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

ID: ALA2115099

PubChem CID: 5272046

Max Phase: Preclinical

Molecular Formula: C8H10ClN3O4

Molecular Weight: 247.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n([C@@H]2CO[C@@H](CO)O2)cc1Cl

Standard InChI:  InChI=1S/C8H10ClN3O4/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:  FHQBEXAIBWHLBV-NTSWFWBYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    6.1125   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -4.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -0.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -2.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875   -2.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -4.5375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -0.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -0.6667    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
  2  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115099

   4-amino-5-chloro-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: 247.64

Molecular Weight (Monoisotopic): 247.0360

AlogP: -0.66

#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: -0.66

CX LogD: -0.66

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.72

Np Likeness Score: 0.37

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