4-C-p-Methoxyphenyl-1,4-dideoxy-1,4-imino-L-arabinitol

ID: ALA5202712

PubChem CID: 168293946

Max Phase: Preclinical

Molecular Formula: C12H17NO4

Molecular Weight: 239.27

Names and Identifiers

Canonical SMILES:  COc1ccc([C@@]2(CO)NC[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C12H17NO4/c1-17-9-4-2-8(3-5-9)12(7-14)11(16)10(15)6-13-12/h2-5,10-11,13-16H,6-7H2,1H3/t10-,11+,12+/m0/s1

Standard InChI Key:  ZIJKOKJAWVSURB-QJPTWQEYSA-N

Molfile:  

 
     RDKit          2D

 17 18  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
   -2.7374   -0.7943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -0.2115    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
 13 16  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202712

   ---

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: 239.27

Molecular Weight (Monoisotopic): 239.1158

AlogP: -0.79

#Rotatable Bonds: 3

Polar Surface Area: 81.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.11

CX Basic pKa: 8.44

CX LogP: -0.76

CX LogD: -1.84

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.56

Np Likeness Score: 0.67

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