4-Methylamino-N7-(beta-L-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine

ID: ALA5187821

PubChem CID: 168281497

Max Phase: Preclinical

Molecular Formula: C12H16N4O4

Molecular Weight: 280.28

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H16N4O4/c1-13-10-6-2-3-16(11(6)15-5-14-10)12-9(19)8(18)7(4-17)20-12/h2-3,5,7-9,12,17-19H,4H2,1H3,(H,13,14,15)/t7-,8-,9-,12-/m0/s1

Standard InChI Key:  VEMBQZKPZAZEFQ-PEFMBERDSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -1.7940   -0.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085    0.1932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2231   -0.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940   -1.0444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -1.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648   -1.0444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648   -0.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2482    0.3327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    0.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784   -1.3070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115   -0.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636   -1.1194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3831    0.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2231    1.4568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685    0.7131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078    1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794    0.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  6
 14 12  1  0
 14 15  1  1
 15 16  1  0
 17  9  1  0
 17 14  1  0
  8 18  1  0
 19 18  2  0
 20 19  1  0
  7 20  1  0
 20  1  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5187821

   ---

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: 280.28

Molecular Weight (Monoisotopic): 280.1172

AlogP: -0.92

#Rotatable Bonds: 3

Polar Surface Area: 112.66

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 6.36

CX LogP: -0.98

CX LogD: -1.01

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: 0.83

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