(2S,3R,4R,6R)-2-(5-(benzo[b]thiophen-2-ylmethyl)-4-chloro-2-hydroxyphenyl)-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

ID: ALA4756083

PubChem CID: 162655886

Max Phase: Preclinical

Molecular Formula: C21H19ClF2O5S

Molecular Weight: 456.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](c2cc(Cc3cc4ccccc4s3)c(Cl)cc2O)[C@H](O)[C@@H](O)C1(F)F

Standard InChI:  InChI=1S/C21H19ClF2O5S/c22-14-8-15(26)13(19-18(27)20(28)21(23,24)17(9-25)29-19)7-11(14)6-12-5-10-3-1-2-4-16(10)30-12/h1-5,7-8,17-20,25-28H,6,9H2/t17-,18+,19+,20-/m1/s1

Standard InChI Key:  URGFAONHCWSEQV-FUMNGEBKSA-N

Molfile:  

 
     RDKit          2D

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   14.5113   -4.8082    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9282   -4.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1065   -4.0938    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9282   -3.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6376   -4.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3470   -4.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3470   -3.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6376   -2.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0559   -2.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6376   -5.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2152   -2.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0541   -4.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2128   -2.0492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7591   -3.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4675   -2.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4703   -2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7588   -1.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0533   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1738   -3.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8829   -2.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6258   -3.2189    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9686   -2.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7684   -1.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1750   -2.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9917   -2.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4028   -1.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9913   -1.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1759   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1787   -1.6536    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.3448   -1.6516    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  1  0
 21 24  1  0
 23 22  1  0
 22 20  2  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 16 29  1  0
 18 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756083

   ---

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: 456.89

Molecular Weight (Monoisotopic): 456.0610

AlogP: 3.64

#Rotatable Bonds: 4

Polar Surface Area: 90.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.45

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 3.91

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: 0.28

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