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

ID: ALA4782563

PubChem CID: 9813950

Max Phase: Preclinical

Molecular Formula: C11H14N4O4

Molecular Weight: 266.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncc2ccn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C11H14N4O4/c12-11-13-3-5-1-2-15(9(5)14-11)10-8(18)7(17)6(4-16)19-10/h1-3,6-8,10,16-18H,4H2,(H2,12,13,14)/t6-,7-,8-,10-/m1/s1

Standard InChI Key:  LLNFXZMJZLXTOG-FDDDBJFASA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   17.2435  -16.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0648  -16.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3192  -16.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6563  -15.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9934  -16.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1032  -15.7581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1822  -14.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3609  -14.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4337  -15.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7676  -16.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8518  -17.0570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6013  -17.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2676  -16.9067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1801  -16.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2119  -15.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0417  -14.9573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7623  -17.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5485  -17.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6868  -18.2029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6 10  1  0
  9  7  1  0
  7  8  2  0
  8  6  1  0
  3  6  1  1
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  5 15  1  1
 15 16  1  0
  1 17  1  6
  2 18  1  6
 12 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4782563

   (2R,3R,4S,5R)-2-(2-aminopyrrolo[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: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 266.26

Molecular Weight (Monoisotopic): 266.1015

AlogP: -1.38

#Rotatable Bonds: 2

Polar Surface Area: 126.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 6.68

CX LogP: -1.19

CX LogD: -1.27

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.53

Np Likeness Score: 0.91

References

1. Hulpia F,Bouton J,Campagnaro GD,Alfayez IA,Mabille D,Maes L,de Koning HP,Caljon G,Van Calenbergh S.  (2020)  C6-O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents.,  188  [PMID:31931339] [10.1016/j.ejmech.2019.112018]

2. 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