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

ID: ALA5281877

Max Phase: Preclinical

Molecular Formula: C19H18FN5O3

Molecular Weight: 383.38

Names and Identifiers

Canonical SMILES:  Cc1ncnc2c1c(C#Cc1ncccn1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@]1(C)F

Standard InChI:  InChI=1S/C19H18FN5O3/c1-11-15-12(4-5-14-21-6-3-7-22-14)8-25(17(15)24-10-23-11)18-19(2,20)16(27)13(9-26)28-18/h3,6-8,10,13,16,18,26-27H,9H2,1-2H3/t13-,16-,18-,19-/m1/s1

Standard InChI Key:  WJRAFSIRBQSABZ-ZQNRLITLSA-N

Molfile:  

 
     RDKit          2D

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   -1.4345   -2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -2.0244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -2.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995   -2.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -3.3936    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.6986   -2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580   -1.3097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2774   -0.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353   -0.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497   -0.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8782   -1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938   -1.7776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2763   -1.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451   -0.7151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8319   -0.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455    0.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    0.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    2.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2315   -3.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451   -3.8197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671   -4.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3790    2.8838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782    3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365    4.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484    3.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531    2.8853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0
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  5  1  1  0
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  5  7  1  1
  4  8  1  1
  8  9  1  0
  9 10  2  0
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 10 18  1  0
 18 19  3  0
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  2 21  1  1
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  1 23  1  6
 24 20  2  0
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 26 25  2  0
 27 26  1  0
 28 27  2  0
 20 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281877

   ---

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: 383.38

Molecular Weight (Monoisotopic): 383.1394

AlogP: 0.91

#Rotatable Bonds: 2

Polar Surface Area: 106.18

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: 3.91

CX LogP: 0.83

CX LogD: 0.83

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 0.15

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