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

ID: ALA4741816

PubChem CID: 162645479

Max Phase: Preclinical

Molecular Formula: C21H21ClF2O7

Molecular Weight: 458.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](c2cc(Cc3ccc4c(c3)OCCO4)c(Cl)cc2O)[C@H](O)[C@@H](O)C1(F)F

Standard InChI:  InChI=1S/C21H21ClF2O7/c22-13-8-14(26)12(19-18(27)20(28)21(23,24)17(9-25)31-19)7-11(13)5-10-1-2-15-16(6-10)30-4-3-29-15/h1-2,6-8,17-20,25-28H,3-5,9H2/t17-,18+,19+,20-/m1/s1

Standard InChI Key:  XXKKJTPZDCJSJW-FUMNGEBKSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   37.7022   -4.7793    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.1191   -4.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2974   -4.0649    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.1191   -3.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8285   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5379   -4.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5379   -3.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8285   -2.8354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.2468   -2.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8285   -5.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4061   -2.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2450   -4.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4037   -2.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9500   -3.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6584   -2.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6612   -2.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9497   -1.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2442   -2.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3647   -3.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0738   -2.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7759   -3.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7765   -1.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0708   -2.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4878   -2.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4832   -2.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1822   -3.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.8902   -2.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8948   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1913   -1.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.3696   -1.6247    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.5357   -1.6227    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
 18 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741816

   ---

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: 458.84

Molecular Weight (Monoisotopic): 458.0944

AlogP: 2.20

#Rotatable Bonds: 4

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: 8.53

CX Basic pKa: ┄

CX LogP: 2.45

CX LogD: 2.42

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: 0.72

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