(2S,3R,4R,6R)-2-(4-chloro-2-hydroxy-5-(3-methoxybenzyl)phenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

ID: ALA4779277

PubChem CID: 162662492

Max Phase: Preclinical

Molecular Formula: C20H21ClF2O6

Molecular Weight: 430.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(Cc2cc([C@@H]3O[C@H](CO)C(F)(F)[C@H](O)[C@H]3O)c(O)cc2Cl)c1

Standard InChI:  InChI=1S/C20H21ClF2O6/c1-28-12-4-2-3-10(6-12)5-11-7-13(15(25)8-14(11)21)18-17(26)19(27)20(22,23)16(9-24)29-18/h2-4,6-8,16-19,24-27H,5,9H2,1H3/t16-,17+,18+,19-/m1/s1

Standard InChI Key:  JEYGSKOWKIRJAU-YDZRNGNQSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   14.3669  -23.8843    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7837  -23.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9620  -23.1698    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.7837  -22.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4931  -23.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2025  -23.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2025  -22.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4931  -21.9403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9114  -21.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4931  -24.4043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0707  -21.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9097  -23.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0683  -21.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6146  -22.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3230  -21.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3259  -21.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6144  -20.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9089  -21.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0293  -22.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7384  -21.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4406  -22.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1492  -21.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1524  -21.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4411  -20.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7354  -21.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8553  -22.3799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5646  -21.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0342  -20.7296    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.2003  -20.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  1  0
  4  8  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  5 10  1  1
  4 11  1  1
  6 12  1  6
 11 13  1  0
  9 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  9  1  0
 15 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 26 27  1  0
 16 28  1  0
 18 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4779277

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 430.83

Molecular Weight (Monoisotopic): 430.0995

AlogP: 2.43

#Rotatable Bonds: 5

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.53

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 0.77

References

1. Xu G,Du F,Kuo GH,Xu JZ,Liang Y,Demarest K,Gaul MD.  (2020)  5,5-Difluoro- and 5-Fluoro-5-methyl-hexose-based C-Glucosides as potent and orally bioavailable SGLT1 and SGLT2 dual inhibitors.,  30  (17): [PMID:32738984] [10.1016/j.bmcl.2020.127387]

Source

Source(1):

• Scientific Literature