3-(5-Chlorothiophen-2-yl)-4-amino-1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidine

ID: ALA4875757

PubChem CID: 164629096

Max Phase: Preclinical

Molecular Formula: C14H14ClN5O4S

Molecular Weight: 383.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccc(Cl)s1)nn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H14ClN5O4S/c15-7-2-1-6(25-7)9-8-12(16)17-4-18-13(8)20(19-9)14-11(23)10(22)5(3-21)24-14/h1-2,4-5,10-11,14,21-23H,3H2,(H2,16,17,18)/t5-,10-,11-,14-/m1/s1

Standard InChI Key:  KSBHOFYLZCXOFM-KEDXZAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   18.3473  -14.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1737  -14.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4297  -13.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7585  -13.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0956  -13.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3093  -13.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2162  -13.3676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1339  -12.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8589  -15.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6562  -15.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3011  -12.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4747  -12.5849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5583  -13.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8893  -13.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9728  -14.6735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7246  -15.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3937  -14.5201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3069  -13.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9718  -13.2205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7814  -11.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6037  -11.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8576  -11.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1922  -10.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5272  -11.1366    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.1919   -9.8308    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 20  1  0
 11 20  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875757

   ---

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: 383.82

Molecular Weight (Monoisotopic): 383.0455

AlogP: 0.40

#Rotatable Bonds: 3

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 3.75

CX LogP: 0.43

CX LogD: 0.43

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -0.06

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