(2R,3R,4R,5R)-5-(5-(3,3-dimethylbut-1-yn-1-yl)-4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

ID: ALA5284233

Max Phase: Preclinical

Molecular Formula: C19H24FN3O3

Molecular Weight: 361.42

Names and Identifiers

Canonical SMILES:  Cc1ncnc2c1c(C#CC(C)(C)C)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@]1(C)F

Standard InChI:  InChI=1S/C19H24FN3O3/c1-11-14-12(6-7-18(2,3)4)8-23(16(14)22-10-21-11)17-19(5,20)15(25)13(9-24)26-17/h8,10,13,15,17,24-25H,9H2,1-5H3/t13-,15-,17-,19-/m1/s1

Standard InChI Key:  LJYOMDSZXYPQPV-LRCYWBKYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.7671   -2.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345   -2.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796   -1.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995   -2.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -2.9681    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6986   -2.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579   -0.8842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -0.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    0.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497    0.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8782   -0.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938   -1.3521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763   -1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451   -0.2895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8319    0.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454    1.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    2.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    2.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2315   -2.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451   -3.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671   -3.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791    3.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5489    3.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606    2.8966    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
  5  6  1  0
  5  7  1  1
  4  8  1  1
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
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 11 16  1  0
 16 17  1  0
 10 18  1  0
 18 19  3  0
 19 20  1  0
  2 21  1  1
 21 22  1  0
  1 23  1  6
 20 24  1  0
 20 25  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284233

   ---

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: 361.42

Molecular Weight (Monoisotopic): 361.1802

AlogP: 2.12

#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: 3.92

CX LogP: 2.28

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: 0.46

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