Sodium salt 5-acetylamino-4-amino-2-(3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethoxy)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylate

ID: ALA3215317

PubChem CID: 90664032

Max Phase: Preclinical

Molecular Formula: C17H29N2NaO13

Molecular Weight: 470.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H30N2O13.Na/c1-5(21)19-9-6(18)2-17(16(28)29,32-14(9)10(23)7(22)3-20)30-4-8-11(24)12(25)13(26)15(27)31-8;/h6-15,20,22-27H,2-4,18H2,1H3,(H,19,21)(H,28,29);/q;+1/p-1/t6-,7-,8+,9-,10-,11+,12+,13+,14-,15+,17-;/m1./s1

Standard InChI Key:  SOFXLGQZUIHYCF-VUHWHSBOSA-M

Molfile:  

     RDKit          2D

 35 35  0  0  0  0  0  0  0  0999 V2000
    4.7133    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.3306    0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -0.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306   -1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0431    3.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2186    3.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    1.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803    2.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -0.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8313    2.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685    1.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306   -2.2477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0567    0.9557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -2.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807    1.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    0.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -3.4852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4305    3.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7815    3.8407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0983   -1.4227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    2.3838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3048    2.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -1.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -2.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -3.4852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0983   -2.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -1.8352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -1.8352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  2  1  0
  5 15  1  0
  6  7  1  0
  7 11  1  0
 12  8  1  0
  9  8  1  0
 10  2  1  0
 11 12  1  0
 12 19  1  6
  3 13  1  1
  2 14  1  6
 15 10  1  0
  5 16  1  6
  2 17  1  1
 18 16  1  0
 19 17  1  0
 13 20  1  0
 21 14  1  0
 22 14  2  0
 23 18  2  0
  6 24  1  1
  7 25  1  1
 15 26  1  6
 11 27  1  1
  9 28  1  6
 13 29  1  6
 20 30  1  1
 31 32  1  0
 20 32  1  0
 33 18  1  0
 20 34  1  6
 13 35  1  1
  3  5  1  0
  6  9  1  0
M  CHG  2   1   1  21  -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: 470.43

Molecular Weight (Monoisotopic): 470.1748

AlogP: -6.08

#Rotatable Bonds: 8

Polar Surface Area: 261.72

Molecular Species: ZWITTERION

HBA: 13

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.85

CX Basic pKa: 8.93

CX LogP: -7.70

CX LogD: -7.72

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.16

Np Likeness Score: 1.60

References

1. Sabesan S.  (1994)  Synthesis and neuraminidase inhibition studies of 4-azido, amino, and acetamido substituted sialosides,  4  (20): [10.1016/S0960-894X(01)80409-1]

Source

Source(1):

• Scientific Literature