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

ID: ALA4745086

PubChem CID: 162647818

Max Phase: Preclinical

Molecular Formula: C22H21ClF2O5S

Molecular Weight: 470.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(Cl)c(Cc2cc3ccccc3s2)cc1[C@@H]1O[C@H](CO)C(F)(F)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C22H21ClF2O5S/c1-29-16-9-15(23)12(7-13-6-11-4-2-3-5-17(11)31-13)8-14(16)20-19(27)21(28)22(24,25)18(10-26)30-20/h2-6,8-9,18-21,26-28H,7,10H2,1H3/t18-,19+,20+,21-/m1/s1

Standard InChI Key:  SDJRROXRYCTJJZ-IVAOSVALSA-N

Molfile:  

 
     RDKit          2D

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   28.5884   -3.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8790   -3.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2973   -3.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8790   -5.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   26.4541   -2.1978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   30.7088   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7117   -2.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.1242   -3.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8671   -3.3675    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.2099   -2.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0098   -2.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4163   -2.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2330   -2.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6442   -2.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2327   -1.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4173   -1.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4200   -1.8022    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.5861   -1.8002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5845   -0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 14  2  0
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 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4745086

   ---

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: 470.92

Molecular Weight (Monoisotopic): 470.0766

AlogP: 3.94

#Rotatable Bonds: 5

Polar Surface Area: 79.15

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.53

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: 0.05

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