(2S,3R,4R,6R)-2-(5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-2-hydroxy-4-methoxyphenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

ID: ALA4753564

PubChem CID: 162653502

Max Phase: Preclinical

Molecular Formula: C22H24F2O8

Molecular Weight: 454.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(O)c([C@@H]2O[C@H](CO)C(F)(F)[C@H](O)[C@H]2O)cc1Cc1ccc2c(c1)OCCO2

Standard InChI:  InChI=1S/C22H24F2O8/c1-29-16-9-14(26)13(20-19(27)21(28)22(23,24)18(10-25)32-20)8-12(16)6-11-2-3-15-17(7-11)31-5-4-30-15/h2-3,7-9,18-21,25-28H,4-6,10H2,1H3/t18-,19+,20+,21-/m1/s1

Standard InChI Key:  BRHAXCOPFBDPDS-IVAOSVALSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   13.9624  -13.9046    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3793  -13.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5576  -13.1902    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3793  -12.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0887  -13.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7981  -13.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7981  -12.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0887  -11.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5070  -11.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0887  -14.4247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6662  -11.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5052  -13.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638  -11.1456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2101  -12.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186  -11.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9214  -11.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2099  -10.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5044  -11.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6249  -12.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3340  -11.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0361  -12.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0367  -10.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3310  -11.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7479  -11.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7434  -11.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4424  -12.3940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1504  -11.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1550  -11.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4515  -10.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6298  -10.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6311   -9.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7959  -10.7480    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 25  1  0
 24 22  1  0
 22 23  2  0
 23 20  1  0
 24 25  2  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 16 30  1  0
 30 31  1  0
 18 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4753564

   ---

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: 454.42

Molecular Weight (Monoisotopic): 454.1439

AlogP: 1.55

#Rotatable Bonds: 5

Polar Surface Area: 117.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.23

CX Basic pKa: ┄

CX LogP: 1.69

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: 1.01

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