2-acetamido-1,2-dideoxyallonojirimycin

ID: ALA3966025

PubChem CID: 71747145

Max Phase: Preclinical

Molecular Formula: C8H16N2O4

Molecular Weight: 204.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1CN[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C8H16N2O4/c1-4(12)10-5-2-9-6(3-11)8(14)7(5)13/h5-9,11,13-14H,2-3H2,1H3,(H,10,12)/t5-,6+,7-,8+/m0/s1

Standard InChI Key:  GBRAQQUMMCVTAV-FKSUSPILSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  0  0  0  0  0  0999 V2000
    3.3307   -3.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -4.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360   -4.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454   -4.4120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454   -3.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0360   -2.3525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -3.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6194   -4.8216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -4.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958   -4.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -3.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4584   -3.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1690   -3.5948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  1  8  1  6
  2  9  1  6
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  1
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3966025

   N-[(3S,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl]acetamide

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: 204.23

Molecular Weight (Monoisotopic): 204.1110

AlogP: -2.82

#Rotatable Bonds: 2

Polar Surface Area: 101.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.13

CX Basic pKa: 7.85

CX LogP: -3.17

CX LogD: -3.76

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.33

Np Likeness Score: 1.46

References

1. de la Fuente A, Rísquez-Cuadro R, Verdaguer X, García Fernández JM, Nanba E, Higaki K, Ortiz Mellet C, Riera A..  (2016)  Efficient stereoselective synthesis of 2-acetamido-1,2-dideoxyallonojirimycin (DAJNAc) and sp(2)-iminosugar conjugates: Novel hexosaminidase inhibitors with discrimination capabilities between the mature and precursor forms of the enzyme.,  121  [PMID:26564401] [10.1016/j.ejmech.2015.10.038]

Source

Source(1):

• Scientific Literature