(2S,3R,4R,5S,6R)-2-(7-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-4-methoxy-2,3-dihydrobenzofuran-5-yl)-5-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

ID: ALA4279519

Chembl Id: CHEMBL4279519

PubChem CID: 137498470

Max Phase: Preclinical

Molecular Formula: C24H27FO8

Molecular Weight: 462.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c([C@@H]2O[C@H](CO)[C@@H](F)[C@H](O)[C@H]2O)cc(Cc2ccc3c(c2)OCCO3)c2c1CCO2

Standard InChI:  InChI=1S/C24H27FO8/c1-29-23-14-4-5-32-22(14)13(8-12-2-3-16-17(9-12)31-7-6-30-16)10-15(23)24-21(28)20(27)19(25)18(11-26)33-24/h2-3,9-10,18-21,24,26-28H,4-8,11H2,1H3/t18-,19-,20+,21-,24+/m1/s1

Standard InChI Key:  QUHJWCHBJBZVQP-IDYLKPADSA-N

Alternative Forms

1. Parent:

   

   ALA4279519

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 462.47

Molecular Weight (Monoisotopic): 462.1690

AlogP: 1.48

#Rotatable Bonds: 5

Polar Surface Area: 106.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.56

CX Basic pKa: ┄

CX LogP: 1.44

CX LogD: 1.44

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.61

Np Likeness Score: 1.04

References

1. Xu G, Gaul MD, Kuo GH, Du F, Xu JZ, Wallace N, Hinke S, Kirchner T, Silva J, Huebert ND, Lee S, Murray W, Liang Y, Demarest K..  (2018)  Design, synthesis and biological evaluation of (2S,3R,4R,5S,6R)-5-fluoro-6-(hydroxymethyl)-2-aryltetrahydro-2H-pyran-3,4-diols as potent and orally active SGLT dual inhibitors.,  28  (21): [PMID:30268701] [10.1016/j.bmcl.2018.09.025]

Source

Source(1):

• Scientific Literature