4-[3''-(Aminosulfonyl)phenyl]-1-(beta-D-glucopyranosyl)-1H-1,2,3-triazole

ID: ALA3092939

PubChem CID: 72792901

Max Phase: Preclinical

Molecular Formula: C14H18N4O7S

Molecular Weight: 386.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1cccc(-c2cn([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn2)c1

Standard InChI:  InChI=1S/C14H18N4O7S/c15-26(23,24)8-3-1-2-7(4-8)9-5-18(17-16-9)14-13(22)12(21)11(20)10(6-19)25-14/h1-5,10-14,19-22H,6H2,(H2,15,23,24)/t10-,11-,12+,13-,14-/m1/s1

Standard InChI Key:  FONJWGKYSXVPEY-RKQHYHRCSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   40.4924  -11.0857    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   40.9022  -10.3697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0772  -10.3728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3503  -11.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3492  -12.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0639  -12.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7803  -12.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7775  -11.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0621  -11.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6358  -11.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3687  -10.3113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5438  -10.3289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3067  -11.1165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9834  -11.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5835  -11.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8798  -11.0826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1592  -11.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1381  -12.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8437  -12.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5704  -12.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4550  -11.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4749  -10.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4139  -12.6970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8239  -13.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2763  -12.7623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.2063  -11.4944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 10  2  0
 15 13  1  1
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  1
 21 22  1  0
 18 23  1  6
 19 24  1  1
 20 25  1  6
  8  1  1  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3092939

   3-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]benzenesulfonamide

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: 386.39

Molecular Weight (Monoisotopic): 386.0896

AlogP: -2.44

#Rotatable Bonds: 4

Polar Surface Area: 181.02

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.02

CX Basic pKa: ┄

CX LogP: -1.75

CX LogD: -1.76

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: -0.40

References

1. Carroux CJ, Rankin GM, Moeker J, Bornaghi LF, Katneni K, Morizzi J, Charman SA, Vullo D, Supuran CT, Poulsen SA..  (2013)  A prodrug approach toward cancer-related carbonic anhydrase inhibition.,  56  (23): [PMID:24200125] [10.1021/jm401163e]

Source

Source(1):

• Scientific Literature