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

ID: ALA4743055

PubChem CID: 162647060

Max Phase: Preclinical

Molecular Formula: C22H22ClFO5S

Molecular Weight: 452.93

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H22ClFO5S/c1-22(24)18(10-25)29-20(19(27)21(22)28)14-8-12(15(23)9-16(14)26)7-13-6-11-4-2-3-5-17(11)30-13/h2-6,8-9,18-21,25-28H,7,10H2,1H3/t18-,19+,20+,21-,22-/m1/s1

Standard InChI Key:  FWCUAIKEJANOBE-CDJZJNNCSA-N

Molfile:  

 
     RDKit          2D

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   15.0325   -4.9373    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.4533   -4.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6238   -4.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4533   -3.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1695   -4.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8856   -4.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8856   -3.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1695   -2.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6012   -2.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1695   -5.4622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7336   -2.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5994   -4.6382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7311   -2.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3111   -3.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0263   -2.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0291   -2.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3108   -1.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5986   -2.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7393   -3.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4551   -2.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7442   -1.7526    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.8834   -1.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2051   -3.3329    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5416   -2.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3490   -2.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7595   -2.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5839   -2.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9989   -2.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5835   -1.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7604   -1.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  2  1  0
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  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
 16 21  1  0
 18 22  1  0
 20 23  1  0
 23 26  1  0
 25 24  1  0
 24 20  2  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743055

   ---

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: 452.93

Molecular Weight (Monoisotopic): 452.0861

AlogP: 3.73

#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: 3.79

CX LogD: 3.75

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: 0.32

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