4-C-Phenyl-1,4-dideoxy-1,4-imino-L-arabinitol

ID: ALA5189075

PubChem CID: 168278373

Max Phase: Preclinical

Molecular Formula: C11H15NO3

Molecular Weight: 209.25

Names and Identifiers

Canonical SMILES:  OC[C@]1(c2ccccc2)NC[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H15NO3/c13-7-11(8-4-2-1-3-5-8)10(15)9(14)6-12-11/h1-5,9-10,12-15H,6-7H2/t9-,10+,11+/m0/s1

Standard InChI Key:  WOGBPTSLHJLKOL-HBNTYKKESA-N

Molfile:  

 
     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    1.1158    0.5438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5283   -0.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033   -0.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4484    0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358    0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2909   -1.4400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407   -1.4400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0775    1.4400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5628   -0.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3573   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9407   -0.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9348    0.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  6
  5  7  1  0
  4  8  1  1
  3  9  1  6
  6 10  1  0
 11  7  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
  7 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5189075

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 209.25

Molecular Weight (Monoisotopic): 209.1052

AlogP: -0.80

#Rotatable Bonds: 2

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: 8.53

CX LogP: -0.61

CX LogD: -1.76

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.51

Np Likeness Score: 0.76

References

1. Wang JZ, Cheng B, Kato A, Kise M, Shimadate Y, Jia YM, Li YX, Fleet GWJ, Yu CY..  (2022)  Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.,  233  [PMID:35255314] [10.1016/j.ejmech.2022.114230]

Source

Source(1):

• Scientific Literature