Sodium salt 5-acetylamino-2-(3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-ylmethylsulfanyl)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylate

ID: ALA605049

PubChem CID: 46874449

Max Phase: Preclinical

Molecular Formula: C17H28NNaO12S

Molecular Weight: 471.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](CSC2(C(=O)[O-])CC(O)C(NC(C)=O)C([C@@H](O)[C@H](O)CO)O2)[C@@H](O)[C@@H]1O.[Na+]

Standard InChI:  InChI=1S/C17H29NO12S.Na/c1-6(20)18-10-7(21)3-17(16(26)27,30-14(10)11(23)8(22)4-19)31-5-9-12(24)13(25)15(28-2)29-9;/h7-15,19,21-25H,3-5H2,1-2H3,(H,18,20)(H,26,27);/q;+1/p-1/t7?,8-,9-,10?,11+,12-,13+,14?,15+,17?;/m1./s1

Standard InChI Key:  GMMAIYWWBLQXBJ-AISVHYKFSA-M

Molfile:  

     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
    6.3500   -1.3500    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    4.3792   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -2.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5750   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375   -3.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -4.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -3.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -3.1917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -0.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -0.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -5.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4833   -5.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667   -5.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -1.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -5.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5125   -1.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9542   -5.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708   -1.7167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000   -1.0250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  2  1  0
  5 14  1  0
  6 10  1  0
  7 11  1  0
  8  2  1  0
  9  7  1  0
 10 11  1  0
 11 18  1  1
 12  3  1  0
 13  2  1  0
 14  8  1  0
 15  5  1  0
 16  2  1  0
 17 15  1  0
 18 16  1  0
 19 12  1  0
 20 13  1  0
 21 13  2  0
 22 17  2  0
  6 23  1  6
 10 24  1  6
 12 25  1  6
  9 26  1  6
 14 27  1  0
 19 28  1  1
 29 30  1  0
 30 19  1  0
 31 17  1  0
 32 26  1  0
 12 33  1  1
 19 34  1  6
  5  3  1  0
  6  9  1  0
M  CHG  2   1   1  20  -1
M  END

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: 471.48

Molecular Weight (Monoisotopic): 471.1410

AlogP: -4.04

#Rotatable Bonds: 9

Polar Surface Area: 215.47

Molecular Species: ACID

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.31

CX Basic pKa: ┄

CX LogP: -3.53

CX LogD: -6.96

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.16

Np Likeness Score: 1.54

References

1. Kiefel MJ, Beisner B, Bennett S, Holmes ID, von Itzstein M..  (1996)  Synthesis and biological evaluation of N-acetylneuraminic acid-based rotavirus inhibitors.,  39  (6): [PMID:8632438] [10.1021/jm950611f]

Source

Source(1):

• Scientific Literature