4-Amino-5-fluoro-1-(2-hydroxymethyl-[1,3]dioxolan-4-yl)-1H-pyrimidin-2-one

ID: ALA2114997

PubChem CID: 5272044

Max Phase: Preclinical

Molecular Formula: C8H10FN3O4

Molecular Weight: 231.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n([C@@H]2CO[C@@H](CO)O2)cc1F

Standard InChI:  InChI=1S/C8H10FN3O4/c9-4-1-12(8(14)11-7(4)10)5-3-15-6(2-13)16-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1

Standard InChI Key:  RJKXXGNCKMQXTH-NTSWFWBYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    1.4155   -3.8386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524   -2.6895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1649   -3.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411   -3.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285   -2.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5779   -2.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3281   -4.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5288   -4.4381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5870   -5.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0666   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352   -3.9967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3614   -5.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -2.0400    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6653   -1.3781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1990   -4.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577   -5.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  1  1  0
  5  4  2  0
  6  5  1  0
  7  1  1  6
  8  7  1  0
  9 12  1  0
 10  8  1  0
 11  3  2  0
 12  7  1  0
 13  5  1  0
 14  6  1  0
 15 16  1  0
 10 16  1  1
  9 10  1  0
  6  2  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2114997

   4-amino-5-fluoro-1-[(2R,4S)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]pyrimidin-2-one

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: 231.18

Molecular Weight (Monoisotopic): 231.0655

AlogP: -1.17

#Rotatable Bonds: 2

Polar Surface Area: 99.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.85

CX Basic pKa: ┄

CX LogP: -1.12

CX LogD: -1.12

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.66

Np Likeness Score: 0.28

References

1. Lee M, Chu CK, Balakrishna Pai S, Zhu Y, Cheng Y, Chun MW, Chung WK.  (1995)  Dioxolane cytosine nucleosides as anti-hepatitis B agents,  5  (17): [10.1016/0960-894X(95)00343-R]

Source

Source(1):

• Scientific Literature