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

ID: ALA4756382

PubChem CID: 146249906

Max Phase: Preclinical

Molecular Formula: C23H27FO8

Molecular Weight: 450.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H27FO8/c1-23(24)19(11-25)32-21(20(27)22(23)28)14-9-13(17(29-2)10-15(14)26)7-12-3-4-16-18(8-12)31-6-5-30-16/h3-4,8-10,19-22,25-28H,5-7,11H2,1-2H3/t19-,20+,21+,22-,23-/m1/s1

Standard InChI Key:  PSGPXDNCYGGOCU-BMXMUORJSA-N

Molfile:  

 
     RDKit          2D

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   38.6639  -23.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   40.0827  -23.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3733  -22.6544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.7916  -22.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3733  -25.1183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   43.6186  -22.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3207  -23.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3213  -21.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6156  -21.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0326  -21.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0280  -22.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7270  -23.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.4350  -22.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.4396  -21.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7361  -21.4591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9144  -21.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0805  -21.4416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9157  -20.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
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  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
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 15 16  2  0
 16 17  1  0
 17 18  2  0
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 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
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756382

   ---

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: 450.46

Molecular Weight (Monoisotopic): 450.1690

AlogP: 1.64

#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: 1.53

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: 1.05

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