2-(5,6-dichloro-1H-benzo[d][1,2,3]triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA3735908

PubChem CID: 275783

Max Phase: Preclinical

Molecular Formula: C11H11Cl2N3O4

Molecular Weight: 320.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC1OC(n2nnc3cc(Cl)c(Cl)cc32)C(O)C1O

Standard InChI:  InChI=1S/C11H11Cl2N3O4/c12-4-1-6-7(2-5(4)13)16(15-14-6)11-10(19)9(18)8(3-17)20-11/h1-2,8-11,17-19H,3H2

Standard InChI Key:  XUIJNCCBICNURA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560    1.3452    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560   -1.3452    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -3.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -5.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -4.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5643   -3.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5805   -2.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702   -5.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277   -6.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385   -6.5715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
  2 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  7 12  1  0
 16 17  1  0
 15 18  1  0
 14 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735908

   5,6-Dichloro-1-pentofuranosyl-1h-benzotriazole

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: 320.13

Molecular Weight (Monoisotopic): 319.0127

AlogP: 0.35

#Rotatable Bonds: 2

Polar Surface Area: 100.63

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 0.24

CX LogP: 0.85

CX LogD: 0.85

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.74

Np Likeness Score: -0.05

References

1. Loddo R, Novelli F, Sparatore A, Tasso B, Tonelli M, Boido V, Sparatore F, Collu G, Delogu I, Giliberti G, La Colla P..  (2015)  Antiviral activity of benzotriazole derivatives. 5-[4-(Benzotriazol-2-yl)phenoxy]-2,2-dimethylpentanoic acids potently and selectively inhibit Coxsackie Virus B5.,  23  (21): [PMID:26443549] [10.1016/j.bmc.2015.09.035]

Source

Source(1):

• Scientific Literature