(2S,3R,4R,6R)-2-(5-((2,3-dihydrobenzofuran-5-yl)methyl)-2-hydroxy-4-methoxyphenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

ID: ALA4794246

PubChem CID: 162672617

Max Phase: Preclinical

Molecular Formula: C22H24F2O7

Molecular Weight: 438.42

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)CCO2

Standard InChI:  InChI=1S/C22H24F2O7/c1-29-17-9-15(26)14(20-19(27)21(28)22(23,24)18(10-25)31-20)8-13(17)7-11-2-3-16-12(6-11)4-5-30-16/h2-3,6,8-9,18-21,25-28H,4-5,7,10H2,1H3/t18-,19+,20+,21-/m1/s1

Standard InChI Key:  GFLPLGDXQJVIEY-IVAOSVALSA-N

Molfile:  

 
     RDKit          2D

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   38.7748  -13.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4842  -13.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4842  -12.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7748  -12.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1931  -12.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7748  -14.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   40.8963  -12.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6047  -12.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6076  -11.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8961  -11.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1906  -11.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3110  -12.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0201  -12.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7223  -12.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7228  -11.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0171  -11.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4341  -11.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4347  -12.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2115  -12.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.6911  -11.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.2106  -11.2194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3159  -11.0513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3172  -10.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4820  -11.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7  9  1  1
  5 10  1  1
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  6 12  1  6
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  9 14  2  0
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 20 21  2  0
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 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
 16 29  1  0
 29 30  1  0
 18 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794246

   ---

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: 438.42

Molecular Weight (Monoisotopic): 438.1490

AlogP: 1.72

#Rotatable Bonds: 5

Polar Surface Area: 108.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.24

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: 1.10

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