(4-Phenyl-1H-1,2,3-triazol-1-yl)beta-D-glucopyranoside-6-sulfate

ID: ALA4099388

PubChem CID: 137660461

Max Phase: Preclinical

Molecular Formula: C14H17N3O8S

Molecular Weight: 387.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)OC[C@H]1O[C@@H](n2cc(-c3ccccc3)nn2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H17N3O8S/c18-11-10(7-24-26(21,22)23)25-14(13(20)12(11)19)17-6-9(15-16-17)8-4-2-1-3-5-8/h1-6,10-14,18-20H,7H2,(H,21,22,23)/t10-,11-,12+,13-,14-/m1/s1

Standard InChI Key:  NVJSPLULSKCIAS-RKQHYHRCSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   30.5332   -2.0100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3504   -2.0100    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.9418   -1.3023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9389   -4.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9389   -5.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6442   -5.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3495   -5.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3495   -4.4698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6442   -4.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6442   -3.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3519   -2.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0596   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2300   -4.0633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2318   -5.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6442   -6.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0566   -5.6966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1419   -6.5088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9410   -6.6799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3506   -5.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8046   -5.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1586   -5.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6376   -6.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4497   -6.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7839   -5.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2998   -5.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4894   -5.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
 10 11  1  0
 11  2  1  0
  2 12  1  0
  4 13  1  6
  5 14  1  1
  6 15  1  6
  7 16  1  1
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099388

   ---

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: 387.37

Molecular Weight (Monoisotopic): 387.0736

AlogP: -1.26

#Rotatable Bonds: 5

Polar Surface Area: 164.23

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -1.87

CX Basic pKa: ┄

CX LogP: -1.83

CX LogD: -2.68

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: 0.37

References

1. Liu C, Dunaway-Mariano D, Mariano PS..  (2017)  Rational design of reversible inhibitors for trehalose 6-phosphate phosphatases.,  128  [PMID:28192710] [10.1016/j.ejmech.2017.02.001]

Source

Source(1):

• Scientific Literature