(2R,3R,5S)-5-(hydroxymethyl)-2-(4-(methylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3-ol

ID: ALA5209135

PubChem CID: 168295778

Max Phase: Preclinical

Molecular Formula: C12H16N4O3

Molecular Weight: 264.29

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H16N4O3/c1-13-10-8-2-3-16(11(8)15-6-14-10)12-9(18)4-7(5-17)19-12/h2-3,6-7,9,12,17-18H,4-5H2,1H3,(H,13,14,15)/t7-,9+,12+/m0/s1

Standard InChI Key:  KGCYTYNWIZWRJL-LPBBDHJYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -1.5628    0.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0478   -0.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -0.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856    0.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5628   -1.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -0.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.3574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    0.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098   -0.6512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154   -0.0699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799    0.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4648    1.3513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2856    1.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592    0.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    1.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.1826    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
  6  5  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:

   

   ALA5209135

   ---

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: 3

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: 13.53

CX Basic pKa: 6.36

CX LogP: -0.29

CX LogD: -0.32

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.73

Np Likeness Score: 0.86

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