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

ID: ALA3895004

PubChem CID: 134137148

Max Phase: Preclinical

Molecular Formula: C16H23N3O4S

Molecular Weight: 353.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1CN(C(=S)NCc2ccccc2)[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H23N3O4S/c1-10(21)18-12-8-19(13(9-20)15(23)14(12)22)16(24)17-7-11-5-3-2-4-6-11/h2-6,12-15,20,22-23H,7-9H2,1H3,(H,17,24)(H,18,21)/t12-,13+,14-,15+/m0/s1

Standard InChI Key:  VVGBGYHXZAPMMS-LJISPDSOSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   21.4327   -5.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4327   -6.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1421   -7.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8515   -6.6490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8515   -5.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1421   -5.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1421   -4.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197   -5.4211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7215   -7.0627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0090   -6.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2978   -7.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0078   -5.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5645   -5.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2752   -5.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5628   -7.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5616   -7.8840    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.2752   -6.6510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9823   -7.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6947   -6.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4077   -7.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1197   -6.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1198   -5.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4020   -5.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6930   -5.8336    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  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3895004

   ---

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: 353.44

Molecular Weight (Monoisotopic): 353.1409

AlogP: -1.04

#Rotatable Bonds: 4

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: 13.07

CX Basic pKa: ┄

CX LogP: -1.06

CX LogD: -1.06

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: -0.04

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