4-Methylamino-N7-(5'-deoxy-beta-D-ribofuranosyl)-pyrrol[2,3-d]pyrimidine

ID: ALA5178932

PubChem CID: 168271767

Max Phase: Preclinical

Molecular Formula: C12H16N4O3

Molecular Weight: 264.29

Names and Identifiers

Canonical SMILES:  CNc1ncnc2c1ccn2[C@@H]1O[C@H](C)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H16N4O3/c1-6-8(17)9(18)12(19-6)16-4-3-7-10(13-2)14-5-15-11(7)16/h3-6,8-9,12,17-18H,1-2H3,(H,13,14,15)/t6-,8-,9-,12-/m1/s1

Standard InChI Key:  UEGLYEJMOGRKAU-WOUKDFQISA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -1.7688    0.4048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -0.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0237   -1.7147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9842   -0.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167   -1.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9842    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.6348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679    0.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035   -0.3738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240   -0.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089    0.2074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    0.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    1.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788    1.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9528    1.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679    1.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    1.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  6
  6  4  1  0
  6  7  1  6
  8  6  1  0
  1  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 17 14  1  0
 10 17  2  0
 18 17  1  0
 19 18  2  0
 19  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5178932

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 264.29

Molecular Weight (Monoisotopic): 264.1222

AlogP: 0.11

#Rotatable Bonds: 2

Polar Surface Area: 92.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.48

CX Basic pKa: 6.36

CX LogP: 0.07

CX LogD: 0.03

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.71

Np Likeness Score: 0.71

References

1. 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