1-Naphthyl beta-D-glucopyranoside-6-sulfate

ID: ALA4072462

PubChem CID: 137639793

Max Phase: Preclinical

Molecular Formula: C16H18O9S

Molecular Weight: 386.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(O)OC[C@H]1O[C@@H](Oc2cccc3ccccc23)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H18O9S/c17-13-12(8-23-26(20,21)22)25-16(15(19)14(13)18)24-11-7-3-5-9-4-1-2-6-10(9)11/h1-7,12-19H,8H2,(H,20,21,22)/t12-,13-,14+,15-,16-/m1/s1

Standard InChI Key:  CLHAJNGTEMFRCN-IBEHDNSVSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   22.0311  -14.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8483  -14.7053    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.4397  -13.9976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4368  -17.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4368  -17.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1421  -18.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8474  -17.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8474  -17.1651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1421  -16.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1421  -15.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8498  -15.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5575  -14.3008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7279  -16.7586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7297  -18.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1421  -19.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5545  -18.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2628  -17.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6777  -17.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9656  -16.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2607  -17.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6761  -17.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9691  -18.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9675  -19.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6721  -19.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3797  -19.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3779  -18.3931    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 22  2  0
 21 18  2  0
 18 19  1  0
 19 20  2  0
 20 17  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072462

   ---

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: 386.38

Molecular Weight (Monoisotopic): 386.0672

AlogP: -0.15

#Rotatable Bonds: 5

Polar Surface Area: 142.75

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.85

CX Basic pKa: ┄

CX LogP: -1.30

CX LogD: -1.93

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: 1.35

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