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

ID: ALA4799516

PubChem CID: 146249897

Max Phase: Preclinical

Molecular Formula: C22H22F2O6S

Molecular Weight: 452.48

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)cc1Cc1cc2ccccc2s1

Standard InChI:  InChI=1S/C22H22F2O6S/c1-29-16-9-15(26)14(20-19(27)21(28)22(23,24)18(10-25)30-20)8-12(16)7-13-6-11-4-2-3-5-17(11)31-13/h2-6,8-9,18-21,25-28H,7,10H2,1H3/t18-,19+,20+,21-/m1/s1

Standard InChI Key:  GOCCTPLZCAJZLV-IVAOSVALSA-N

Molfile:  

 
     RDKit          2D

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    4.0107   -4.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0107   -3.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3013   -3.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7196   -3.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3013   -5.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1312   -3.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1340   -2.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4225   -1.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8375   -3.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5466   -3.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2895   -3.4294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6323   -2.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4321   -2.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8387   -2.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6554   -2.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0665   -2.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6550   -1.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8396   -1.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8424   -1.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8437   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085   -1.8621    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
 11 13  1  0
  9 14  2  0
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 28 23  1  0
 16 29  1  0
 29 30  1  0
 18 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4799516

   ---

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: 452.48

Molecular Weight (Monoisotopic): 452.1105

AlogP: 3.00

#Rotatable Bonds: 5

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: ┄

CX LogP: 3.19

CX LogD: 3.18

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: 0.60

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