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

ID: ALA5207667

PubChem CID: 168297248

Max Phase: Preclinical

Molecular Formula: C12H15N3O4

Molecular Weight: 265.27

Names and Identifiers

Canonical SMILES:  Nc1cnc2c(ccn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C12H15N3O4/c13-7-3-6-1-2-15(11(6)14-4-7)12-10(18)9(17)8(5-16)19-12/h1-4,8-10,12,16-18H,5,13H2/t8-,9-,10-,12-/m1/s1

Standard InChI Key:  CUICMNYNTGBVDV-DNRKLUKYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -1.4878    0.4048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9727   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2101    0.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -1.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7032   -0.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357   -1.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7032    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357    0.6347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0843   -0.3738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9048   -0.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897    0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.1211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541    0.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337    1.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    1.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357    1.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  1  0
  2  5  1  0
  5  6  1  6
  7  5  1  0
  7  8  1  6
  9  7  1  0
  1  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 17 16  1  0
 11 17  2  0
 18 17  1  0
 19 18  2  0
 19 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5207667

   ---

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: 265.27

Molecular Weight (Monoisotopic): 265.1063

AlogP: -0.77

#Rotatable Bonds: 2

Polar Surface Area: 113.76

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 4.52

CX LogP: -1.17

CX LogD: -1.17

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.57

Np Likeness Score: 0.77

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