(2R,3R,4R,5R)-5-(5-ethynyl-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

ID: ALA5279697

Max Phase: Preclinical

Molecular Formula: C15H16FN3O3

Molecular Weight: 305.31

Names and Identifiers

Canonical SMILES:  C#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@@]2(C)F)c2ncnc(C)c12

Standard InChI:  InChI=1S/C15H16FN3O3/c1-4-9-5-19(13-11(9)8(2)17-7-18-13)14-15(3,16)12(21)10(6-20)22-14/h1,5,7,10,12,14,20-21H,6H2,2-3H3/t10-,12-,14-,15-/m1/s1

Standard InChI Key:  QEFSUPDQKFPVBA-PZTHBURQSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.7671   -2.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4346   -1.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796   -0.7877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -0.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995   -1.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579   -0.0731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    0.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8782    0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320    1.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452    0.5215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2764   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -0.5410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455    1.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317   -1.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4452   -2.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671   -2.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -2.1570    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6987   -1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    2.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    2.8827    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
  4  6  1  1
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  9 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 10 14  1  0
 11 15  1  0
  2 16  1  1
 16 17  1  0
  1 18  1  6
  5 19  1  0
  5 20  1  1
  8 21  1  0
 21 22  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279697

   ---

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: 305.31

Molecular Weight (Monoisotopic): 305.1176

AlogP: 0.70

#Rotatable Bonds: 2

Polar Surface Area: 80.40

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: 3.93

CX LogP: 0.41

CX LogD: 0.41

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.80

Np Likeness Score: 0.35

References

1. Yao G, Yu J, Lin C, Zhu Y, Duan A, Li M, Yuan J, Zhang J..  (2022)  Design, synthesis, and biological evaluation of novel 2'-methyl-2'-fluoro-6-methyl-7-alkynyl-7-deazapurine nucleoside analogs as anti-Zika virus agents.,  234  [PMID:35306290] [10.1016/j.ejmech.2022.114275]

Source

Source(1):

• Scientific Literature