3-Sulfatomethylphenyl beta-D-glucopyranoside

ID: ALA4089918

PubChem CID: 137643730

Max Phase: Preclinical

Molecular Formula: C13H18O10S

Molecular Weight: 366.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)OCc1cccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C13H18O10S/c14-5-9-10(15)11(16)12(17)13(23-9)22-8-3-1-2-7(4-8)6-21-24(18,19)20/h1-4,9-17H,5-6H2,(H,18,19,20)/t9-,10-,11+,12-,13-/m1/s1

Standard InChI Key:  DFHIJPSFVDSBKL-UJPOAAIJSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   26.2533   -8.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0705   -8.6011    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.6655   -7.8914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6658  -11.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6647  -11.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3727  -12.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0824  -11.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0795  -11.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3709  -10.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3685   -9.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0750   -9.4201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7790   -8.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9566  -12.2844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2493  -11.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2538  -11.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5505  -10.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8401  -11.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8375  -11.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5453  -12.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5542   -9.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2638   -9.4268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1342  -10.6421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1280  -12.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5449  -13.1028    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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  2 12  1  0
  5 13  1  0
 14 13  1  1
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 16 20  1  1
 20 21  1  0
 17 22  1  6
 18 23  1  1
 19 24  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4089918

   ---

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: 366.34

Molecular Weight (Monoisotopic): 366.0621

AlogP: -1.82

#Rotatable Bonds: 6

Polar Surface Area: 162.98

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -2.08

CX Basic pKa: ┄

CX LogP: -3.22

CX LogD: -3.69

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.36

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