4-amino-5-(1-methyl-1H-imidazol-5-yl)-N7-(beta-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine

ID: ALA4448104

PubChem CID: 155519673

Max Phase: Preclinical

Molecular Formula: C15H18N6O4

Molecular Weight: 346.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cncc1-c1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c2ncnc(N)c12

Standard InChI:  InChI=1S/C15H18N6O4/c1-20-6-17-2-8(20)7-3-21(14-10(7)13(16)18-5-19-14)15-12(24)11(23)9(4-22)25-15/h2-3,5-6,9,11-12,15,22-24H,4H2,1H3,(H2,16,18,19)/t9-,11-,12-,15-/m1/s1

Standard InChI Key:  RQRLWQIRZMRGAT-SDBHATRESA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   13.3144  -22.1467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5426  -22.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5497  -21.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3710  -21.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3033  -23.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8658  -21.9527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9831  -22.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4819  -23.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6434  -22.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2096  -22.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1205  -20.6568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7631  -20.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3339  -19.9221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5125  -19.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8027  -23.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5844  -20.5949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0114  -23.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4254  -22.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155  -22.6172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3492  -22.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4379  -23.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2354  -23.5034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6440  -22.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0990  -22.1910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2705  -21.3920    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 20  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4448104

   ---

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: 346.35

Molecular Weight (Monoisotopic): 346.1390

AlogP: -0.97

#Rotatable Bonds: 3

Polar Surface Area: 144.47

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 6.73

CX LogP: -1.61

CX LogD: -1.66

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: 0.78

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