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

ID: ALA4789658

PubChem CID: 162669696

Max Phase: Preclinical

Molecular Formula: C22H24ClFO7

Molecular Weight: 454.88

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H24ClFO7/c1-22(24)18(10-25)31-20(19(27)21(22)28)13-8-12(14(23)9-15(13)26)6-11-2-3-16-17(7-11)30-5-4-29-16/h2-3,7-9,18-21,25-28H,4-6,10H2,1H3/t18-,19+,20+,21-,22-/m1/s1

Standard InChI Key:  YYMWHFACSHHXJW-CDJZJNNCSA-N

Molfile:  

 
     RDKit          2D

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   27.3677  -23.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5460  -23.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3677  -22.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0771  -24.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7865  -23.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7865  -22.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0771  -22.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4954  -22.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0771  -25.0316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6546  -22.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4936  -24.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6522  -21.7526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1985  -22.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9069  -22.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9098  -21.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1983  -21.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4928  -21.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6132  -22.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3223  -22.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0245  -23.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0250  -21.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3193  -21.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7363  -21.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7317  -22.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4308  -23.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1388  -22.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1434  -21.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4399  -21.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6181  -21.3570    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.7842  -21.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  1  0
  6  7  1  0
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  7  9  1  1
  5 10  1  1
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  6 12  1  6
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  9 14  2  0
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 19 20  1  0
 20 21  2  0
 21 25  1  0
 24 22  1  0
 22 23  2  0
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 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:

   

   ALA4789658

   ---

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: 454.88

Molecular Weight (Monoisotopic): 454.1195

AlogP: 2.29

#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: 2.29

CX LogD: 2.26

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: 0.76

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