2-amino-5,6-difluoro-1-(beta-D-ribofuranosyl)benzimidazole

ID: ALA4093502

PubChem CID: 137654244

Max Phase: Preclinical

Molecular Formula: C12H13F2N3O4

Molecular Weight: 301.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2cc(F)c(F)cc2n1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H13F2N3O4/c13-4-1-6-7(2-5(4)14)17(12(15)16-6)11-10(20)9(19)8(3-18)21-11/h1-2,8-11,18-20H,3H2,(H2,15,16)/t8-,9-,10-,11-/m1/s1

Standard InChI Key:  XLDZMAQPUAKWEV-GWOFURMSSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    5.6192   -5.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4451   -5.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7008   -4.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0300   -4.2331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677   -4.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9314   -6.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1312   -6.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5820   -4.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4066   -3.6607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4869   -4.4692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1575   -4.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8270   -4.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7483   -3.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5718   -3.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9829   -2.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5757   -2.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7490   -2.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375   -2.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1583   -5.7756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3334   -1.5434    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9875   -1.5433    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  2  6  1  6
  1  7  1  6
  5  8  1  1
  8  9  1  0
  3 10  1  1
 10 11  1  0
 11 12  2  0
 12 14  1  0
 13 10  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 11 19  1  0
 17 20  1  0
 16 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4093502

   ---

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: 301.25

Molecular Weight (Monoisotopic): 301.0874

AlogP: -0.49

#Rotatable Bonds: 2

Polar Surface Area: 113.76

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 7.89

CX LogP: -0.16

CX LogD: -0.72

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.59

Np Likeness Score: 0.24

References

1. Kharitonova MI, Denisova AO, Andronova VL, Kayushin AL, Konstantinova ID, Kotovskaya SK, Galegov GA, Charushin VN, Miroshnikov AI..  (2017)  New modified 2-aminobenzimidazole nucleosides: Synthesis and evaluation of their activity against herpes simplex virus type 1.,  27  (11): [PMID:28408228] [10.1016/j.bmcl.2017.03.100]

Source

Source(1):

• Scientific Literature