[6-(4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethylsulfanyl]-phenyl-acetate sodium

ID: ALA3215371

PubChem CID: 90664102

Max Phase: Preclinical

Molecular Formula: C21H29NaO12S

Molecular Weight: 506.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1O[C@@H](CO)[C@@H](O[C@@H]2O[C@@H](CSC(C(=O)[O-])c3ccccc3)[C@H](O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H]1O.[Na+]

Standard InChI:  InChI=1S/C21H30O12S.Na/c1-30-20-16(27)14(25)17(10(7-22)31-20)33-21-15(26)13(24)12(23)11(32-21)8-34-18(19(28)29)9-5-3-2-4-6-9;/h2-6,10-18,20-27H,7-8H2,1H3,(H,28,29);/q;+1/p-1/t10-,11-,12-,13-,14+,15-,16-,17+,18?,20+,21-;/m0./s1

Standard InChI Key:  NPFKSYVCPXULRY-KGSGJAPQSA-M

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    5.7906    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    1.4079    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224   -0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    1.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369   -0.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369   -1.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    1.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    0.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    0.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079   -1.7835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224   -2.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210    1.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079   -0.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1644   -0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500    0.6915    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1644    0.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4500   -0.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789   -0.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    1.9290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513   -2.1960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513   -0.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935    2.7540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355    1.9290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224   -3.0210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6935   -0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210   -0.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8789    1.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    0.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079   -3.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078    0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    1.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078    1.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  9  1  1
  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 17  1  0
 16 18  1  0
 17 16  1  0
 13 18  1  1
 19 15  1  0
 20 15  2  0
 21 17  1  0
  4 22  1  6
  6 23  1  6
  5 24  1  6
  7 25  1  6
 12 26  1  6
 11 27  1  6
 14 28  1  1
 29 28  1  0
 30 21  2  0
 31 21  1  0
 32 27  1  0
 33 31  2  0
 34 30  1  0
 35 34  2  0
  7 12  1  0
  6 11  1  0
 35 33  1  0
M  CHG  2   1   1  19  -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: 506.53

Molecular Weight (Monoisotopic): 506.1458

AlogP: -2.18

#Rotatable Bonds: 9

Polar Surface Area: 195.60

Molecular Species: ACID

HBA: 12

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.73

CX Basic pKa: ┄

CX LogP: -1.47

CX LogD: -4.77

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.19

Np Likeness Score: 1.16

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