N-((3S,4S,5R,6R)-1-(Butylcarbamothioyl)-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl)acetamide

ID: ALA3936181

PubChem CID: 134148690

Max Phase: Preclinical

Molecular Formula: C13H25N3O4S

Molecular Weight: 319.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNC(=S)N1C[C@H](NC(C)=O)[C@H](O)[C@H](O)[C@H]1CO

Standard InChI:  InChI=1S/C13H25N3O4S/c1-3-4-5-14-13(21)16-6-9(15-8(2)18)11(19)12(20)10(16)7-17/h9-12,17,19-20H,3-7H2,1-2H3,(H,14,21)(H,15,18)/t9-,10+,11-,12+/m0/s1

Standard InChI Key:  ZTLWCGULEPATOC-WHOHXGKFSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    9.5669   -3.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5669   -4.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2763   -4.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9857   -4.2676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9857   -3.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2763   -3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2763   -2.2122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -3.0397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8557   -4.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1432   -4.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4320   -4.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1421   -3.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6946   -3.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4053   -3.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6928   -4.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6917   -5.5026    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.4053   -4.2696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1165   -4.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8289   -4.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5402   -4.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2526   -4.2737    0.0000 C   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
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3936181

   ---

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: 319.43

Molecular Weight (Monoisotopic): 319.1566

AlogP: -1.44

#Rotatable Bonds: 5

Polar Surface Area: 105.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: ┄

CX LogP: -1.46

CX LogD: -1.46

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.31

Np Likeness Score: 0.17

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