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

ID: ALA4765201

PubChem CID: 162661726

Max Phase: Preclinical

Molecular Formula: C22H23ClF2O7

Molecular Weight: 472.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(Cl)c(Cc2ccc3c(c2)OCCO3)cc1[C@@H]1O[C@H](CO)C(F)(F)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C22H23ClF2O7/c1-29-16-9-14(23)12(6-11-2-3-15-17(7-11)31-5-4-30-15)8-13(16)20-19(27)21(28)22(24,25)18(10-26)32-20/h2-3,7-9,18-21,26-28H,4-6,10H2,1H3/t18-,19+,20+,21-/m1/s1

Standard InChI Key:  FVPRRNBELAZCQU-IVAOSVALSA-N

Molfile:  

 
     RDKit          2D

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    1.6591  -13.6240    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0760  -12.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2543  -12.9095    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4948  -12.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854  -11.6801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2037  -11.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854  -14.1440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630  -11.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3606  -10.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9069  -12.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6153  -11.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6181  -10.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9066  -10.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2011  -10.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3216  -12.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0307  -11.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7328  -12.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7334  -10.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0277  -10.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4447  -10.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4401  -11.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1391  -12.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8472  -11.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8517  -10.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1483  -10.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3265  -10.4693    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4926  -10.4673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909   -9.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  1  0
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  2  5  1  0
  5  6  1  0
  6  7  1  0
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  7  9  1  1
  5 10  1  1
  4 11  1  1
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 11 13  1  0
  9 14  2  0
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 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
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 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
 18 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4765201

   ---

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: 472.87

Molecular Weight (Monoisotopic): 472.1100

AlogP: 2.50

#Rotatable Bonds: 5

Polar Surface Area: 97.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.53

CX Basic pKa: ┄

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.61

Np Likeness Score: 0.48

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