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

ID: ALA4872889

PubChem CID: 164619482

Max Phase: Preclinical

Molecular Formula: C15H22N6O5

Molecular Weight: 366.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(CN1CCOCC1)nn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H22N6O5/c16-13-10-8(5-20-1-3-25-4-2-20)19-21(14(10)18-7-17-13)15-12(24)11(23)9(6-22)26-15/h7,9,11-12,15,22-24H,1-6H2,(H2,16,17,18)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  PPAINDMAUCFONT-SDBHATRESA-N

Molfile:  

 
     RDKit          2D

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    1.9810  -22.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8024  -22.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567  -21.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896  -21.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309  -21.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9495  -21.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8384  -21.5396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751  -20.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4957  -23.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819  -23.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9166  -20.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0953  -20.7617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1722  -21.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5074  -22.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5903  -22.8373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374  -23.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0024  -22.6850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162  -21.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5770  -21.3934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3967  -20.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2094  -20.1866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5384  -20.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3474  -21.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8312  -20.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000  -19.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6850  -19.5258    0.0000 C   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
 11 20  1  0
 20 21  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872889

   ---

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: 366.38

Molecular Weight (Monoisotopic): 366.1652

AlogP: -2.15

#Rotatable Bonds: 4

Polar Surface Area: 152.01

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.42

CX Basic pKa: 5.05

CX LogP: -2.35

CX LogD: -2.35

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.47

Np Likeness Score: -0.07

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