4-amino-5-(pyridin-4-yl)-N7-b-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine

ID: ALA4586792

PubChem CID: 155567547

Max Phase: Preclinical

Molecular Formula: C16H17N5O4

Molecular Weight: 343.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccncc1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H17N5O4/c17-14-11-9(8-1-3-18-4-2-8)5-21(15(11)20-7-19-14)16-13(24)12(23)10(6-22)25-16/h1-5,7,10,12-13,16,22-24H,6H2,(H2,17,19,20)/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  PBBGXWCXJKHWIZ-XNIJJKJLSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   22.4067  -16.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6349  -17.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6420  -16.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4633  -16.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3956  -17.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9581  -16.6286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0753  -17.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5742  -17.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7357  -16.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3018  -17.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2127  -15.3327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8554  -15.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4261  -14.5980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6048  -14.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8949  -18.5313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6767  -15.2707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1037  -18.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5177  -16.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8078  -17.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4414  -17.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4377  -18.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1426  -18.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8504  -18.0163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8487  -17.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1432  -16.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  2  0
  5  2  1  0
  6  2  1  0
  7  1  1  0
  8  5  1  0
  9  7  2  0
 10  6  1  0
 11  3  1  0
 12  4  1  0
 13 14  1  0
 14 11  2  0
  5 15  1  6
 16 12  1  0
  8 17  1  6
 10 18  1  1
  9  4  1  0
 10  8  1  0
 12 13  2  0
 18 19  1  0
  9 20  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
M  END

Alternative Forms

1. Parent:

   

   ALA4586792

   ---

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: 343.34

Molecular Weight (Monoisotopic): 343.1281

AlogP: -0.31

#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: 12.46

CX Basic pKa: 6.37

CX LogP: -0.85

CX LogD: -0.89

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: 0.65

References

1. Hulpia F, Campagnaro GD, Scortichini M, Van Hecke K, Maes L, de Koning HP, Caljon G, Van Calenbergh S..  (2019)  Revisiting tubercidin against kinetoplastid parasites: Aromatic substitutions at position 7 improve activity and reduce toxicity.,  164  [PMID:30677668] [10.1016/j.ejmech.2018.12.050]

Source

Source(1):

• Scientific Literature