1-beta-D-Ribofuranosyl-2,4-diamino-5-fluoropyrimidinium Chloride

ID: ALA3250415

PubChem CID: 90674440

Max Phase: Preclinical

Molecular Formula: C9H14ClFN4O4

Molecular Weight: 261.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)[n+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)cc1F.[Cl-]

Standard InChI:  InChI=1S/C9H13FN4O4.ClH/c10-3-1-14(9(12)13-7(3)11)8-6(17)5(16)4(2-15)18-8;/h1,4-6,8,15-17H,2H2,(H3,11,12,13);1H/t4-,5-,6-,8-;/m1./s1

Standard InChI Key:  PGRSGAJVJHQKMY-HCXTZZCQSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   20.6073   -3.1408    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.6425   -2.4268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6413   -3.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3494   -3.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0590   -3.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0562   -2.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3476   -2.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3452   -1.2007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7624   -2.0119    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.3492   -4.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6866   -4.9516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9390   -5.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7562   -5.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0088   -4.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7860   -4.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2364   -6.3903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4585   -6.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6458   -6.3043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333   -3.6543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  2  2  0
  7  8  1  0
  6  9  1  0
 10  4  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 14 15  1  6
 13 16  1  6
 12 17  1  1
 17 18  1  0
  3 19  1  0
M  CHG  2   1  -1   4   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 261.23

Molecular Weight (Monoisotopic): 261.0994

AlogP: -2.72

#Rotatable Bonds: 2

Polar Surface Area: 138.73

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.72

CX Basic pKa: ┄

CX LogP: -6.41

CX LogD: -6.41

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.36

Np Likeness Score: 0.80

References

1. Cook AF..  (1977)  Fluorinated Pyrimidine nucleosides. 1. Synthesis of a nitrogen analogue of the antitumor agent 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine hydrochloride.,  20  (3): [PMID:66315] [10.1021/jm00213a006]

Source

Source(1):

• Scientific Literature