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

ID: ALA1650582

PubChem CID: 53319245

Max Phase: Preclinical

Molecular Formula: C18H16Cl4N2O7

Molecular Weight: 514.15

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H16Cl4N2O7/c1-6(25)28-5-11-15(29-7(2)26)16(30-8(3)27)17(31-11)24-10-4-9(19)12(20)13(21)14(10)23-18(24)22/h4,11,15-17H,5H2,1-3H3/t11-,15-,16-,17-/m1/s1

Standard InChI Key:  PRZLSTCCWHPKBJ-GAEVZRCVSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    9.2691   -0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0219   -1.5062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917   -1.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3558   -1.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0964   -0.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5798   -0.0472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1415   -1.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6965   -2.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5694    1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5682    0.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2831   -0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2813    1.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9966    1.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9969    0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7874   -0.0465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2757    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7869    1.2982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1007    0.6263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8548    1.4499    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -0.2018    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9844   -3.2285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4048   -0.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8121    0.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8225   -0.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1151   -2.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8162   -3.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879   -2.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2675   -2.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5555   -3.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2627   -1.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2788    2.2753    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  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
  2  3  1  0
 12 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650582

   [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4,5,6-tetrachlorobenzimidazol-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: 514.15

Molecular Weight (Monoisotopic): 511.9712

AlogP: 3.97

#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: 2.12

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: 0.60

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