(3R,4S,5R,6R,7S),N-(3,5,6-trihydroxy-7-hydroxymethyl-azepan-4-yl)-acetamide

ID: ALA2021441

PubChem CID: 70683401

Max Phase: Preclinical

Molecular Formula: C9H18N2O5

Molecular Weight: 234.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H18N2O5/c1-4(12)11-6-5(13)3-10-9(16-2)8(15)7(6)14/h5-10,13-15H,3H2,1-2H3,(H,11,12)/t5-,6+,7-,8+,9+/m1/s1

Standard InChI Key:  YHIONQKFAQRBHP-DMAGGPPCSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -6.0107  -19.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7540  -19.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9376  -20.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4232  -20.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5982  -20.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0839  -20.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2674  -19.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3990  -18.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7419  -20.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7812  -21.6061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2403  -21.6061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795  -20.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6528  -22.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2403  -23.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4778  -22.3206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1670  -19.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  1  1  0
  2  8  1  6
  3  9  1  6
  4 10  1  1
  5 11  1  6
  6 12  1  1
 11 13  1  0
 13 14  1  0
 13 15  2  0
  8 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2021441

   N-[(3R,4S,5R,6S,7S)-3,5,6-trihydroxy-7-methoxyazepan-4-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: 234.25

Molecular Weight (Monoisotopic): 234.1216

AlogP: -2.85

#Rotatable Bonds: 2

Polar Surface Area: 111.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: 7.51

CX LogP: -2.89

CX LogD: -3.26

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.35

Np Likeness Score: 1.46

References

1. Li H, Marcelo F, Bello C, Vogel P, Butters TD, Rauter AP, Zhang Y, Sollogoub M, Blériot Y..  (2009)  Design and synthesis of acetamido tri- and tetra-hydroxyazepanes: potent and selective beta-N-acetylhexosaminidase inhibitors.,  17  (15): [PMID:19592259] [10.1016/j.bmc.2009.06.022]

Source

Source(1):

• Scientific Literature