4-oxo-5-bromo-N7-(3'-deoxy-3'-fluoro-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

ID: ALA4871965

PubChem CID: 164622998

Max Phase: Preclinical

Molecular Formula: C11H11BrFN3O4

Molecular Weight: 348.13

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]cnc2c1c(Br)cn2[C@@H]1O[C@H](CO)[C@@H](F)[C@H]1O

Standard InChI:  InChI=1S/C11H11BrFN3O4/c12-4-1-16(9-6(4)10(19)15-3-14-9)11-8(18)7(13)5(2-17)20-11/h1,3,5,7-8,11,17-18H,2H2,(H,14,15,19)/t5-,7-,8-,11-/m1/s1

Standard InChI Key:  ZMNKGGRWGFVBMJ-IOSLPCCCSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   16.0623  -11.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8873  -11.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1441  -10.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4748   -9.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8098  -10.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5765  -11.8084    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.3715  -11.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0251  -10.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9290  -10.1036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8531   -9.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0096   -9.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1847   -9.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2635  -10.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5913  -10.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6718  -11.4058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4236  -11.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0958  -11.2673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0163  -10.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6863   -9.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4954   -8.6539    0.0000 Br  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
 18 19  2  0
 11 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871965

   ---

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: 348.13

Molecular Weight (Monoisotopic): 346.9917

AlogP: 0.08

#Rotatable Bonds: 2

Polar Surface Area: 100.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.66

CX Basic pKa: 1.72

CX LogP: -0.01

CX LogD: -0.01

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: 0.49

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