5-(4-(N-(Dimethylaminomethylene)sulfamoyl)phenyl)-3-(beta-D-glucopyranosyl)-1,2,4-triazole

ID: ALA4171734

PubChem CID: 145949851

Max Phase: Preclinical

Molecular Formula: C17H23N5O7S

Molecular Weight: 441.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)/C=N/S(=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/C17H23N5O7S/c1-22(2)8-18-30(27,28)10-5-3-9(4-6-10)16-19-17(21-20-16)15-14(26)13(25)12(24)11(7-23)29-15/h3-6,8,11-15,23-26H,7H2,1-2H3,(H,19,20,21)/b18-8+/t11-,12-,13+,14-,15-/m1/s1

Standard InChI Key:  IYHHERNTAWZJAJ-YHMJHMTRSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   24.3259  -22.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3300  -23.0134    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.0357  -22.6013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7885  -22.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0794  -23.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0794  -24.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7885  -24.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3703  -24.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3703  -25.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6612  -24.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9562  -24.5859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6612  -23.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3703  -22.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9562  -22.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9562  -22.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5351  -23.2797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0832  -22.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6746  -21.9628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8740  -22.1324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8935  -22.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2245  -23.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0363  -23.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5181  -22.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1822  -22.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3713  -22.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6636  -23.7635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4763  -23.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8091  -24.5949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6218  -24.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3291  -25.2562    0.0000 C   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
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4171734

   ---

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: 441.47

Molecular Weight (Monoisotopic): 441.1318

AlogP: -1.73

#Rotatable Bonds: 6

Polar Surface Area: 181.46

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.37

CX Basic pKa: 2.56

CX LogP: -1.35

CX LogD: -1.35

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.25

Np Likeness Score: -0.19

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