10-14(19)20-5-21-15(10)23(22-11)16-13(26)12(25)9(4-24)27-16/h1-3,5,9,12-13,16,24-26H,4H2,(H2,19,20,21)/t9-,12-,13-,16-/m1/s1

Standard InChI Key:  ZBKFXFLYXINJMO-RVXWVPLUSA-N

Molfile:  

 
     RDKit          2D

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    1.8718  -19.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6979  -19.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9536  -18.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828  -18.1631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203  -18.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345  -18.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398  -18.3950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6591  -17.5864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838  -20.1016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801  -20.1028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8241  -17.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981  -17.6127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0811  -18.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4126  -18.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4959  -19.7002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2473  -20.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161  -19.5470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293  -18.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939  -18.2480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3135  -16.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1359  -17.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6238  -16.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864  -15.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606  -15.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9805  -16.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273  -14.7818    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7691  -14.9574    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
  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
 24 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875349

   ---

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: 412.23

Molecular Weight (Monoisotopic): 411.0501

AlogP: 0.99

#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: 1.09

CX LogD: 1.09

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: -0.04

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