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

ID: ALA5286612

Max Phase: Preclinical

Molecular Formula: C21H21FN4O3

Molecular Weight: 396.42

Names and Identifiers

Canonical SMILES:  Cc1cccnc1C#Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@@]2(C)F)c2ncnc(C)c12

Standard InChI:  InChI=1S/C21H21FN4O3/c1-12-5-4-8-23-15(12)7-6-14-9-26(19-17(14)13(2)24-11-25-19)20-21(3,22)18(28)16(10-27)29-20/h4-5,8-9,11,16,18,20,27-28H,10H2,1-3H3/t16-,18-,20-,21-/m1/s1

Standard InChI Key:  KMMPOGXIRQFKQD-KRZXBLKESA-N

Molfile:  

 
     RDKit          2D

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   -1.1796   -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
    0.0579   -1.3097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    2.0454    0.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3353    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3783    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
    1.0483    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
   -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
   -1.0935    2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 26  1  1
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  1 28  1  6
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5286612

   ---

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: 396.42

Molecular Weight (Monoisotopic): 396.1598

AlogP: 1.82

#Rotatable Bonds: 2

Polar Surface Area: 93.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: 4.36

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: 0.08

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