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

ID: ALA4761283

PubChem CID: 146249362

Max Phase: Preclinical

Molecular Formula: C20H21ClF2O6

Molecular Weight: 430.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2cc([C@@H]3O[C@H](CO)C(F)(F)[C@H](O)[C@H]3O)c(O)cc2Cl)cc1

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

Standard InChI Key:  VCUVOYYYEQWSEP-YDZRNGNQSA-N

Molfile:  

 
     RDKit          2D

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    2.3278  -22.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5061  -22.7447    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278  -21.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372  -23.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7466  -22.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7466  -21.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372  -21.5152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555  -21.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372  -23.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6147  -21.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537  -23.1630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123  -20.7001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1586  -21.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8670  -21.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699  -20.7120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1584  -20.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529  -20.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5734  -21.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825  -21.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9846  -21.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6932  -21.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6964  -20.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9852  -20.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2794  -20.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4050  -20.3183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1118  -20.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5782  -20.3045    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7443  -20.3025    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
 23 26  1  0
 26 27  1  0
 16 28  1  0
 18 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761283

   ---

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: 8.54

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 0.84

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