N-((6S,7S,8R,8aS,Z)-3-(Butylimino)-7,8-dihydroxyhexahydro-3H-thiazolo[3,4-a]pyridin-6-yl)acetamide

ID: ALA3955165

PubChem CID: 134145120

Max Phase: Preclinical

Molecular Formula: C13H23N3O3S

Molecular Weight: 301.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC/N=C1\SC[C@@H]2[C@@H](O)[C@@H](O)[C@@H](NC(C)=O)CN12

Standard InChI:  InChI=1S/C13H23N3O3S/c1-3-4-5-14-13-16-6-9(15-8(2)17)11(18)12(19)10(16)7-20-13/h9-12,18-19H,3-7H2,1-2H3,(H,15,17)/b14-13-/t9-,10+,11-,12+/m0/s1

Standard InChI Key:  LCHTZTHSQYIVAB-NWUCSGIWSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.4175   -8.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175   -9.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1229   -9.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1229   -8.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1172   -7.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7050   -8.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -9.9286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9889   -9.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807   -9.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9871   -8.6992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8284   -8.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352   -9.5166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6118   -9.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -9.1008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6049   -8.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688  -10.5404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6686  -10.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2155  -10.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0153  -10.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5581   -9.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7961   -7.8817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3 12  1  0
 11  4  1  0
  4  5  1  6
  1  6  1  6
  2  7  1  6
  7  8  1  0
  8  9  1  0
  8 10  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 11 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3955165

   ---

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: 301.41

Molecular Weight (Monoisotopic): 301.1460

AlogP: -0.20

#Rotatable Bonds: 4

Polar Surface Area: 85.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.15

CX Basic pKa: 7.45

CX LogP: -0.22

CX LogD: -0.55

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.63

Np Likeness Score: 0.16

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