4-n-Hexylphenyl alpha-D-glucopyranoside-6-sulfate

ID: ALA4096324

PubChem CID: 137655730

Max Phase: Preclinical

Molecular Formula: C18H28O9S

Molecular Weight: 420.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCc1ccc(O[C@H]2O[C@H](COS(=O)(=O)O)[C@@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C18H28O9S/c1-2-3-4-5-6-12-7-9-13(10-8-12)26-18-17(21)16(20)15(19)14(27-18)11-25-28(22,23)24/h7-10,14-21H,2-6,11H2,1H3,(H,22,23,24)/t14-,15-,16+,17-,18+/m1/s1

Standard InChI Key:  PFVWZOZQBSGDKK-SFFUCWETSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   16.4140   -8.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0095   -9.5628    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.8265   -9.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0136  -12.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0136  -12.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7189  -13.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4242  -12.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4242  -12.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7189  -11.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7189  -10.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0112  -10.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7189  -14.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3065  -13.2453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3047  -11.6120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1313  -13.2453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8396  -12.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5451  -13.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2529  -12.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2545  -12.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5424  -11.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8375  -12.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3035   -9.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9623  -11.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6700  -12.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3777  -11.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0854  -12.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7931  -11.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5008  -12.0238    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
  6 12  1  6
  5 13  1  1
  4 14  1  6
  7 15  1  6
 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
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096324

   ---

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: 420.48

Molecular Weight (Monoisotopic): 420.1454

AlogP: 0.82

#Rotatable Bonds: 10

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: -1.96

CX Basic pKa: ┄

CX LogP: 0.37

CX LogD: -0.18

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 1.48

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