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

ID: ALA2114995

PubChem CID: 5272047

Max Phase: Preclinical

Molecular Formula: C8H10BrN3O4

Molecular Weight: 292.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n([C@@H]2CO[C@@H](CO)O2)cc1Br

Standard InChI:  InChI=1S/C8H10BrN3O4/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:  YSEUJPGXPHRMRF-NTSWFWBYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    1.4250   -3.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -2.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -4.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -5.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -3.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -5.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125   -2.1792    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -1.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -4.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -5.3875    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:

   

   ALA2114995

   4-amino-5-bromo-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: 292.09

Molecular Weight (Monoisotopic): 290.9855

AlogP: -0.55

#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: -0.49

CX LogD: -0.49

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.76

Np Likeness Score: 0.55

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