4-Amino-5-(3,4-dichlorophenyl)-N7-(3'-deoxy-3'-fluoro-beta-D-xylofuranosyl)pyrrolo[2,3-d]pyrimidine

ID: ALA4878243

PubChem CID: 164628310

Max Phase: Preclinical

Molecular Formula: C17H15Cl2FN4O3

Molecular Weight: 413.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1ccc(Cl)c(Cl)c1)cn2[C@@H]1O[C@H](CO)[C@H](F)[C@H]1O

Standard InChI:  InChI=1S/C17H15Cl2FN4O3/c18-9-2-1-7(3-10(9)19)8-4-24(16-12(8)15(21)22-6-23-16)17-14(26)13(20)11(5-25)27-17/h1-4,6,11,13-14,17,25-26H,5H2,(H2,21,22,23)/t11-,13+,14-,17-/m1/s1

Standard InChI Key:  ATIBIFWGBLOPPM-ABYLEIOUSA-N

Molfile:  

 
     RDKit          2D

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   39.4150   -5.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2363   -5.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4907   -4.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8236   -3.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1607   -4.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9297   -5.7494    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   40.7159   -5.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3793   -4.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2724   -4.0525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.2090   -3.2484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3469   -3.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5256   -3.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5983   -4.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9325   -4.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0123   -5.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.7610   -5.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4268   -5.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.3481   -4.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0159   -3.9114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8280   -2.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6457   -2.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1268   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7954   -1.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9742   -1.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4926   -1.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9434   -2.1242    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.2757   -0.6200    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  1  6  1  1
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  3  9  1  1
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 25 20  1  0
 11 20  1  0
 22 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878243

   ---

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: 413.24

Molecular Weight (Monoisotopic): 412.0505

AlogP: 2.58

#Rotatable Bonds: 3

Polar Surface Area: 106.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.30

CX Basic pKa: 6.37

CX LogP: 2.47

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: 0.10

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