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

ID: ALA4461564

PubChem CID: 155528542

Max Phase: Preclinical

Molecular Formula: C17H19N5O5

Molecular Weight: 373.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccnc(-c2cn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c3ncnc(N)c23)c1

Standard InChI:  InChI=1S/C17H19N5O5/c1-26-8-2-3-19-10(4-8)9-5-22(16-12(9)15(18)20-7-21-16)17-14(25)13(24)11(6-23)27-17/h2-5,7,11,13-14,17,23-25H,6H2,1H3,(H2,18,20,21)/t11-,13-,14-,17-/m1/s1

Standard InChI Key:  DMPYLTWKBKYNAC-LSCFUAHRSA-N

Molfile:  

 
     RDKit          2D

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   42.1638  -22.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.3920  -22.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3990  -21.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2203  -21.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1526  -23.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7151  -22.0477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.8324  -22.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3313  -23.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4927  -22.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0589  -22.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9698  -20.7517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.6124  -20.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1832  -20.0171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.3619  -20.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6520  -23.9503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.4337  -20.6898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8608  -23.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2747  -22.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5648  -22.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.1985  -22.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1948  -23.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8997  -23.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6074  -23.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6058  -22.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9003  -22.2108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.8983  -24.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.1899  -25.0669    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
 22 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4461564

   ---

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: 373.37

Molecular Weight (Monoisotopic): 373.1386

AlogP: -0.30

#Rotatable Bonds: 4

Polar Surface Area: 148.77

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: 7.22

CX LogP: -0.62

CX LogD: -0.65

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: 0.70

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