1-((2R,3R,4R,5R)-3-bromo-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

ID: ALA4559279

PubChem CID: 126618115

Max Phase: Preclinical

Molecular Formula: C9H10BrFN2O5

Molecular Weight: 325.09

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@]2(F)Br)c(=O)[nH]1

Standard InChI:  InChI=1S/C9H10BrFN2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h1-2,4,6-7,14,16H,3H2,(H,12,15,17)/t4-,6-,7-,9+/m1/s1

Standard InChI Key:  IERCXLRPNHKJCP-HCWSKCQFSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   11.3334   -4.4987    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.6276   -4.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6266   -4.9056    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.8145   -4.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8861   -3.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2231   -2.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5644   -3.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6643   -3.0619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3638   -3.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0774   -3.0963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0981   -2.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3990   -1.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6792   -2.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8154   -1.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3453   -4.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7871   -3.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6168   -2.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3333   -4.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  4  1  0
  5  8  1  1
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 11 14  2  0
  9 15  2  0
  7 16  1  1
 16 17  1  0
  4 18  1  6
  2  3  1  0
  2  1  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4559279

   ---

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: 325.09

Molecular Weight (Monoisotopic): 323.9757

AlogP: -1.15

#Rotatable Bonds: 2

Polar Surface Area: 104.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: ┄

CX LogP: -0.54

CX LogD: -0.54

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.60

Np Likeness Score: 0.92

References

1. Ovadia R, Khalil A, Li H, De Schutter C, Mengshetti S, Zhou S, Bassit L, Coats SJ, Amblard F, Schinazi RF..  (2019)  Synthesis and anti-HCV activity of β-d-2'-deoxy-2'-α-chloro-2'-β-fluoro and β-d-2'-deoxy-2'-α-bromo-2'-β-fluoro nucleosides and their phosphoramidate prodrugs.,  27  (4): [PMID:30655167] [10.1016/j.bmc.2019.01.005]

Source

Source(1):

• Scientific Literature