Methyl 3-O-benzyl-alpha-D-glucopyranoside-6-sulfate

ID: ALA4101873

PubChem CID: 137661716

Max Phase: Preclinical

Molecular Formula: C14H20O9S

Molecular Weight: 364.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](COS(=O)(=O)O)[C@@H](O)[C@H](OCc2ccccc2)[C@H]1O

Standard InChI:  InChI=1S/C14H20O9S/c1-20-14-12(16)13(21-7-9-5-3-2-4-6-9)11(15)10(23-14)8-22-24(17,18)19/h2-6,10-16H,7-8H2,1H3,(H,17,18,19)/t10-,11-,12-,13+,14+/m1/s1

Standard InChI Key:  ROXSCRJFALIVNW-POQQGIQPSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.4739  -14.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911  -14.4082    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8825  -13.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796  -16.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796  -17.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849  -18.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902  -17.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902  -16.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849  -16.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849  -15.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2926  -15.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0003  -14.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707  -16.4615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725  -18.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849  -18.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9973  -18.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961  -18.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737  -18.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666  -19.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618  -18.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551  -19.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559  -20.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692  -20.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729  -20.1330    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  6
 16 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4101873

   ---

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: 364.37

Molecular Weight (Monoisotopic): 364.0828

AlogP: -0.52

#Rotatable Bonds: 7

Polar Surface Area: 131.75

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.84

CX Basic pKa: ┄

CX LogP: -1.61

CX LogD: -2.24

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.55

Np Likeness Score: 1.54

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