2-Amino-4-amino-N7-(beta-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine

ID: ALA5174803

PubChem CID: 9835419

Max Phase: Preclinical

Molecular Formula: C11H15N5O4

Molecular Weight: 281.27

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2ccn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C11H15N5O4/c12-8-4-1-2-16(9(4)15-11(13)14-8)10-7(19)6(18)5(3-17)20-10/h1-2,5-7,10,17-19H,3H2,(H4,12,13,14,15)/t5-,6-,7-,10-/m1/s1

Standard InChI Key:  KBBXIXQBRHFCHC-DAGMQNCNSA-N

Molfile:  

 
     RDKit          2D

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   -2.8745    0.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4620   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1521    0.4047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676   -0.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1521   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -1.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2996   -1.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2996    0.6347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0843    0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198   -0.3738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -0.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7252    0.2073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897    0.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745    1.6283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    1.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0843    1.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2996    1.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6528   -1.1747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  1
  4  3  1  0
  4  5  1  0
  6  5  1  0
  7  6  1  0
  3  7  1  0
  7  8  1  6
  6  9  1  6
  5 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 11 17  2  0
 17 18  1  0
 18 19  2  0
 19 10  1  0
 13 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5174803

   (2R,3R,4S,5R)-2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 281.27

Molecular Weight (Monoisotopic): 281.1124

AlogP: -1.79

#Rotatable Bonds: 2

Polar Surface Area: 152.67

Molecular Species: BASE

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.46

CX Basic pKa: 8.55

CX LogP: -1.43

CX LogD: -2.55

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.43

Np Likeness Score: 0.88

References

1. Lin C, Jaén Batista DDG, Mazzeti AL, Donola Girão R, de Oliveira GM, Karalic I, Hulpia F, Soeiro MNC, Maes L, Caljon G, Van Calenbergh S..  (2022)  N⁶-modification of 7-Deazapurine nucleoside analogues as Anti-Trypanosoma cruzi and anti-Leishmania agents: Structure-activity relationship exploration and In vivo evaluation.,  231  [PMID:35144125] [10.1016/j.ejmech.2022.114165]

Source

Source(1):

• Scientific Literature