4-Hydroxymethylphenyl beta-D-glucopyranoside-6-sulfate

ID: ALA4094564

PubChem CID: 137653557

Max Phase: Preclinical

Molecular Formula: C13H18O10S

Molecular Weight: 366.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)OC[C@H]1O[C@@H](Oc2ccc(CO)cc2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C13H18O10S/c14-5-7-1-3-8(4-2-7)22-13-12(17)11(16)10(15)9(23-13)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:  SJWCDOCGXAHYMU-UJPOAAIJSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   30.1989  -15.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7945  -16.6203    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.6115  -16.6157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7986  -19.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7986  -19.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5039  -20.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2091  -19.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2091  -19.0761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5039  -18.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5039  -17.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7962  -17.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5039  -21.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0915  -20.3029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0897  -18.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9163  -20.3029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6246  -19.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3300  -20.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0379  -19.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0395  -19.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3274  -18.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6225  -19.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0885  -16.2118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7472  -18.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4549  -19.0810    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
M  END

Alternative Forms

1. Parent:

   

   ALA4094564

   ---

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: -2.00

CX Basic pKa: ┄

CX LogP: -3.16

CX LogD: -3.69

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.36

Np Likeness Score: 1.73

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