5-(4-Sulfamoylphenyl)-3-(beta-D-glucopyranosyl)-1,2,4-triazole

ID: ALA4161126

PubChem CID: 145958916

Max Phase: Preclinical

Molecular Formula: C14H18N4O7S

Molecular Weight: 386.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(-c2n[nH]c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n2)cc1

Standard InChI:  InChI=1S/C14H18N4O7S/c15-26(23,24)7-3-1-6(2-4-7)13-16-14(18-17-13)12-11(22)10(21)9(20)8(5-19)25-12/h1-4,8-12,19-22H,5H2,(H2,15,23,24)(H,16,17,18)/t8-,9-,10+,11-,12-/m1/s1

Standard InChI Key:  ISCKPRMKXPCFLM-RMPHRYRLSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   23.8306  -15.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8347  -16.3067    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.5404  -15.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2932  -16.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5841  -16.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5841  -17.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2932  -17.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8750  -17.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8750  -18.6963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1659  -17.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4610  -17.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1659  -16.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8750  -16.2489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4610  -16.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4610  -15.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0398  -16.5730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5879  -15.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1793  -15.2561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3787  -15.4257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3982  -16.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7292  -16.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5411  -16.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0228  -16.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6869  -15.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8761  -15.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1683  -17.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  1  1
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 12 14  1  1
 14 15  1  0
  5 13  1  0
  4 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  4  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 17 20  1  0
 23  2  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4161126

   ---

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: -2.37

#Rotatable Bonds: 4

Polar Surface Area: 191.88

Molecular Species: NEUTRAL

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.27

CX Basic pKa: 0.33

CX LogP: -1.88

CX LogD: -1.89

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: -0.22

References

1. Kun S, Begum J, Kyriakis E, Stamati ECV, Barkas TA, Szennyes E, Bokor É, Szabó KE, Stravodimos GA, Sipos Á, Docsa T, Gergely P, Moffatt C, Patraskaki MS, Kokolaki MC, Gkerdi A, Skamnaki VT, Leonidas DD, Somsák L, Hayes JM..  (2018)  A multidisciplinary study of 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazole derivatives as glycogen phosphorylase inhibitors: Computation, synthesis, crystallography and kinetics reveal new potent inhibitors.,  147  [PMID:29453094] [10.1016/j.ejmech.2018.01.095]

Source

Source(1):

• Scientific Literature