(2R,3R,4R,5R)-2-(2-bromo-5,6-dichloro-1H-benzo[d]imidazol-1-yl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA515144

Cas Number: 217950-62-4

PubChem CID: 3006317

Max Phase: Preclinical

Molecular Formula: C12H11BrCl2N2O4

Molecular Weight: 398.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1n1c(Br)nc2cc(Cl)c(Cl)cc21

Standard InChI:  InChI=1S/C12H11BrCl2N2O4/c13-12-16-6-1-4(14)5(15)2-7(6)17(12)11-10(20)9(19)8(18)3-21-11/h1-2,8-11,18-20H,3H2/t8-,9-,10-,11-/m1/s1

Standard InChI Key:  OOAVDXDURLPULP-GWOFURMSSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.8844  -19.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8832  -19.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976  -20.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958  -18.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3108  -19.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156  -19.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1026  -20.1160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5843  -19.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0948  -18.7796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619  -20.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4087  -19.4400    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1702  -18.6308    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1688  -20.2815    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8115  -21.5100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678  -22.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8747  -22.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250  -21.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1683  -21.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7156  -20.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2318  -22.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1311  -23.2444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  7  1  1
  5  6  1  0
  8 11  1  0
  1 12  1  0
  2  3  1  0
  2 13  1  0
 10 14  1  0
  3  6  2  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
 10 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  8  9  2  0
 18 19  1  6
  9  5  1  0
 17 20  1  6
  4  1  1  0
 16 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA515144

   (2R,3R,4R,5R)-2-(2-bromo-5,6-dichloro-benzimidazol-1-yl)tetrahydropyran-3,4,5-triol

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: 398.04

Molecular Weight (Monoisotopic): 395.9279

AlogP: 1.72

#Rotatable Bonds: 1

Polar Surface Area: 87.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.41

CX Basic pKa: 3.04

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.68

Np Likeness Score: 0.24

References

1. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

Source

Source(1):

• Scientific Literature