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

ID: ALA4873064

PubChem CID: 164624798

Max Phase: Preclinical

Molecular Formula: C18H18ClFN4O3

Molecular Weight: 392.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2cn([C@@H]3O[C@H](CO)[C@H](F)[C@H]3O)c3ncnc(N)c23)ccc1Cl

Standard InChI:  InChI=1S/C18H18ClFN4O3/c1-8-4-9(2-3-11(8)19)10-5-24(17-13(10)16(21)22-7-23-17)18-15(26)14(20)12(6-25)27-18/h2-5,7,12,14-15,18,25-26H,6H2,1H3,(H2,21,22,23)/t12-,14+,15-,18-/m1/s1

Standard InChI Key:  TUMKXXNCBXAOJY-MJXUCMMTSA-N

Molfile:  

 
     RDKit          2D

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   28.9607  -13.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7820  -13.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0405  -12.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3735  -11.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7106  -12.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4795  -13.8140    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.2657  -13.8152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9291  -12.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8222  -12.1171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7589  -11.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8967  -11.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0754  -11.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1482  -12.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4782  -12.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5580  -13.4152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3067  -13.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9767  -13.2740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8980  -12.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5657  -11.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3738  -10.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1915  -10.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6766  -10.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3453   -9.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5240   -9.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0425   -9.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4933  -10.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8256   -8.6846    0.0000 Cl  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
  1  6  1  1
  2  7  1  6
  5  8  1  1
  3  9  1  1
  8 10  1  0
  9 14  1  0
 13 11  1  0
 11 12  2  0
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 15 16  2  0
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 20 21  2  0
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 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 11 20  1  0
 22 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873064

   ---

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: 392.82

Molecular Weight (Monoisotopic): 392.1051

AlogP: 2.23

#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: 2.38

CX LogD: 2.34

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: 0.05

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