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

ID: ALA4878319

PubChem CID: 164626050

Max Phase: Preclinical

Molecular Formula: C17H16FN3O4

Molecular Weight: 345.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]cnc2c1c(-c1ccccc1)cn2[C@@H]1O[C@H](CO)[C@@H](F)[C@H]1O

Standard InChI:  InChI=1S/C17H16FN3O4/c18-13-11(7-22)25-17(14(13)23)21-6-10(9-4-2-1-3-5-9)12-15(21)19-8-20-16(12)24/h1-6,8,11,13-14,17,22-23H,7H2,(H,19,20,24)/t11-,13-,14-,17-/m1/s1

Standard InChI Key:  JMNOKJVIKYOURK-LSCFUAHRSA-N

Molfile:  

 
     RDKit          2D

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   40.4138  -11.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2310  -11.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4854  -10.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8224  -10.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1636  -10.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9326  -12.2292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.7105  -12.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3863  -10.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2629  -10.5405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.2161   -9.7405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.3333   -9.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5161   -9.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5847  -10.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9189  -11.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9987  -11.8304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.7433  -12.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4091  -11.6933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.3304  -10.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9940  -10.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.8103   -9.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6239   -9.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1049   -8.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7736   -7.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9565   -7.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4791   -8.3620    0.0000 C   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
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 11 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878319

   ---

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: 345.33

Molecular Weight (Monoisotopic): 345.1125

AlogP: 0.98

#Rotatable Bonds: 3

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: 9.75

CX Basic pKa: 1.66

CX LogP: 0.87

CX LogD: 0.87

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: 0.31

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