2-[6-(4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethylsulfanyl]-butyrate; compound with sodium

ID: ALA3215327

PubChem CID: 90664043

Max Phase: Preclinical

Molecular Formula: C17H29NaO12S

Molecular Weight: 458.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(SC[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@H](OC)O[C@H]2CO)[C@@H](O)[C@@H](O)[C@H]1O)C(=O)[O-].[Na+]

Standard InChI:  InChI=1S/C17H30O12S.Na/c1-3-8(15(24)25)30-5-7-9(19)10(20)12(22)17(28-7)29-14-6(4-18)27-16(26-2)13(23)11(14)21;/h6-14,16-23H,3-5H2,1-2H3,(H,24,25);/q;+1/p-1/t6-,7-,8?,9-,10-,11+,12-,13-,14+,16+,17-;/m0./s1

Standard InChI Key:  SDCMZALLIASHKB-LDXYOQADSA-M

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
    4.7161    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -1.0955    0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811    1.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479    1.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100   -0.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811   -0.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955    1.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334    2.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479    2.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955   -1.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811   -0.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811    2.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -3.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -2.0900    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -1.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -3.7400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -2.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245    0.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624    1.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334    0.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5245   -1.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955   -2.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624    2.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3334   -3.7400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955    2.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8100    2.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -2.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624    3.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4768   -2.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  9  1  6
  4  2  1  0
  5  3  1  0
  6  5  1  0
  7  4  1  0
  8  2  1  0
  2  9  1  6
 10 14  1  0
 11 10  1  0
 12 13  1  0
 13  8  1  0
 14  3  1  0
 15 19  1  0
 16 17  1  0
 13 17  1  1
 18 15  2  0
 19 16  1  0
  4 20  1  6
  6 21  1  1
  5 22  1  1
  7 23  1  6
 12 24  1  6
 11 25  1  1
 26 15  1  0
 14 27  1  6
 28 27  1  0
 29 19  1  0
 30 25  1  0
 31 29  1  0
 12  7  1  0
  6 11  1  0
M  CHG  2   1   1  26  -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: 458.48

Molecular Weight (Monoisotopic): 458.1458

AlogP: -3.14

#Rotatable Bonds: 9

Polar Surface Area: 195.60

Molecular Species: ACID

HBA: 12

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.78

CX Basic pKa: ┄

CX LogP: -2.32

CX LogD: -5.59

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.18

Np Likeness Score: 1.45

References

1. Fazli A, Bradley SJ, Kiefel MJ, Jolly C, Holmes IH, von Itzstein M..  (2001)  Synthesis and biological evaluation of sialylmimetics as rotavirus inhibitors.,  44  (20): [PMID:11563928] [10.1021/jm0100887]

Source

Source(1):

• Scientific Literature