2-bromo-4,5,6-trichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole

ID: ALA1650581

PubChem CID: 53323191

Max Phase: Preclinical

Molecular Formula: C18H16BrCl3N2O7

Molecular Weight: 558.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC[C@H]1O[C@@H](n2c(Br)nc3c(Cl)c(Cl)c(Cl)cc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C18H16BrCl3N2O7/c1-6(25)28-5-11-15(29-7(2)26)16(30-8(3)27)17(31-11)24-10-4-9(20)12(21)13(22)14(10)23-18(24)19/h4,11,15-17H,5H2,1-3H3/t11-,15-,16-,17-/m1/s1

Standard InChI Key:  IXBNBIINIMMUIN-GAEVZRCVSA-N

Molfile:  

     RDKit          2D

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   -0.6934   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -1.5354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -2.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933   -1.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173   -0.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1790   -1.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2660   -2.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931    1.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3943    0.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6794   -0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6812    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    1.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9656    0.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751   -0.0756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    0.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1756    1.2690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1382    0.5972    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.1077    1.4207    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.1091   -0.2309    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781   -3.2577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423   -0.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8496    0.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600   -0.7818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1526   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8537   -3.0378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4254   -2.9926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6950   -2.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4070   -3.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998   -2.0244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6836    2.2461    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  8  1  1
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  3  4  1  0
 16 18  1  0
  4  5  1  0
  9 19  1  0
  9 10  2  0
 10 20  1  0
  1 15  1  1
  5  1  1  0
  8 21  1  0
 10 11  1  0
  6 22  1  0
 11 14  2  0
 22 23  1  0
 22 24  2  0
 13 12  2  0
  7 25  1  0
 12  9  1  0
 25 26  2  0
 13 14  1  0
 25 27  1  0
  5  6  1  6
 21 28  1  0
  1  2  1  0
 28 29  1  0
  4  7  1  6
 28 30  2  0
 12 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650581

   [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-bromo-4,5,6-trichlorobenzimidazol-1-yl)oxolan-2-yl]methyl acetate

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: 558.60

Molecular Weight (Monoisotopic): 555.9206

AlogP: 4.08

#Rotatable Bonds: 5

Polar Surface Area: 105.95

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.42

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: 0.55

References

1. Hwang JS, Schilf R, Drach JC, Townsend LB, Bogner E..  (2009)  Susceptibilities of human cytomegalovirus clinical isolates and other herpesviruses to new acetylated, tetrahalogenated benzimidazole D-ribonucleosides.,  53  (12): [PMID:19786605] [10.1128/aac.00809-09]

Source

Source(1):

• Scientific Literature