2-amino-4-oxo-N7-(3'-deoxy-3'-fluoro-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

ID: ALA4872128

PubChem CID: 136176848

Max Phase: Preclinical

Molecular Formula: C11H13FN4O4

Molecular Weight: 284.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc2c(ccn2[C@@H]2O[C@H](CO)[C@@H](F)[C@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C11H13FN4O4/c12-6-5(3-17)20-10(7(6)18)16-2-1-4-8(16)14-11(13)15-9(4)19/h1-2,5-7,10,17-18H,3H2,(H3,13,14,15,19)/t5-,6-,7-,10-/m1/s1

Standard InChI Key:  WVHSFPYVRMPQBK-DAGMQNCNSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   40.5459  -18.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3631  -18.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6174  -17.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9545  -17.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.2957  -17.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0647  -19.1423    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.8426  -19.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5184  -17.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3950  -17.4536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3481  -16.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.4654  -16.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6482  -16.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7168  -17.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0510  -17.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1307  -18.7435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.8753  -19.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5412  -18.6064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.4625  -17.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9542  -19.8968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.1261  -17.3125    0.0000 O   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
  1  6  1  6
  2  7  1  6
  5  8  1  1
  3  9  1  1
  8 10  1  0
  9 14  1  0
 13 11  1  0
 11 12  2  0
 12  9  1  0
 13 14  2  0
 13 18  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872128

   ---

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: 284.25

Molecular Weight (Monoisotopic): 284.0921

AlogP: -1.10

#Rotatable Bonds: 2

Polar Surface Area: 126.39

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.06

CX Basic pKa: 5.00

CX LogP: -1.00

CX LogD: -1.00

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.55

Np Likeness Score: 0.66

References

1. Bouton J, Furquim d'Almeida A, Maes L, Caljon G, Van Calenbergh S, Hulpia F..  (2021)  Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.,  216  [PMID:33667845] [10.1016/j.ejmech.2021.113290]

Source

Source(1):

• Scientific Literature