4-Acetamidophenyl beta-D-glucopyranoside-6-sulfate

ID: ALA4091182

PubChem CID: 137642392

Max Phase: Preclinical

Molecular Formula: C14H19NO10S

Molecular Weight: 393.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccc(O[C@@H]2O[C@H](COS(=O)(=O)O)[C@@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C14H19NO10S/c1-7(16)15-8-2-4-9(5-3-8)24-14-13(19)12(18)11(17)10(25-14)6-23-26(20,21)22/h2-5,10-14,17-19H,6H2,1H3,(H,15,16)(H,20,21,22)/t10-,11-,12+,13-,14-/m1/s1

Standard InChI Key:  XAPTUIFBRITEGN-RKQHYHRCSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   11.9675  -16.6261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5591  -17.3428    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3839  -17.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5633  -19.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5633  -20.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2753  -21.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9874  -20.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9874  -19.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2753  -19.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2753  -18.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5608  -18.1679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2753  -21.8807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8493  -21.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8476  -19.4117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7013  -21.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4164  -20.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1287  -21.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8433  -20.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8450  -19.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1261  -19.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4144  -19.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8463  -16.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5595  -19.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5596  -18.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2741  -18.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8452  -18.1770    0.0000 O   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
  6 12  1  6
  5 13  1  1
  4 14  1  6
  7 15  1  1
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 11  2  1  0
  2 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091182

   ---

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: 393.37

Molecular Weight (Monoisotopic): 393.0730

AlogP: -1.35

#Rotatable Bonds: 6

Polar Surface Area: 171.85

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -2.03

CX Basic pKa: ┄

CX LogP: -3.18

CX LogD: -3.68

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.36

Np Likeness Score: 1.01

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