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

ID: ALA3933402

PubChem CID: 134137836

Max Phase: Preclinical

Molecular Formula: C17H33N3O4S

Molecular Weight: 375.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H33N3O4S/c1-3-4-5-6-7-8-9-18-17(25)20-10-13(19-12(2)22)15(23)16(24)14(20)11-21/h13-16,21,23-24H,3-11H2,1-2H3,(H,18,25)(H,19,22)/t13-,14+,15-,16+/m0/s1

Standard InChI Key:  OGAPJXHWULCOJW-XUWVNRHRSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
   18.1681   -3.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1681   -4.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8775   -4.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5869   -4.3171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5869   -3.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8775   -3.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8775   -2.2617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4550   -3.0892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4568   -4.7308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7444   -4.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0331   -4.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7432   -3.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2999   -3.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0105   -3.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2981   -4.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2969   -5.5521    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.0105   -4.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7177   -4.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4301   -4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1413   -4.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8538   -4.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5650   -4.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2774   -4.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9887   -4.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7011   -4.3274    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
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3933402

   ---

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: 375.54

Molecular Weight (Monoisotopic): 375.2192

AlogP: 0.12

#Rotatable Bonds: 9

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: 13.09

CX Basic pKa: ┄

CX LogP: 0.32

CX LogD: 0.32

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.29

Np Likeness Score: 0.27

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