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

ID: ALA4561102

PubChem CID: 155558655

Max Phase: Preclinical

Molecular Formula: C16H16ClN5O4

Molecular Weight: 377.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccc(Cl)cn1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H16ClN5O4/c17-7-1-2-9(19-3-7)8-4-22(15-11(8)14(18)20-6-21-15)16-13(25)12(24)10(5-23)26-16/h1-4,6,10,12-13,16,23-25H,5H2,(H2,18,20,21)/t10-,12-,13-,16-/m1/s1

Standard InChI Key:  RWDQSSUIMJQEHO-XNIJJKJLSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   14.1192  -28.7338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3475  -29.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3545  -27.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1758  -27.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1081  -29.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6706  -28.5398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7879  -29.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2868  -29.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4482  -28.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0144  -29.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9253  -27.2438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5679  -27.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1387  -26.5092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -26.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6075  -30.4424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3892  -27.1819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8163  -30.4796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2302  -28.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5203  -29.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1540  -29.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1502  -29.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8552  -30.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5629  -29.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5612  -29.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8557  -28.7029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2706  -30.3360    0.0000 Cl  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
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4561102

   ---

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: 377.79

Molecular Weight (Monoisotopic): 377.0891

AlogP: 0.34

#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: 6.23

CX LogP: 0.14

CX LogD: 0.11

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: 0.26

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